text:
Talk:Amino acid

About AA's catabolic pathways
Regarding this piece: "After removal of one or more amino groups, the remainder of the molecule can sometimes be used to synthesize new amino acids, or it can be used for energy by entering glycolysis or the citric acid cycle, as detailed in image at right."

I think someone could add gluconeogenesis, at least, and maybe also the ketogenic pathways.
 * In fact, "the image at the right" puts it, so maybe someone could set it straight between text and image.

I also wasn't aware of aminoacids entering glycolysis, unless it was for gluconegoenesis, and the image on the right also doesn't show any support to it. In the end, it would be like: citric acid cycle, (glycolysis), ketogenesis, and gluconeogenesis

I just won't edit it by my own decision, I suppose.

--Orangutan45 (talk) 05:03, 24 May 2016 (UTC)

Zwiterionic AAs in the 21 AAs svg
Why are all the amino acids not shown in their zwitterionic forms in the main svg? At physiological 7.4 pH, this is what they would be, right? Moine Bouddhiste (talk) 12:28, 12 November 2016 (UTC)
 * Sure. But see among many other such discussions. DMacks (talk) 06:35, 14 November 2016 (UTC)
 * I could not open the link for #A question. I do feel that the amino acids should be shown at physiological pH. Unionized amino acids are not naturally found. D.Bhandal (talk) 19:21, 21 January 2019 (UTC)
 * The link is currently archived at Talk:Amino acid/Archive 3. Alexcalamaro (talk) 15:55, 22 August 2021 (UTC)
 * This doesn't seem to be fixed despite the question being raised in 2016. Unfortunately all the diagrams ought to be changed, but I don't know if I have the skill or energy to do that. The zwitterion section is like a biochemistry textbook of the 1960s: zwitterions are mentioned, because a physical chemist has said that they ought to be, but then the authors make it clear that they don't believe a word of it by going back to wrong structures for the rest of the book.  Athel cb (talk) 11:59, 14 September 2021 (UTC)
 * I added a note to the description stating it depicts the neutral instead of actual form, though ideally the file would be remade with the zwitterions. It's a bit weird when looking at the charged AAs', ie. Asp's side chain is deprotonated but the carboxyl group isn't, even though carboxyl's pKa is lower 30103db (talk) 19:13, 3 October 2023 (UTC)

Missing positive charge on NH of imidazol ring of histidine
Should there not be a positive charge on the NH of the imidazol ring of histidine at physiological pH? — Preceding unsigned comment added by Moine Bouddhiste (talk • contribs) 14:08, 12 November 2016 (UTC)
 * The table says that its sidechain is 90% neutral, only 10% in the charged form. DMacks (talk) 06:34, 14 November 2016 (UTC)
 * If the table says that then the table is, I feel sure, wrong. However, "feel sure" isn't good enough, but so far I haven't found a reliable source. I'll continue looking. I have a Merck Index in my office, and maybe it's there.  Athel cb (talk) 08:29, 15 September 2021 (UTC)
 * The diagram shows it as a member of the group of amino acids that have a positively charged side chain along with arginine and lysine, which implies that there is a positive charge on the side chain. But none is to be seen. It seems to be a clear case of self-contradiction. Polar Apposite (talk) 12:17, 19 December 2022 (UTC)

proline as an imino acid
This is old terminology. According to the IUPAC Gold Book, an imino acid needs to have both imine and carboxyl functional groups. Proline instead has a secondary amine group. Double sharp (talk) 11:26, 26 November 2016 (UTC)
 * Agreed, and Amino acid looks like a good explanation of current and historical details. The other sections need to be brought in line to relegate "imino" to a secondary detail. DMacks (talk) 03:20, 27 November 2016 (UTC)
 * as a starting point, do you agree with the §General structure statements? DMacks (talk) 03:32, 27 November 2016 (UTC)
 * Yes, that looks fine to me. Double sharp (talk) 03:58, 27 November 2016 (UTC)

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Lede needs a good edit
It's huge -- 555 words. That's surely too long. I don't have the interest or expertise, but hope someone else does. 60.248.185.19 (talk) 05:16, 1 June 2018 (UTC)
 * I have moved a large part of it to the biochemistry section, but it can probably be improved. Athel cb (talk) 12:28, 17 September 2021 (UTC)

d-Amino Acids: Toxic or Not?
I'm not sure how or where to put it, but some explanation of how d-amino acids interact with multi-cellular biochemistry should be included. I have found various references to "d-amino acids are toxic to humans" on the internet, but none of them explain how. The sources I have found that say that are mostly abstracts for biochemical papers, so I assume they know what they are talking about. Nevertheless, this article does not even contain the statement "D-amino acids are toxic to most life" or its converse "d-amino acids are benign to most life". 66.219.236.172 (talk) 07:11, 8 July 2018 (UTC)
 * Neither of those statements is blanket true, and we certainly couldn't say so without a cite to a reliable source. Some D-amino acids might be toxic by certain routes of exposure. There is comparably little of it in our diet (based on low occurance due to difficulty in biosynthesis). But some D-amino acids are found naturally in us as part of major biochemical processes (as discussed in the article). Feel free to post links to some abstracts. DMacks (talk) 14:00, 8 July 2018 (UTC)

This is entirely new to me (editing wikipedia). The section heading "D-amino acid natural abundance" is badly out of date. I recommend consulting a recent review article, Genchi, Giuseppe 2017. An overview on D-amino acids. Amino Acids, 49(9), pp.1521-1533. https://link.springer.com/article/10.1007/s00726-017-2459-5

It is open to the public and is very good. — Preceding unsigned comment added by Gary S. Hurd (talk • contribs) 18:31, 28 July 2019 (UTC)
 * welcome to Wikipedia! Please feel free to edit the article itself to update that section. In the mean time, I left a note there that the current content is not up-to-date. DMacks (talk) 20:07, 28 July 2019 (UTC)
 * {Maybe that ref should go into D-Amino acid, which would benefit from some additional editing.--Smokefoot (talk) 02:08, 29 July 2019 (UTC)

Copyright violation?
Some Human Genetic Disorders Affecting Amino Acid Catabolism is a recently created subsection with a table, under Catabolism. Is it possible that the table was copied verbatim from the reference: Jain, J. L. Fundamentals of biochemistry. New Delhi: S. Chand and Co. ISBN 8121903432. OCLC 818809626. David notMD (talk) 09:24, 25 September 2019 (UTC)
 * One of a pool of presumably student editors, with poor contribution habits. I object editorially, as being too specialized/detailed for this main "amino acid" article, so I'm removing it. DMacks (talk) 03:35, 9 December 2019 (UTC)

Better words
May I suggest this improved version of the first sentence in the second paragraph that begins,'In biochemistry, amino acids having both the amine and the carboxylic acid groups attached to the first (alpha-) carbon atom have particular importance.'

In biochemistry, because amino acids have both the amine and carboxylic acid groups attached to the first (alph-) carbon atom they have particular importance.

Or better still,

Amino acids have both the amine and carboxylic acid groups attached to the first (alph-) carbon atom making them particularly importance in biochemistry.

I am not game to edit things directly, but a lot of Science articles are less well written than they could be. We live in a shockingly polarised world where people stream their education and end up either Literate or Numerate, but rarely both.

Of course, the second Paragraph begins with essentially the same content as the first, which is very poetic, but extends the article making it daunting to read. Yet it is of such fundamental importance. We are mostly made of two things and this is about one of them. There is so much to think about on so many levels and in so many dimensions. See!! I am not reading it now.

NaumTered 22:18, 28 August 2020 (UTC) — Preceding unsigned comment added by Norm Tered (talk • contribs)
 * Both of your suggestions change the meaning of the original sentence, which is wrong anyway. It claims that alpha amino acids have both groups on the same carbon, but the alpha carbon is in fact the one next to the carboxyl carbon. I'll change this. Further, you may claim that scientists are 'illiterate', but your prose contains basic errors. E.g. "begins,'In", "(alph-)", "(alph-)", "particularly importance". Zato123 (talk) 04:33, 14 September 2020 (UTC)

 * The alpha carbon is carbon number 2, which is a little bit confusing. It is called "alpha" because it is the first carbon in the side chain, and called "2" because it is the second carbon in the longest carbon chain in the molecule. So it's actually true that the carboxyl group (but not "the carboxylic acid group", which might not even exist as a correct term) is attached to the alpha carbon in amino acids.
 * On the other hand, since *all* amino acids are like this, by definition, it makes little sense to say that this type of amino acid "has particular importance".
 * Searching the article for "particular importance" yielded nothing so it seems this error has been corrected. Polar Apposite (talk) 14:21, 20 November 2022 (UTC)
 * Amino acids need not be alpha. Beta-alanine is the simplest one that is not. But it's the alpha series that are especially important biochemically. DMacks (talk) 18:39, 20 November 2022 (UTC)
 * I think you're right. Thank you for educating me. Maybe I was a bit tired and in a rush when I wrote that comment, or confused by all the errors in the text I was commenting on. I mean, I think I knew that, but I forgot, for some reason.
 * Googling around, I see that my error is a common one, for example: https://bio.libretexts.org/Courses/University_of_California_Davis/BIS_2A%3A_Introductory_Biology_(Easlon)/Readings/04.3%3A_Amino_Acids has "Amino acids are the monomers that make up proteins. Each amino acid has the same core structure, which consists of a central carbon atom, also known as the alpha (α) carbon, bonded to an amino group (NH2), a carboxyl group (COOH), and a hydrogen atom. Every amino acid also has another atom or group of atoms bonded to the alpha carbon known alternately as the R group, the variable group or the side-chain."
 * Also, https://www.britannica.com/science/amino-acid has "amino acid, any of a group of organic molecules that consist of a basic amino group (―NH2), an acidic carboxyl group (―COOH), and an organic R group (or side chain) that is unique to each amino acid. The term amino acid is short for α-amino [alpha-amino] carboxylic acid. Each molecule contains a central carbon (C) atom, called the α-carbon, to which both an amino and a carboxyl group are attached. The remaining two bonds of the α-carbon atom are generally satisfied by a hydrogen (H) atom and the R group." Polar Apposite (talk) 04:01, 21 November 2022 (UTC)

'amino acid residues' -- link more directly to what it means in this context?
In the lead, in the sentence, "In the form of proteins, amino acid residues form the second-largest component...", would it be ok to link the whole term 'amino acid residues' (as I have done here) to the specific sub-section in the chemistry article which does eventually explain 'residue' in a biochemical/protein context, instead of as it is currently, which just links the single word 'residues' to the whole chemistry article about residues in general? That article starts by giving a more general definition of 'residue', which general definition could initially be confusing to some. Further on down in that article is the relevant sub-section which defines residue in a more protein-relevant manner, and that's what I would think to link directly to. UnderEducatedGeezer (talk) 04:36, 28 December 2020 (UTC)
 * Unless it might be better to link the phrase to the sub-section immediately before the biochem sub-section, Residue_(chemistry)? UnderEducatedGeezer (talk) 04:41, 28 December 2020 (UTC)

Main figure should probably be an L-amino acid
The amino acid in the main figure had D configuration. This might be confusing for some readers as mostly L-amino acids are used in biology, industry, research etc. I myself tried to figure if the stereoisomer I drew is in the correct configuration by comparing to that image. Luckily I compared also with other sources. 185.175.34.246 (talk) 12:03, 13 June 2021 (UTC)
 * Excellent point! ✅--Smokefoot (talk) 19:01, 13 June 2021 (UTC)
 * just me, or are the newly added image another image with D configuration? Christian75 (talk) 14:51, 24 August 2023 (UTC)

So much to do, so little time
There are a great many things to be corrected in this article and I plan to do some serious editing in the next few days or weeks. I'm mentioning it here because some experts will disagree with my edits, and I want to give them the opportunity to say so. Ideally, many of the figures should be redrawn, but I'm not sure that I have the skill for that. Athel cb (talk) 09:18, 15 September 2021 (UTC)
 * What are some of the big problems? Given the generality of the topic, we should rely on secondary or even tertiary sources, like textbooks.--Smokefoot (talk) 13:43, 16 September 2021 (UTC)
 * The most serious problems concern ionization, a topic vital for understanding amino acid chemistry, but which the author of the section on zwitterions clearly did not understand. Unfortunately this affects the whole article, including most of the figures.  Athel cb (talk) 11:38, 17 September 2021 (UTC)

Toxicity: any suggested source?
Stimulated by the question above about toxicity of D-amino acids I have been searching for a reliable source of information. I have located my Merck Index, but it does not include systematic information about that. Likewise the Rubber Book and two encyclopaedias of biochemistry that I have. I have searched Web of Science for "LD-50" AND "amino acid" and similar search strings, but although I get vast numbers of hits I haven't found anything useful. Yet there has to be a table somewhere on LD-50 values. Any suggestions? Athel cb (talk) 13:29, 21 September 2021 (UTC)

Cationic side-chains
In the figure for cationic side-chains, the fixed cation on the arginine side chain should read H2N+= rather than H3N+=. Citation: Wikipedia's own Arginine entry, among many others. — Preceding unsigned comment added by 99.165.76.203 (talk) 14:44, 9 November 2021 (UTC)

 * "NH2 + " doesn't exist. Nitrogen in NH2 can have positive charge only if it accepts a proton, since the amino group acts as a small Brønsted base, thereby becoming the Ammonium (NH3 + ) cation. This is just simple acid-base theory. — CrafterNova [ TALK ]  [ CONT ] 17:48, 7 May 2022 (UTC)
 * IP 99 is actually correct here. They state correctly that the N in question in File:Side-chains of His, Lys and Arg.png is the one with a double-bond to the central C, the iminium-like portion. I think you are reading it to be about the N with one bond, the ammonium-like portion? An N with two bonds and 3 H would exceed octet; an iminium only has two H. DMacks (talk) 19:42, 7 May 2022 (UTC)
 * this is your image, and is consistent with several others of yours, such as File:Ionization of groups in proteins.png. Any thoughts? DMacks (talk) 19:45, 7 May 2022 (UTC)
 * Yes, you're right. I need to change the image. (I hope that won't mean redrawing it completely, as I don't know if I have the original file somewhere.) Maddeningly, I had it correct in the 4th edition of Fundamentals of Enzyme Kinetics -- the error must have arisen in converting the monochrome version to colour. Athel cb (talk) 08:22, 8 May 2022 (UTC)
 * For the moment I've just deleted the image as a stop-gap measure.  Athel cb (talk) 08:33, 8 May 2022 (UTC)
 * Now done: corrected file uploaded.  Athel cb (talk) 09:30, 8 May 2022 (UTC)

Nomenclature description in lead section
Beginning at the second paragraph, there's a fairly editorial description of UIPAC naming convention that puts too much weight on the rarity of the structure in nature. Especially the word "fictitious," use of scare quotes, and repeating part of a probably unnecessary quote. Same bias seems to affect the caption. This may be an important issue, but deserves at most a brief mention in the lead. At least that's how it struck me. Yellowdesk60 (talk) 17:43, 2 January 2022 (UTC)

what
I quote:

 * The first few amino acids were discovered in the early 1900s.[6][7] In 1806, French chemists Louis-Nicolas Vauquelin and Pierre Jean Robiquet isolated a compound from asparagus that was subsequently named asparagine, the first amino acid to be discovered.[8][9] Cystine was discovered in 1810,[10] although its monomer, cysteine, remained undiscovered until 1884.[11][9][b] Glycine and leucine were discovered in 1820.[12]

Isn't that an immediate contradiction? How could "the first few" amino acids have been discovered in the "early 1900s" when several were discovered in the previous century? --123.243.244.238 (talk) 10:24, 3 March 2022 (UTC)

 * You would seem to be correct. It seems to have been corrected. Arctic Gazelle (talk) 19:36, 25 April 2022 (UTC)

"Aspartic/Glutamic Acid" vs "Aspartate/Glutamate"
At certain points, the article becomes unusually passionate about this notion that the names "aspartic acid" and "glutamic acid" are incorrect (see the "Anionic side-chains" subsection) and that the only correct names are "aspartate" and "glutamate". It currrently says about the acid names: "Although the misnomer is so widespread as to be ineradicable, they should not be called acidic amino acids, because they act as Brønsted bases in all circumstances except for enzymes like pepsin that act in environments of very low pH like the mammalian stomach." (bold/italic emphasis already there in the article)

I'd like the opinion of other (bio)chemists on this. I call this overly pedantic. I want to point out that this choice is inconsistent with the names of their corresponding Wikipedia pages (currently Aspartic acid and Glutamic acid), and that the acid names are used regularly in the primary and secondary literature by (bio)chemists themselves without controversy. Also, many students are likely to encounter the acid names in their first exposures. We do not emphasize that "amino acids" are "ammonium carboxylates" at all physiological pH values or that "arginine" is "argininium", and I think these would be similarly correct-yet-too-pedantic changes to make.

In the meantime, I will edit the tone to be less aggressively "anti-acid" because I think it does not contribute to the helpfulness of the article more than a neutral discussion of nomenclature would. TungstenEinsteinium (talk) 18:30, 2 May 2022 (UTC)

 * The distinction between -ate and acid is technically correct as there is a difference between the two terms, though it's usually still obvious from the pH what you mean if you use the wrong one. Aspartate and glutamate are the deprotonated forms of aspartic and glutamic acid. The deprotonated form (aspartate) is most common at physiological pH, but the protonated form (aspartic acid) exists in acidic environments. Since physiological pH is simply implied a lot of the time, colloquially the terms end up being used interchangeably.
 * I think the names should not be used interchangeably in the article, because people may mistakenly believe both forms are equivalent. It may also lead to awkward wording such as "anionic glutamate" when distinguishing between the two. In my opinion, "aspartate/glutamate" should be used as the default terms when discussing amino acids as they naturally occur, unless specifically referring to the protonated form. In the svg file of the 21 amino acids, they should definitely be labeled "Aspartate/Glutamate" and not "Aspartic/Glutamic Acid", as they're categorized as having charged side chains and only the prior is charged. 30103db (talk) 20:25, 3 October 2023 (UTC)

Update needed for number of amino acids in genetic code

 * "More than 500 naturally occurring amino acids are known to constitute monomer units of peptides, including proteins, as of 2020 (though only 20 [needs update] appear in the genetic code, plus selenocysteine, which is encoded in a special way).

This sentence is outdated. Some sources there are actually 22 amino acids which participate in in-vivo protein synthesis, listed below: — CrafterNova [ TALK ]  [ CONT ] 17:23, 7 May 2022 (UTC)
 * Comparing the article "20 appear in the genetic code " with your second ref "selenocysteine and pyrrolysine are considered the 21st and 22nd amino acids, respectively. They are more recently discovered amino acids that may become incorporated into protein chains during ribosomal protein synthesis ", I think the appearance of contradiction is the result of a slight difference of words. Selenocysteine and pyrrolysine do not have their own DNA codons, but instead result from a different post-transcriptional handling of stop codons. So they are 22 proteinogenic amino acids, of which two are incorporated by processes other than the standard genetic code. However, your first ref does directly state that selenocysteine is "genetically encoded".
 * Pyrrolysine is only found in certain procaryotes. And synthetic biology has led to production of codons to incorporate amino acids that are not found in any ribosomally-produced proteins.
 * So first, we definitely need to add pyrrolysine as the 22nd when we mention selenocysteine as the 21st and clarify that we are talking about what's found currently in naturee, or else clarify that our discussion of 21 is based on certain categories of organisms found in nature. Second, we need to distinguish these two as slightly different from the other 20, while also keeping this key introduction understandable without needing to know technical terms. DMacks (talk) 17:54, 7 May 2022 (UTC)

Please update with: "Prebiotic synthesis of α-amino acids and orotate from α-ketoacids potentiates transition to extant metabolic pathways" & info on relation to abiogenesis
I think it may be good to add at least very brief info from/about this study and/or similar articles to the article. It's currently featured in 2022 in science like so:

"Scientists report the discovery of chemical reactions by potential primordial soup components that produced amino acids and may be part of the origin of life on Earth."

More generally and beyond this study in specific, please add some info about how amino acids are thought to relate to the origin of life on Earth (abiogenesis) and are thought to originate, including with some brief info in the lead. I find it strange that this seems to be entirely missing in the article if I haven't only overlooked it.

Useful sources for this may include: "Amino acids and the origin of life on Earth", "The origin of the biologically coded amino acids", "Undefining life's biochemistry: implications for abiogenesis" and "Small Cofactors May Assist Protein Emergence from RNA World: Clues from RNA-Protein Complexes".

Prototyperspective (talk) 17:16, 2 September 2022 (UTC)
 * The article on amino acids is already long. It is appropriately focused on present day biochemistry.  Per WP:NOTNEWS, Wikipedia shies away from "hot papers", especially when they are somewhat tangential.  The targetted refs are WP:SECONDARY (reviews) and even better WP:TERTIARY (textbooks).  --Smokefoot (talk) 19:44, 2 September 2022 (UTC)
 * If the article on amino acids doesn't even at least mention abiogenesis / the origin of life with at least a few words (doesn't have to be long), something critical (basically right in the core of the article's topic), is very clearly missing.
 * Otherwise, that is / may be a fair point – however, you could also add this info via a review (or some reviews and/or textbooks) here and I also linked some as "Useful sources" above. Prototyperspective (talk) 20:57, 2 September 2022 (UTC)
 * Oh, I see your point. Sorry to seem obstructionist.  We definitely need something beyond a mere link to the Miller–Urey experiment.  There must be books and many reviews on this topic. I also will look around. --Smokefoot (talk) 22:13, 2 September 2022 (UTC)
 * Please take a look and improve!--Smokefoot (talk) 00:01, 3 September 2022 (UTC)
 * Done. Most striking to me was the lack of at least a wikilink to the abiogenesis article and that a mention was still missing in the lead. Some of the content I added may need some copyediting and I may have phrased some things a bit inadequately. That's partly why I asked about it on the Talk page anyway. Moreover, now I haven't used any of the sources I proposed here which somebody else may still find useful to add if the content can get condensed. Prototyperspective (talk) 21:15, 5 September 2022 (UTC)

The General Structure section diagram needs clarification.
The diagram shows histadine without a charge on its side chain, but it is lumped in with Group A. Conversely, selenocysteine is shown with a charge on its side chain and yet is *not* in Group A. I would like to know why, and I think a lot of readers would. Also, I'd like to know what "Special Cases" (defining Group C) means. How about clarification regarding this in the caption to the diagram? Polar Apposite (talk) 10:12, 15 November 2022 (UTC)

The side chains do not ionize *because* they contain only H and C?
I edited the aliphatic side-chains section. I added "therefore" to "do not ionize", reversed the positions of isoleucine and leucine to match the General Structure chart, and added phenylalanine. I am a layman so I would appreciate a chemist checking my work here. Polar Apposite (talk) 17:29, 17 November 2022 (UTC)

 * Is it supposed to say that the amino acids do not ionize, or the side chains do not ionize? Polar Apposite (talk) 17:38, 17 November 2022 (UTC)

Hydrophobicity
It says, "The water-soluble proteins tend to have their hydrophobic residues (Leu, Ile, Val, Phe, and Trp) buried in the middle of the protein, whereas hydrophilic side chains are exposed to the aqueous solvent." 1. Shouldn't the full names rather than the three-letter symbols be used? 2. Can a residue with a hydrophobic side chain not be hydrophobic? If so, is like being compared to like when a list of residues is contrasted with a type of side chain? 3. Is it the hydrophobic side chain that tends to be buried in the middle of the protein, or the whole residue? 4. The diagram near the top of the article lists *eight* hydrophobic (with a hydrophobic side chain, if that's different) amino acids, so is that list of five correct? Polar Apposite (talk) 18:15, 19 December 2022 (UTC)

Grouped how?
It says in the caption to the color chart,"The 21 proteinogenic α-amino acids found in eukaryotes, grouped according to their side chains' pKa values and charges carried at physiological pH (7.4)" but the pKa values of most of the side chains of the alpha-amino acids are not shown, and it very much looks to me that they are grouped according to hydrophobicity, and so on, as it says in the chart and ordered according to increasing complexity going from left to right, at least in the section containing the eight amino acids classified as having a hydrophobic side chain. Furthermore, in the few cases where the pKa value of the side chain is shown, there is no grouping according pKa value that I can see. Arg, His, and Lys are in the one group but the pKa value of the side chain is 12.10, 6.04, 10.67 respectively, while Tyr, which has a side chain pKa of 10.10, which would seem to indicate that it should be grouped with those three is instead in another group. Polar Apposite (talk) 16:55, 10 January 2023 (UTC)

Section removed
The following section was removed because it did not appear to fit in with the main theme, amino acids, but maybe I am mistaken:

Dietary exposure to the nonstandard amino acid BMAA has been linked to human neurodegenerative diseases, including ALS.

--Smokefoot (talk) 18:15, 29 September 2023 (UTC)

title: Talk:Amino acid


text:
Amine

In chemistry, amines (, UK also  ) are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Formally, amines are derivatives of ammonia (NH3), wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group (these may respectively be called alkylamines and arylamines; amines in which both types of substituent are attached to one nitrogen atom may be called alkylarylamines). Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine (NClH2).

The substituent \sNH2 is called an amino group.

Compounds with a nitrogen atom attached to a carbonyl group, thus having the structure R\sC(\dO)\sNR′R″, are called amides and have different chemical properties from amines.

Classification of amines
Amines can be classified according to the nature and number of substituents on nitrogen. Aliphatic amines contain only H and alkyl substituents. Aromatic amines have the nitrogen atom connected to an aromatic ring.

 * Primary (1°) amines—Primary amines arise when one of three hydrogen atoms in ammonia is replaced by an alkyl or aromatic group. Important primary alkyl amines include methylamine, most amino acids, and the buffering agent tris, while primary aromatic amines include aniline.
 * Secondary (2°) amines—Secondary amines have two organic substituents (alkyl, aryl or both) bound to the nitrogen together with one hydrogen. Important representatives include dimethylamine, while an example of an aromatic amine would be diphenylamine.
 * Tertiary (3°) amines—In tertiary amines, nitrogen has three organic substituents. Examples include trimethylamine, which has a distinctively fishy smell, and EDTA.

A fourth subcategory is determined by the connectivity of the substituents attached to the nitrogen:

 * Cyclic amines—Cyclic amines are either secondary or tertiary amines. Examples of cyclic amines include the 3-membered ring aziridine and the six-membered ring piperidine. N-methylpiperidine and N-phenylpiperidine are examples of cyclic tertiary amines.

It is also possible to have four organic substituents on the nitrogen. These species are not amines but are quaternary ammonium cations and have a charged nitrogen center. Quaternary ammonium salts exist with many kinds of anions.

Naming conventions
Amines are named in several ways. Typically, the compound is given the prefix "amino-" or the suffix "-amine". The prefix "N-" shows substitution on the nitrogen atom. An organic compound with multiple amino groups is called a diamine, triamine, tetraamine and so forth.

Lower amines are named with the suffix -amine. Higher amines have the prefix amino as a functional group. IUPAC however does not recommend this convention, but prefers the alkanamine form, e.g. butan-2-amine.

Physical properties
Hydrogen bonding significantly influences the properties of primary and secondary amines. For example, methyl and ethyl amines are gases under standard conditions, whereas the corresponding methyl and ethyl alcohols are liquids. Amines possess a characteristic ammonia smell, liquid amines have a distinctive "fishy" and foul smell.

The nitrogen atom features a lone electron pair that can bind H+ to form an ammonium ion R3NH+. The lone electron pair is represented in this article by two dots above or next to the N. The water solubility of simple amines is enhanced by hydrogen bonding involving these lone electron pairs. Typically salts of ammonium compounds exhibit the following order of solubility in water: primary ammonium > secondary ammonium  > tertiary ammonium (R3NH+). Small aliphatic amines display significant solubility in many solvents, whereas those with large substituents are lipophilic. Aromatic amines, such as aniline, have their lone pair electrons conjugated into the benzene ring, thus their tendency to engage in hydrogen bonding is diminished. Their boiling points are high and their solubility in water is low.

Spectroscopic identification
Typically the presence of an amine functional group is deduced by a combination of techniques, including mass spectrometry as well as NMR and IR spectroscopies. 1H NMR signals for amines disappear upon treatment of the sample with D2O. In their infrared spectrum primary amines exhibit two N-H bands, whereas secondary amines exhibit only one. In their IR spectra, primary and secondary amines exhibit distinctive N-H stretching bands near 3300 cm-1. Somewhat less distinctive are the bands appearing below 1600 cm-1, which are weaker and overlap with C-C and C-H modes. For the case of propyl amine, the H-N-H scissor mode appears near 1600 cm-1, the C-N stretch near 1000 cm-1, and the R2N-H bend near 810 cm-1.

Alkyl amines
Alkyl amines characteristically feature tetrahedral nitrogen centers. C-N-C and C-N-H angles approach the idealized angle of 109°. C-N distances are slightly shorter than C-C distances. The energy barrier for the nitrogen inversion of the stereocenter is about 7 kcal/mol for a trialkylamine. The interconversion has been compared to the inversion of an open umbrella into a strong wind.

Amines of the type NHRR' and NRR′R″ are chiral: the nitrogen center bears four substituents counting the lone pair. Because of the low barrier to inversion, amines of the type NHRR' cannot be obtained in optical purity. For chiral tertiary amines, NRR′R″ can only be resolved when the R, R', and R″ groups are constrained in cyclic structures such as N-substituted aziridines (quaternary ammonium salts are resolvable).

Aromatic amines
In aromatic amines ("anilines"), nitrogen is often nearly planar owing to conjugation of the lone pair with the aryl substituent. The C-N distance is correspondingly shorter. In aniline, the C-N distance is the same as the C-C distances.

Basicity
Like ammonia, amines are bases. Compared to alkali metal hydroxides, amines are weaker.

The basicity of amines depends on:
 * 1) The electronic properties of the substituents (alkyl groups enhance the basicity, aryl groups diminish it).
 * 2) The degree of solvation of the protonated amine, which includes steric hindrance by the groups on nitrogen.

Electronic effects
Owing to inductive effects, the basicity of an amine might be expected to increase with the number of alkyl groups on the amine. Correlations are complicated owing to the effects of solvation which are opposite the trends for inductive effects. Solvation effects also dominate the basicity of aromatic amines (anilines). For anilines, the lone pair of electrons on nitrogen delocalizes into the ring, resulting in decreased basicity. Substituents on the aromatic ring, and their positions relative to the amino group, also affect basicity as seen in the table.

Solvation effects
Solvation significantly affects the basicity of amines. N-H groups strongly interact with water, especially in ammonium ions. Consequently, the basicity of ammonia is enhanced by 1011 by solvation. The intrinsic basicity of amines, i.e. the situation where solvation is unimportant, has been evaluated in the gas phase. In the gas phase, amines exhibit the basicities predicted from the electron-releasing effects of the organic substituents. Thus tertiary amines are more basic than secondary amines, which are more basic than primary amines, and finally ammonia is least basic. The order of pKb's (basicities in water) does not follow this order. Similarly aniline is more basic than ammonia in the gas phase, but ten thousand times less so in aqueous solution.

In aprotic polar solvents such as DMSO, DMF, and acetonitrile the energy of solvation is not as high as in protic polar solvents like water and methanol. For this reason, the basicity of amines in these aprotic solvents is almost solely governed by the electronic effects.

From alcohols
Industrially significant alkyl amines are prepared from ammonia by alkylation with alcohols:

From alkyl and aryl halides
Unlike the reaction of amines with alcohols the reaction of amines and ammonia with alkyl halides is used for synthesis in the laboratory:

In such reactions, which are more useful for alkyl iodides and bromides, the degree of alkylation is difficult to control such that one obtains mixtures of primary, secondary, and tertiary amines, as well as quaternary ammonium salts.

Selectivity can be improved via the Delépine reaction, although this is rarely employed on an industrial scale. Selectivity is also assured in the Gabriel synthesis, which involves organohalide reacting with potassium phthalimide.

Aryl halides are much less reactive toward amines and for that reason are more controllable. A popular way to prepare aryl amines is the Buchwald-Hartwig reaction.

From alkenes
Disubstituted alkenes react with HCN in the presence of strong acids to give formamides, which can be decarbonylated. This method, the Ritter reaction, is used industrially to produce tertiary amines such as tert-octylamine.

Hydroamination of alkenes is also widely practiced. The reaction is catalyzed by zeolite-based solid acids.

Reductive routes
Via the process of hydrogenation, unsaturated N-containing functional groups are reduced to amines using hydrogen in the presence of a nickel catalyst. Suitable groups include nitriles, azides, imines including oximes, amides, and nitro. In the case of nitriles, reactions are sensitive to acidic or alkaline conditions, which can cause hydrolysis of the \sCN group. LiAlH4 is more commonly employed for the reduction of these same groups on the laboratory scale.

Many amines are produced from aldehydes and ketones via reductive amination, which can either proceed catalytically or stoichiometrically.

Aniline (C6H5NH2) and its derivatives are prepared by reduction of the nitroaromatics. In industry, hydrogen is the preferred reductant, whereas, in the laboratory, tin and iron are often employed.

Specialized methods
Many methods exist for the preparation of amines, many of these methods being rather specialized.

Alkylation, acylation, and sulfonation, etc.
Aside from their basicity, the dominant reactivity of amines is their nucleophilicity. Most primary amines are good ligands for metal ions to give coordination complexes. Amines are alkylated by alkyl halides. Acyl chlorides and acid anhydrides react with primary and secondary amines to form amides (the "Schotten–Baumann reaction"). Similarly, with sulfonyl chlorides, one obtains sulfonamides. This transformation, known as the Hinsberg reaction, is a chemical test for the presence of amines.

Because amines are basic, they neutralize acids to form the corresponding ammonium salts R3NH+. When formed from carboxylic acids and primary and secondary amines, these salts thermally dehydrate to form the corresponding amides.

Amines undergo sulfamation upon treatment with sulfur trioxide or sources thereof:

Diazotization
Amines reacts with nitrous acid to give diazonium salts. The alkyl diazonium salts are of little importance because they are too unstable. The most important members are derivatives of aromatic amines such as aniline ("phenylamine") (A = aryl or naphthyl):

Anilines and naphthylamines form more stable diazonium salts, which can be isolated in the crystalline form. Diazonium salts undergo a variety of useful transformations involving replacement of the N2 group with anions. For example, cuprous cyanide gives the corresponding nitriles:

Aryldiazoniums couple with electron-rich aromatic compounds such as a phenol to form azo compounds. Such reactions are widely applied to the production of dyes.

Conversion to imines
Imine formation is an important reaction. Primary amines react with ketones and aldehydes to form imines. In the case of formaldehyde (R' = H), these products typically exist as cyclic trimers.

Reduction of these imines gives secondary amines:

Similarly, secondary amines react with ketones and aldehydes to form enamines:

Overview
An overview of the reactions of amines is given below:

Biological activity
Amines are ubiquitous in biology. The breakdown of amino acids releases amines, famously in the case of decaying fish which smell of trimethylamine. Many neurotransmitters are amines, including epinephrine, norepinephrine, dopamine, serotonin, and histamine. Protonated amino groups are the most common positively charged moieties in proteins, specifically in the amino acid lysine. The anionic polymer DNA is typically bound to various amine-rich proteins. Additionally, the terminal charged primary ammonium on lysine forms salt bridges with carboxylate groups of other amino acids in polypeptides, which is one of the primary influences on the three-dimensional structures of proteins.

Amine hormones
Hormones derived from the modification of amino acids are referred to as amine hormones. Typically, the original structure of the amino acid is modified such that a –COOH, or carboxyl, group is removed, whereas the, or amine, group remains. Amine hormones are synthesized from the amino acids tryptophan or tyrosine.

Dyes
Primary aromatic amines are used as a starting material for the manufacture of azo dyes. It reacts with nitrous acid to form diazonium salt, which can undergo coupling reaction to form an azo compound. As azo-compounds are highly coloured, they are widely used in dyeing industries, such as:

 * Methyl orange
 * Direct brown 138
 * Sunset yellow FCF
 * Ponceau

Drugs
Most drugs and drug candidates contain amine functional groups:
 * Chlorpheniramine is an antihistamine that helps to relieve allergic disorders due to cold, hay fever, itchy skin, insect bites and stings.
 * Chlorpromazine is a tranquilizer that sedates without inducing sleep. It is used to relieve anxiety, excitement, restlessness or even mental disorder.
 * Ephedrine and phenylephrine, as amine hydrochlorides, are used as decongestants.
 * Amphetamine, methamphetamine, and methcathinone are psychostimulant amines that are listed as controlled substances by the US DEA.
 * Thioridazine, an antipsychotic drug, is an amine which is believed to exhibit its antipsychotic effects, in part, due to its effects on other amines.
 * Amitriptyline, imipramine, lofepramine and clomipramine are tricyclic antidepressants and tertiary amines.
 * Nortriptyline, desipramine, and amoxapine are tricyclic antidepressants and secondary amines. (The tricyclics are grouped by the nature of the final amino group on the side chain.)
 * Substituted tryptamines and phenethylamines are key basic structures for a large variety of psychedelic drugs.
 * Opiate analgesics such as morphine, codeine, and heroin are tertiary amines.

Gas treatment
Aqueous monoethanolamine (MEA), diglycolamine (DGA), diethanolamine (DEA), diisopropanolamine (DIPA) and methyldiethanolamine (MDEA) are widely used industrially for removing carbon dioxide (CO2) and hydrogen sulfide (H2S) from natural gas and refinery process streams. They may also be used to remove CO2 from combustion gases and flue gases and may have potential for abatement of greenhouse gases. Related processes are known as sweetening.

Epoxy resin curing agents
Amines are often used as epoxy resin curing agents. These include dimethylethylamine, cyclohexylamine, and a variety of diamines such as 4,4-diaminodicyclohexylmethane. Multifunctional amines such as tetraethylenepentamine and triethylenetetramine are also widely used in this capacity. The reaction proceeds by the lone pair of electrons on the amine nitrogen attacking the outermost carbon on the oxirane ring of the epoxy resin. This relieves ring strain on the epoxide and is the driving force of the reaction. Molecules with tertiary amine functionality are often used to accelerate the epoxy-amine curing reaction and include substances such as 2,4,6-Tris(dimethylaminomethyl)phenol. It has been stated that this is the most widely used room temperature accelerator for two-component epoxy resin systems.

Safety
Low molecular weight simple amines, such as ethylamine, are only weakly toxic with between 100 and 1000 mg/kg. They are skin irritants, especially as some are easily absorbed through the skin. Amines are a broad class of compounds, and more complex members of the class can be extremely bioactive, for example strychnine.

license: Creative Commons - Attribution Share-Alike - https://creativecommons.org/licenses/by-sa/4.0/

title: Amine


text:
April 29

Pre-1600

 * 801 – An earthquake in the Central Apennines hits Rome and Spoleto, damaging the basilica of San Paolo Fuori le Mura.
 * 1091 – Battle of Levounion: The Pechenegs are defeated by Byzantine Emperor Alexios I Komnenos.
 * 1429 – Joan of Arc arrives to relieve the Siege of Orléans.
 * 1483 – Gran Canaria, the main island of the Canary Islands, is conquered by the Kingdom of Castile.
 * 1521 – Swedish War of Liberation: Swedish troops defeat a Danish force in the Battle of Västerås.

1601–1900

 * 1760 – French forces commence the siege of Quebec which is held by the British.
 * 1770 – James Cook arrives in Australia at Botany Bay, which he names.
 * 1781 – American Revolutionary War: British and French ships clash in the Battle of Fort Royal off the coast of Martinique.
 * 1826 – The galaxy Centaurus A or NGC 5128 is discovered by James Dunlop.
 * 1861 – Maryland in the American Civil War: Maryland's House of Delegates votes not to secede from the Union.
 * 1862 – American Civil War: The Capture of New Orleans by Union forces under David Farragut.
 * 1864 – Theta Xi fraternity is founded at Rensselaer Polytechnic Institute, the only fraternity to be founded during the American Civil War.

1901–present

 * 1903 – A landslide kills 70 people in Frank, in the District of Alberta, Canada.
 * 1910 – The Parliament of the United Kingdom passes the People's Budget, the first budget in British history with the expressed intent of redistributing wealth among the British public.
 * 1911 – Tsinghua University, one of mainland China's leading universities, is founded.
 * 1916 – World War I: The UK's 6th Indian Division surrenders to Ottoman Forces at the Siege of Kut in one of the largest surrenders of British forces up to that point.
 * 1916  – Easter Rising: After six days of fighting, Irish rebel leaders surrender to British forces in Dublin, bringing the Easter Rising to an end.
 * 1945 – World War II: The Surrender of Caserta is signed by the commander of German forces in Italy.
 * 1945  – World War II: Airdrops of food begin over German-occupied regions of the Netherlands.
 * 1945  – World War II: Adolf Hitler marries his longtime partner Eva Braun in a Berlin bunker and designates Admiral Karl Dönitz as his successor.
 * 1945  – Dachau concentration camp is liberated by United States troops.
 * 1946 – The International Military Tribunal for the Far East convenes and indicts former Prime Minister of Japan Hideki Tojo and 28 former Japanese leaders for war crimes.
 * 1952 – Pan Am Flight 202 crashes into the Amazon basin near Carolina, Maranhão, Brazil, killing 50 people.
 * 1953 – The first U.S. experimental 3D television broadcast shows an episode of Space Patrol on Los Angeles ABC affiliate KECA-TV.
 * 1967 – After refusing induction into the United States Army the previous day, Muhammad Ali is stripped of his boxing title.
 * 1970 – Vietnam War: United States and South Vietnamese forces invade Cambodia to hunt Viet Cong.
 * 1974 – Watergate scandal: United States President Richard Nixon announces the release of edited transcripts of White House tape recordings relating to the scandal.
 * 1975 – Vietnam War: Operation Frequent Wind: The U.S. begins to evacuate U.S. citizens from Saigon before an expected North Vietnamese takeover. U.S. involvement in the war comes to an end.
 * 1975  – Vietnam War: The North Vietnamese army completes its capture of all parts of South Vietnam-held Trường Sa Islands.
 * 1986 – A fire at the Central library of the Los Angeles Public Library damages or destroys 400,000 books and other items.
 * 1986 – The United States Navy aircraft carrier USS Enterprise (CVN-65) becomes the first nuclear-powered aircraft carrier to transit the Suez Canal, navigating from the Red Sea to the Mediterranean Sea to relieve the USS Coral Sea (CV-43).
 * 1991 – A cyclone strikes the Chittagong district of southeastern Bangladesh with winds of around 155 mph, killing at least 138,000 people and leaving as many as ten million homeless.
 * 1991  – The 7.0  Racha earthquake affects Georgia with a maximum MSK intensity of IX (Destructive), killing 270 people.
 * 1992 – Riots in Los Angeles begin, following the acquittal of police officers charged with excessive force in the beating of Rodney King. Over the next three days 63 people are killed and hundreds of buildings are destroyed.
 * 1997 – The Chemical Weapons Convention of 1993 enters into force, outlawing the production, stockpiling and use of chemical weapons by its signatories.
 * 2004 – The final Oldsmobile is built in Lansing, Michigan, ending 107 years of vehicle production.
 * 2011 – The Wedding of Prince William and Catherine Middleton takes place at Westminster Abbey in London.
 * 2013 – A powerful explosion occurs in an office building in Prague, believed to have been caused by natural gas, and injures 43 people.
 * 2013  – National Airlines Flight 102, a Boeing 747-400 freighter aircraft, crashes during takeoff from Bagram Airfield in Parwan Province, Afghanistan, killing all seven people on board.
 * 2015 – A baseball game between the Baltimore Orioles and the Chicago White Sox sets the all-time low attendance mark for Major League Baseball. Zero fans were in attendance for the game, as the stadium was officially closed to the public due to the 2015 Baltimore protests.

Pre-1600

 * 1469 – William II, Landgrave of Hesse (d. 1509)
 * 1587 – Sophie of Saxony, Duchess of Pomerania (d. 1635)

1601–1900

 * 1636 – Esaias Reusner, German lute player and composer (d. 1679)
 * 1665 – James Butler, 2nd Duke of Ormonde, Irish general and politician, Lord Lieutenant of Ireland (d. 1745)
 * 1667 – John Arbuthnot, Scottish-English physician and polymath (d. 1735)
 * 1727 – Jean-Georges Noverre, French actor and dancer (d. 1810)
 * 1745 – Oliver Ellsworth, American lawyer and politician, 3rd Chief Justice of the United States (d. 1807)
 * 1758 – Georg Carl von Döbeln, Swedish general (d. 1820)
 * 1762 – Jean-Baptiste Jourdan, French general and politician, French Minister of Foreign Affairs (d. 1833)
 * 1780 – Charles Nodier, French librarian and author (d. 1844)
 * 1783 – David Cox, English landscape painter (d. 1859)
 * 1784 – Samuel Turell Armstrong, American publisher and politician, 14th Lieutenant Governor of Massachusetts (d. 1850)
 * 1810 – Thomas Adolphus Trollope, English journalist and author (d. 1892)
 * 1818 – Alexander II of Russia (d. 1881)
 * 1837 – Georges Ernest Boulanger, French general and politician, French Minister of War (d. 1891)
 * 1842 – Carl Millöcker, Austrian composer and conductor (d. 1899)
 * 1847 – Joachim Andersen, Danish flautist, composer and conductor (d. 1907)
 * 1848 – Raja Ravi Varma, Indian painter and academic (d. 1906)
 * 1854 – Henri Poincaré, French mathematician, physicist and engineer (d. 1912)
 * 1863 – Constantine P. Cavafy, Egyptian-Greek journalist and poet (d. 1933)
 * 1863  – William Randolph Hearst, American publisher and politician, founded the Hearst Corporation (d. 1951)
 * 1863  – Maria Teresia Ledóchowska, Austrian nun and missionary (d. 1922)
 * 1872 – Harry Payne Whitney, American businessman and lawyer (d. 1930)
 * 1872  – Forest Ray Moulton, American astronomer and academic (d. 1952)
 * 1875 – Rafael Sabatini, Italian-English novelist and short story writer (d. 1950)
 * 1879 – Thomas Beecham, English conductor (d. 1961)
 * 1880 – Adolf Chybiński, Polish historian, musicologist and academic (d. 1952)
 * 1882 – Auguste Herbin, French painter (d. 1960)
 * 1882  – Hendrik Nicolaas Werkman, Dutch printer, typographer, and Nazi resister (d. 1945)
 * 1885 – Egon Erwin Kisch, Czech journalist and author (d. 1948)
 * 1887 – Robert Cushman Murphy, American ornithologist (d. 1973)
 * 1888 – Michael Heidelberger, American immunologist (d. 1991)
 * 1891 – Edward Wilfred Taylor, British businessman (d. 1980)
 * 1893 – Harold Urey, American chemist and astronomer, Nobel Prize laureate (d. 1981)
 * 1894 – Marietta Blau, Austrian physicist and academic (d. 1970)
 * 1895 – Vladimir Propp, Russian scholar and critic (d. 1970)
 * 1895  – Malcolm Sargent, English organist, composer and conductor (d. 1967)
 * 1898 – E. J. Bowen, British physical chemist (d. 1980)
 * 1899 – Duke Ellington, American pianist, composer and bandleader (d. 1974)
 * 1899  – Mary Petty, American illustrator (d. 1976)
 * 1900 – Amelia Best, Australian politician (d. 1979)

1901–present

 * 1901 – Hirohito, Japanese emperor (d. 1989)
 * 1907 – Fred Zinnemann, Austrian-American director and producer (d. 1997)
 * 1908 – Jack Williamson, American author and academic (d. 2006)
 * 1909 – Tom Ewell, American actor (d. 1994)
 * 1912 – Richard Carlson, American actor, director, and screenwriter (d. 1977)
 * 1915 – Henry H. Barschall, German-American physicist and academic (d. 1997)
 * 1917 – Maya Deren, Ukrainian-American director, poet, and photographer (d. 1961)
 * 1917  – Celeste Holm, American actress and singer (d. 2012)
 * 1918 – George Allen, American football player and coach (d. 1990)
 * 1919 – Gérard Oury, French actor, director and screenwriter (d. 2006)
 * 1920 – Edward Blishen, English author and radio host (d. 1996)
 * 1920  – Harold Shapero, American composer (d. 2013)
 * 1922 – Parren Mitchell, American politician (d. 2007)
 * 1922  – Toots Thielemans, Belgian guitarist and harmonica player (d. 2016)
 * 1923 – Irvin Kershner, American actor, director and producer (d. 2010)
 * 1924 – Zizi Jeanmaire, French ballerina and actress (d. 2020)
 * 1925 – John Compton, Saint Lucian lawyer and politician, 1st Prime Minister of Saint Lucia (d. 2007)
 * 1925  – Iwao Takamoto, American animator, director, and producer (d. 2007)
 * 1926 – Elmer Kelton, American journalist and author (d. 2009)
 * 1927 – Dorothy Manley, English sprinter (d. 2021)
 * 1927  – Bill Slater, English footballer (d. 2018)
 * 1928 – Carl Gardner, American singer (d. 2011)
 * 1928  – Heinz Wolff, German-English physiologist, engineer, and academic (d. 2017)
 * 1929 – Walter Kempowski, German author and academic (d. 2007)
 * 1929  – Peter Sculthorpe, Australian composer and conductor (d. 2014)
 * 1929  – April Stevens, American singer (d. 2023)
 * 1929  – Maurice Strong, Canadian businessman and diplomat (d. 2015)
 * 1929  – Jeremy Thorpe, English lawyer and politician (d. 2014)
 * 1930 – Jean Rochefort, French actor and director (d. 2017)
 * 1931 – Frank Auerbach, British-German painter
 * 1931  – Lonnie Donegan, Scottish-English singer-songwriter and guitarist (d. 2002)
 * 1931  – Chris Pearson, Canadian politician, 1st Premier of Yukon (d. 2014)
 * 1932 – David Tindle, English painter and educator
 * 1932  – Dmitry Zaikin, Soviet pilot and cosmonaut instructor (d. 2013)
 * 1933 – Ed Charles, American baseball player and coach (d. 2018)
 * 1933  – Rod McKuen, American singer-songwriter and poet (d. 2015)
 * 1933  – Willie Nelson, American singer-songwriter, guitarist, producer and actor
 * 1934 – Luis Aparicio, Venezuelan-American baseball player
 * 1934  – Pedro Pires, Cape Verdean politician, 3rd President of Cape Verde
 * 1935 – Otis Rush, American blues singer-songwriter and guitarist (d. 2018)
 * 1936 – Zubin Mehta, Indian conductor
 * 1936  – Adolfo Nicolás, Spanish priest, 13th Superior General of the Society of Jesus (d. 2020)
 * 1936  – Alejandra Pizarnik, Argentine poet (d. 1972)
 * 1936  – Jacob Rothschild, 4th Baron Rothschild, English banker and philanthropist (d. 2024)
 * 1937 – Jill Paton Walsh, English author (d. 2020)
 * 1938 – Steven Bach, American writer, businessman and educator (d. 2009)
 * 1938  – Bernie Madoff, American businessman, financier and convicted felon (d. 2021)
 * 1939 – Klaus Rinke, German contemporary artist
 * 1940 – George Adams, American musician (d. 1992)
 * 1940  – Peter Diamond, American economist
 * 1941 – Hanne Darboven, German painter (d. 2009)
 * 1942 – Dick Chrysler, American politician
 * 1942  – Rennie Fritchie, Baroness Fritchie, English civil servant and academic
 * 1943 – Duane Allen, American country singer
 * 1943  – Brenda Dean, Baroness Dean of Thornton-le-Fylde, English union leader and politician (d. 2018)
 * 1943  – Ruth Deech, Baroness Deech, English lawyer and academic
 * 1944 – Francis Lee, English footballer and businessman (d. 2023)
 * 1945 – Hugh Hopper, English bass guitarist (d. 2009)
 * 1945  – Catherine Lara, French singer-songwriter and violinist
 * 1945  – Tammi Terrell, American soul singer-songwriter (d. 1970)
 * 1946 – Rodney Frelinghuysen, American politician and lobbyist
 * 1947 – Tommy James, American singer-songwriter, guitarist and producer
 * 1947  – Johnny Miller, American golfer and sportscaster
 * 1947  – Jim Ryun, American runner and politician
 * 1948 – Edith Brown Clement, American judge
 * 1950 – Paul Holmes, New Zealand journalist (d. 2013)
 * 1950  – Phillip Noyce, Australian director and producer
 * 1950  – Debbie Stabenow, American social worker and politician
 * 1951 – Dale Earnhardt, American race car driver (d. 2001)
 * 1951  – Jon Stanhope, Australian politician
 * 1952 – Geraldine Doogue, Australian journalist and television host
 * 1952  – Nora Dunn, American actress and comedian
 * 1952  – Bob McClure, American baseball player and coach
 * 1952  – Dave Valentin, American flautist (d. 2017)
 * 1953 – Bill Drummond, British musician
 * 1954 – Mo Brooks, American attorney and politician
 * 1954  – Jerry Seinfeld, American comedian, actor and producer
 * 1955 – Leslie Jordan, American actor, comedian, writer and singer (d. 2022)
 * 1955  – Kate Mulgrew, American actress
 * 1957 – Daniel Day-Lewis, British actor
 * 1957  – Fiamē Naomi Mataʻafa, Samoan politician, 7th Prime Minister of Samoa
 * 1957  – Joseph Morelle, American politician
 * 1958 – Kevin Moore, English footballer (d. 2013)
 * 1958  – Michelle Pfeiffer, American actress
 * 1958  – Eve Plumb, American actress
 * 1960 – Robert J. Sawyer, Canadian author and academic
 * 1962 – Polly Samson, English novelist, lyricist and journalist
 * 1963 – Mike Babcock, Canadian ice hockey player and coach
 * 1964 – Federico Castelluccio, Italian-American actor, director, producer and screenwriter
 * 1965 – Michel Bussi, French geographer, author, and academic
 * 1965  – Amy Krouse Rosenthal, American author (d. 2017)
 * 1966 – Christian Tetzlaff, German violinist
 * 1968 – Kolinda Grabar-Kitarović, Croatian politician and diplomat, 4th President of Croatia
 * 1969 – Paul Adelstein, American actor and writer
 * 1970 – Andre Agassi, American tennis player
 * 1970  – Uma Thurman, American actress
 * 1975 – Garrison Starr, American singer-songwriter and producer
 * 1975  – April Telek, Canadian actress
 * 1976 – Micol Ostow, American author, editor and educator
 * 1976  – God Shammgod, American basketball player and coach
 * 1977 – Zuzana Hejdová, Czech tennis player
 * 1977  – Claus Jensen, Danish international footballer and manager
 * 1977  – David Sullivan, American film and television actor
 * 1978 – Bob Bryan, American tennis player
 * 1978  – Mike Bryan, American tennis player
 * 1978  – Javier Colon, American singer-songwriter and musician
 * 1978  – Tyler Labine, Canadian actor and comedian
 * 1979 – Lee Dong-gook, South Korean footballer
 * 1979  – Jo O'Meara, English pop singer
 * 1980 – Mathieu Biron, Canadian ice hockey player
 * 1980  – Bre Blair, Canadian actress
 * 1981 – George McCartney, Northern Irish footballer
 * 1983 – Megan Boone, American actress
 * 1983  – Jay Cutler, American football player
 * 1983  – Sam Jones III, American actor
 * 1984 – Kirby Cote, Canadian swimmer
 * 1984  – Lina Krasnoroutskaya, Russian tennis player
 * 1986 – Byun Yo-han, South Korean actor
 * 1986  – Lee Chae-young, South Korean actress
 * 1987 – Rob Atkinson, English footballer
 * 1987  – Sara Errani, Italian tennis player
 * 1987  – Andre Russell, Jamaican cricketer
 * 1988 – Alfred Hui, Hong Kong singer
 * 1988  – Taoufik Makhloufi, Algerian athlete
 * 1988  – Jonathan Toews, Canadian ice hockey player
 * 1988  – Younha, South Korean singer-songwriter and record producer
 * 1989 – Candace Owens, American political commentator and activist
 * 1990 – James Faulkner, Australian cricketer
 * 1990  – Chris Johnson, American basketball player
 * 1991 – Adam Smith, English footballer
 * 1991  – Jung Hye-sung, South Korean actress
 * 1991  – Misaki Doi, Japanese tennis player
 * 1992 – Alina Rosenberg, German paralympic equestrian
 * 1994 – Christina Shakovets, German tennis player
 * 1996 – Katherine Langford, Australian actress
 * 1998 – Kimberly Birrell, Australian tennis player
 * 1998  – Mallory Pugh, American soccer player
 * 2002 – Sinja Kraus, Austrian tennis player
 * 2007 – Infanta Sofía of Spain, Spanish princess

Pre-1600

 * 1109 – Hugh of Cluny, French abbot (b. 1024)
 * 1380 – Catherine of Siena, Italian mystic, philosopher and saint (b. 1347)
 * 1594 – Thomas Cooper, English bishop, lexicographer, and theologian (b. 1517)

1601–1900

 * 1630 – Agrippa d'Aubigné, French soldier and poet (b. 1552)
 * 1658 – John Cleveland, English poet and author (b. 1613)
 * 1676 – Michiel de Ruyter, Dutch admiral (b. 1607)
 * 1707 – George Farquhar, Irish-English actor and playwright (b. 1678)
 * 1768 – Georg Brandt, Swedish chemist and mineralogist (b. 1694)
 * 1776 – Edward Wortley Montagu, English explorer and author (b. 1713)
 * 1833 – William Babington, Anglo-Irish physician and mineralogist (b. 1756)
 * 1848 – Chester Ashley, American politician (b. 1790)
 * 1854 – Henry Paget, 1st Marquess of Anglesey, English field marshal and politician, Lord Lieutenant of Ireland (b. 1768)

1901–present

 * 1903 – Godfrey Carter, Australian businessman and politician, 39th Mayor of Melbourne (b. 1830)
 * 1903  – Paul Du Chaillu, French-American anthropologist and zoologist (b. 1835)
 * 1905 – Ignacio Cervantes, Cuban pianist and composer (b. 1847)
 * 1916 – Jørgen Pedersen Gram, Danish mathematician and academic (b. 1850)
 * 1917 – Florence Farr, British actress, composer and director (b. 1860)
 * 1922 – Richard Croker, Irish American political boss (b. 1843)
 * 1924 – Ernest Fox Nichols, American educator and physicist (b. 1869)
 * 1925 – Ralph Delahaye Paine, American journalist and author (b. 1871)
 * 1933 – Clay Stone Briggs, American politician (b. 1876)
 * 1933  – Constantine P. Cavafy, Greek poet and journalist (b. 1863)
 * 1935 – Leroy Carr, American singer, songwriter and pianist (b. 1905)
 * 1937 – William Gillette, American actor and playwright (b. 1853)
 * 1943 – Joseph Achron, Russian composer and violinist (b. 1886)
 * 1943  – Ricardo Viñes, Spanish pianist (b. 1875)
 * 1944 – Billy Bitzer, American cinematographer (b. 1872)
 * 1944  – Pyotr Stolyarsky, Soviet violinist (b. 1871)
 * 1947 – Irving Fisher, American economist and statistician (b. 1867)
 * 1951 – Ludwig Wittgenstein, Austrian-English philosopher and academic (b. 1889)
 * 1956  – Wilhelm Ritter von Leeb, German field marshal (b. 1876)
 * 1959 – Kenneth Anderson, English soldier and Governor of Gibraltar (b. 1891)
 * 1966 – William Eccles, English physicist and engineer (b. 1875)
 * 1966  – Paula Strasberg, American actress and acting coach (b. 1909)
 * 1967 – J. B. Lenoir, American singer-songwriter and guitarist (b. 1929)
 * 1968 – Aasa Helgesen, Norwegian midwife (b. 1877)
 * 1968  – Lin Zhao, Chinese dissident (b. 1932)
 * 1978 – Theo Helfrich, German race car driver (b. 1913)
 * 1979 – Muhsin Ertuğrul, Turkish actor and director (b. 1892)
 * 1979  – Hardie Gramatky, American author and illustrator (b. 1907)
 * 1980 – Alfred Hitchcock, English-American director and producer (b. 1899)
 * 1982 – Raymond Bussières, French actor, producer and screenwriter (b. 1907)
 * 1992 – Mae Clarke, American actress (b. 1910)
 * 1993 – Michael Gordon, American actor and director (b. 1909)
 * 1993  – Mick Ronson, English guitarist, songwriter and producer (b. 1946)
 * 1997 – Mike Royko, American journalist and author (b. 1932)
 * 2000 – Phạm Văn Đồng, Vietnamese lieutenant and politician, 2nd Prime Minister of Vietnam (b. 1906)
 * 2001 – Arthur B. C. Walker Jr., American physicist and academic (b. 1936)
 * 2002 – Bob Akin, American race car driver and journalist (b. 1936)
 * 2003 – Janko Bobetko, Croatian Army general and Chief of the General Staff (b. 1919)
 * 2004 – John Henniker-Major, British diplomat and civil servant (b. 1916)
 * 2005 – William J. Bell, American screenwriter and producer (b. 1927)
 * 2005  – Louis Leithold, American mathematician and academic (b. 1924)
 * 2006 – John Kenneth Galbraith, Canadian-American economist and diplomat, United States Ambassador to India (b. 1908)
 * 2007 – Josh Hancock, American baseball player (b. 1978)
 * 2007  – Dick Motz, New Zealand cricketer and rugby player (b. 1940)
 * 2007  – Ivica Račan, Croatian politician, 7th Prime Minister of Croatia (b. 1944)
 * 2008 – Gordon Bradley, English-American footballer (b. 1933)
 * 2008  – Albert Hofmann, Swiss chemist and academic (b. 1906)
 * 2010 – Avigdor Arikha, French-Israeli artist, printmaker and art historian (b. 1929)
 * 2011 – Siamak Pourzand, Iranian journalist and critic (b. 1931)
 * 2011  – Joanna Russ, American writer, academic and radical feminist (b. 1937)
 * 2012 – Shukri Ghanem, Libyan politician, 22nd Prime Minister of Libya (b. 1942)
 * 2012  – Joel Goldsmith, American composer and conductor (b. 1957)
 * 2012  – Roland Moreno. French engineer, invented the smart card (b. 1945)
 * 2012  – Kenny Roberts, American singer-songwriter (b. 1926)
 * 2013 – Alex Elisala, New Zealand-Australian rugby player (b. 1992)
 * 2013  – Pesah Grupper, Israeli politician, 13th Israel Minister of Agriculture (b. 1924)
 * 2013  – John La Montaine, American pianist and composer (b. 1920)
 * 2013  – Kevin Moore, English footballer (b. 1958)
 * 2013  – Marianna Zachariadi, Greek pole vaulter (b. 1990)
 * 2014 – Iveta Bartošová, Czech singer and actress (b. 1966)
 * 2014  – Al Feldstein, American author and illustrator (b. 1925)
 * 2014  – Bob Hoskins, English actor (b. 1942)
 * 2015 – François Michelin, French businessman (b. 1926)
 * 2015  – Jean Nidetch, American businesswoman, co-founded Weight Watchers (b. 1923)
 * 2015  – Calvin Peete, American golfer (b. 1943)
 * 2015  – Dan Walker, American lawyer and politician, 36th Governor of Illinois (b. 1922)
 * 2016 – Renato Corona, Filipino lawyer and jurist, 23rd Chief Justice of the Supreme Court of the Philippines (b. 1948)
 * 2017 – R. Vidyasagar Rao, Indian bureaucrat and activist (b. 1939)
 * 2018 – Luis García Meza, Bolivian general, 57th President of Bolivia (b. 1929)
 * 2018  – Michael Martin, British politician (b. 1945)
 * 2019 – Josef Šural, Czech footballer (b. 1990)
 * 2020 – Irrfan Khan, Indian actor (b. 1967)
 * 2020  – Guido Münch, Mexican astronomer and astrophysicist (b. 1921)
 * 2021 – Cate Haste, English author (b. 1945)
 * 2022 – Joanna Barnes, American actress and writer (b. 1934)
 * 2023 – Padma Desai, Indian-American development economist (b. 1931)

Holidays and observances

 * Christian feast day:
 * Catherine of Siena (Catholic, Lutheran and Anglican Church)
 * Hugh of Cluny
 * Robert of Molesme
 * Wilfrid II
 * April 29 (Eastern Orthodox liturgics)
 * Day of Remembrance for all Victims of Chemical Warfare (United Nations)
 * International Dance Day (UNESCO)
 * Shōwa Day, traditionally the start of the Golden Week holiday period, which is April 29 and May 3–5. (Japan)

title: April 29


text:
August 14

Pre-1600

 * 74 BC – A group of officials, led by the Western Han minister Huo Guang, present articles of impeachment against the new emperor, Liu He, to the imperial regent, Empress Dowager Shangguan.
 * 29 BC – Octavian holds the second of three consecutive triumphs in Rome to celebrate the victory over the Dalmatian tribes.
 * 1040 – King Duncan I is killed in battle against his first cousin and rival Macbeth. The latter succeeds him as King of Scotland.
 * 1183 – Taira no Munemori and the Taira clan take the young Emperor Antoku and the three sacred treasures and flee to western Japan to escape pursuit by the Minamoto clan.
 * 1264 – After tricking the Venetian galley fleet into sailing east to the Levant, the Genoese capture an entire Venetian trade convoy at the Battle of Saseno.
 * 1352 – War of the Breton Succession: Anglo-Bretons defeat the French in the Battle of Mauron.
 * 1370 – Charles IV, Holy Roman Emperor, grants city privileges to Karlovy Vary.
 * 1385 – Portuguese Crisis of 1383–85: Battle of Aljubarrota: Portuguese forces commanded by John I of Portugal defeat the Castilian army of John I of Castile.
 * 1592 – The first sighting of the Falkland Islands by John Davis.
 * 1598 – Nine Years' War: Battle of the Yellow Ford: Irish forces under Hugh O'Neill, Earl of Tyrone, defeat an English expeditionary force under Henry Bagenal.

1601–1900

 * 1720 – The Spanish military Villasur expedition is defeated by Pawnee and Otoe warriors near present-day Columbus, Nebraska.
 * 1784 – Russian colonization of North America: Awa’uq Massacre: The Russian fur trader Grigory Shelikhov storms a Kodiak Island Alutiit refuge rock on Sitkalidak Island, killing 500+ Alutiit.
 * 1790 – The Treaty of Wereloe ended the 1788–1790 Russo-Swedish War.
 * 1791 – Slaves from plantations in Saint-Domingue hold a Vodou ceremony led by houngan Dutty Boukman at Bois Caïman, marking the start of the Haitian Revolution.
 * 1814 – A cease fire agreement, called the Convention of Moss, ended the Swedish–Norwegian War.
 * 1816 – The United Kingdom formally annexes the Tristan da Cunha archipelago, administering the islands from the Cape Colony in South Africa.
 * 1842 – American Indian Wars: Second Seminole War ends, with the Seminoles forced from Florida.
 * 1848 – Oregon Territory is organized by act of Congress.
 * 1880 – Construction of Cologne Cathedral, the most famous landmark in Cologne, Germany, is completed.
 * 1885 – Japan's first patent is issued to the inventor of a rust-proof paint.
 * 1893 – France becomes the first country to introduce motor vehicle registration.
 * 1900 – Battle of Peking: The Eight-Nation Alliance occupies Beijing, China, in a campaign to end the bloody Boxer Rebellion in China.

1901–present

 * 1901 – The first claimed powered flight, by Gustave Whitehead in his Number 21.
 * 1914 – World War I: Start of the Battle of Lorraine, an unsuccessful French offensive.
 * 1917 – World War I: The Republic of China, which had heretofore been shipping labourers to Europe to assist in the war effort, officially declares war on the Central Powers, although it will continue to send to Europe labourers instead of combatants for the remaining duration of the war.
 * 1920 – The 1920 Summer Olympics, having started four months earlier, officially open in Antwerp, Belgium, with the newly-adopted Olympic flag and the Olympic oath being raised and taken at the Opening Ceremony for the first time in Olympic history.
 * 1921 – Tannu Uriankhai, later Tuvan People's Republic is established as a completely independent country (which is supported by Soviet Russia).
 * 1933 – Loggers cause a forest fire in the Coast Range of Oregon, later known as the first forest fire of the Tillamook Burn; destroying 240,000 acre of land.
 * 1935 – Franklin D. Roosevelt signs the Social Security Act, creating a government pension system for the retired.
 * 1936 – Rainey Bethea is hanged in Owensboro, Kentucky in the last known public execution in the United States.
 * 1941 – World War II: Winston Churchill and Franklin D. Roosevelt sign the Atlantic Charter of war stating postwar aims.
 * 1947 – Pakistan gains independence from the British Empire.
 * 1948 – Beaver drop a Idaho Department of Fish and Game program to relocate beavers from Northwestern Idaho to the Chamberlain Basin in Central Idaho. The program involved parachuting beavers into the Chamberlain Basin.
 * 1959 – Founding and first official meeting of the American Football League.
 * 1967 – UK Marine Broadcasting Offences Act 1967 declares participation in offshore pirate radio illegal.
 * 1969 – The Troubles: British troops are deployed in Northern Ireland as political and sectarian violence breaks out, marking the start of the 37-year Operation Banner.
 * 1971 – Bahrain declares independence from Britain.
 * 1972 – An Ilyushin Il-62 airliner crashes near Königs Wusterhausen, East Germany killing 156 people.
 * 1980 – Lech Wałęsa leads strikes at the Gdańsk, Poland shipyards.
 * 1994 – Ilich Ramírez Sánchez, also known as "Carlos the Jackal", is captured.
 * 1996 – Greek Cypriot refugee Solomos Solomou is shot and killed by a Turkish security officer while trying to climb a flagpole in order to remove a Turkish flag from its mast in the United Nations Buffer Zone in Cyprus.
 * 2003 – A widescale power blackout affects the northeast United States and Canada.
 * 2005 – Helios Airways Flight 522, en route from Larnaca, Cyprus to Prague, Czech Republic via Athens, crashes in the hills near Grammatiko, Greece, killing 121 passengers and crew.
 * 2006 – Lebanon War: A ceasefire takes effect three days after the United Nations Security Council’s approval of United Nations Security Council Resolution 1701, formally ending hostilities between Lebanon and Israel.
 * 2006 – Sri Lankan Civil War: Sixty-one schoolgirls killed in Chencholai bombing by Sri Lankan Air Force air strike.
 * 2007 – The Kahtaniya bombings kills at least 500 people.
 * 2013 – Egypt declares a state of emergency as security forces kill hundreds of demonstrators supporting former president Mohamed Morsi.
 * 2013  – UPS Airlines Flight 1354 crashes short of the runway at Birmingham–Shuttlesworth International Airport, killing both crew members on board.
 * 2015 – The U.S. Embassy in Havana, Cuba re-opens after 54 years of being closed when Cuba–United States relations were broken off.
 * 2021 – A magnitude 7.2 earthquake strikes southwestern Haiti, killing at least 2,248 people and causing a humanitarian crisis.
 * 2022 – An explosion destroys a market in Armenia, killing six people and injuring dozens.
 * 2023 – Former U.S. President Donald Trump is charged in Georgia along with 18 others in attempting to overturn the results of the 2020 election in that state, his fourth indictment of 2023.

Pre-1600

 * 1479 – Catherine of York (d. 1527)
 * 1499 – John de Vere, 14th Earl of Oxford, English politician (d. 1526)
 * 1502 – Pieter Coecke van Aelst, Flemish painter (d. 1550)
 * 1530 – Giambattista Benedetti, Italian mathematician and physicist (d. 1590)
 * 1552 – Paolo Sarpi, Italian writer (d. 1623)
 * 1599 – Méric Casaubon, Swiss-English scholar and author (d. 1671)

1601–1900

 * 1642 – Cosimo III de' Medici, Grand Duke of Tuscany (d. 1723)
 * 1653 – Christopher Monck, 2nd Duke of Albemarle, English colonel and politician, Lieutenant Governor of Jamaica (d. 1688)
 * 1688 – Frederick William I of Prussia (d. 1740)
 * 1714 – Claude Joseph Vernet, French painter (d. 1789)
 * 1738 – Leopold Hofmann, Austrian composer and conductor (d. 1793)
 * 1742 – Pope Pius VII (d. 1823)
 * 1758 – Carle Vernet, French painter and lithographer (d. 1836)
 * 1777 – Hans Christian Ørsted, Danish physicist and chemist (d. 1851)
 * 1802 – Letitia Elizabeth Landon, English poet and novelist (d. 1838)
 * 1814 – Charlotte Fowler Wells, American phrenologist and publisher (d. 1901)
 * 1817 – Alexander H. Bailey, American lawyer, judge, and politician (d. 1874)
 * 1840 – Richard von Krafft-Ebing, German-Austrian psychologist and author (d. 1902)
 * 1847 – Robert Comtesse, Swiss lawyer and politician (d. 1922)
 * 1848 – Margaret Lindsay Huggins, Anglo-Irish astronomer and author (d. 1915)
 * 1851 – Doc Holliday, American dentist and gambler (d. 1887)
 * 1860 – Ernest Thompson Seton, American author, artist, and naturalist (d. 1946)
 * 1863 – Ernest Thayer, American poet and author (d. 1940)
 * 1865 – Guido Castelnuovo, Italian mathematician and academic (d. 1952)
 * 1866 – Charles Jean de la Vallée-Poussin, Belgian mathematician and academic (d. 1962)
 * 1867 – Cupid Childs, American baseball player (d. 1912)
 * 1867  – John Galsworthy,  English novelist and playwright, Nobel Prize laureate (d. 1933)
 * 1871 – Guangxu Emperor of China (d. 1908)
 * 1875 – Mstislav Dobuzhinsky, Russian-Lithuanian painter and illustrator (d. 1957)
 * 1876 – Alexander I of Serbia (d. 1903)
 * 1881 – Francis Ford, American actor, director, producer, and screenwriter (d. 1953)
 * 1883 – Ernest Everett Just, American biologist and academic (d. 1941)
 * 1886 – Arthur Jeffrey Dempster, Canadian-American physicist and academic (d. 1950)
 * 1889 – Otto Tief, Estonian lawyer and politician, Prime Minister of Estonia (d. 1976)
 * 1890 – Bruno Tesch, German chemist and businessman (d. 1946)
 * 1892 – Kaikhosru Shapurji Sorabji, English pianist, composer, and critic (d. 1988)
 * 1894 – Frank Burge, Australian rugby league player and coach (d. 1958)
 * 1895 – Jack Gregory, Australian cricketer (d. 1973)
 * 1895  – Amaza Lee Meredith, American architect (d. 1984)
 * 1896 – Albert Ball, English fighter pilot (d. 1917)
 * 1896  – Theodor Luts, Estonian director and cinematographer (d. 1980)
 * 1900 – Margret Boveri, German journalist (d. 1975)

1901–present

 * 1910 – Nüzhet Gökdoğan, Turkish astronomer and mathematician (d. 2003)
 * 1910  – Willy Ronis, French photographer (d. 2009)
 * 1910  – Pierre Schaeffer, French composer and producer (d. 1995)
 * 1912 – Frank Oppenheimer, American physicist and academic (d. 1985)
 * 1913 – Hector Crawford, Australian director and producer (d. 1991)
 * 1913  – Paul Dean, American baseball player (d. 1981)
 * 1914 – Herman Branson, American physicist, chemist, and academic (d. 1995)
 * 1915 – B. A. Santamaria, Australian political activist and publisher (d. 1998)
 * 1916 – Frank and John Craighead, American naturalists (twins, Frank d. 2001, John d. 2016)
 * 1916  – Wellington Mara, American businessman (d. 2005)
 * 1923 – Alice Ghostley, American actress (d. 2007)
 * 1924 – Sverre Fehn, Norwegian architect, designed the Hedmark Museum (d. 2009)
 * 1924  – Georges Prêtre, French conductor (d. 2017)
 * 1925 – Russell Baker, American critic and essayist (d. 2019)
 * 1926 – René Goscinny, French author and illustrator (d. 1977)
 * 1926  – Buddy Greco, American singer and pianist (d. 2017)
 * 1928 – Lina Wertmüller, Italian director and screenwriter (d. 2021)
 * 1929 – Giacomo Capuzzi, Italian Roman Catholic prelate, bishop of the Roman Catholic Diocese of Lodi from 1989 to 2005 (d. 2021).
 * 1929  – Dick Tiger, Nigerian boxer (d. 1971)
 * 1930 – Arthur Latham, British politician and Member of Parliament (d. 2016)
 * 1930  – Earl Weaver, American baseball player and manager (d. 2013)
 * 1931 – Frederic Raphael, American journalist, author, and screenwriter
 * 1932 – Lee Hoffman, American author (d. 2007)
 * 1933 – Richard R. Ernst, Swiss chemist and academic, Nobel Prize laureate (d. 2021)
 * 1935 – John Brodie, American football player
 * 1938 – Bennie Muller, Dutch footballer (d. 2024)
 * 1941 – David Crosby, American singer-songwriter and guitarist (d. 2023)
 * 1941  – Connie Smith, American country music singer-songwriter and guitarist
 * 1942 – Willie Dunn, Canadian singer-songwriter and producer (d. 2013)
 * 1943 – Ronnie Campbell, English miner and politician (d. 2024)
 * 1943  – Ben Sidran, American jazz and rock keyboardist
 * 1945 – Steve Martin, American actor, comedian, musician, producer, and screenwriter
 * 1945  – Wim Wenders, German director, producer, and screenwriter
 * 1946 – Antonio Fargas, American actor
 * 1946  – Larry Graham, American soul/funk bass player and singer-songwriter
 * 1946  – Susan Saint James, American actress
 * 1946  – Tom Walkinshaw, Scottish race car driver and businessman (d. 2010)
 * 1947 – Maddy Prior, English folk singer
 * 1947  – Danielle Steel, American author
 * 1947  – Joop van Daele, Dutch footballer
 * 1949 – Bob Backlund, American wrestler
 * 1949  – Morten Olsen, Danish footballer
 * 1950 – Gary Larson, American cartoonist
 * 1951 – Slim Dunlap, American singer-songwriter and guitarist
 * 1951  – Carl Lumbly, American actor
 * 1952 – Debbie Meyer, American swimmer
 * 1953 – James Horner, American composer and conductor (d. 2015)
 * 1954 – Mark Fidrych, American baseball player and sportscaster (d. 2009)
 * 1954  – Stanley A. McChrystal, American general
 * 1956 – Jackée Harry, American actress and television personality
 * 1956  – Andy King, English footballer and manager (d. 2015)
 * 1956  – Rusty Wallace, American race car driver
 * 1957 – Peter Costello, Australian lawyer and politician
 * 1959 – Frank Brickowski, American basketball player
 * 1959  – Marcia Gay Harden, American actress
 * 1959  – Magic Johnson, American basketball player and coach
 * 1960 – Sarah Brightman, English singer and actress
 * 1960  – Fred Roberts, American basketball player
 * 1961 – Susan Olsen, American actress and radio host
 * 1962 – Mark Gubicza, American baseball player
 * 1963 – José Cóceres, Argentinian golfer
 * 1964 – Neal Anderson, American football player and coach
 * 1964  – Jason Dunstall, Australian footballer
 * 1965 – Paul Broadhurst, English golfer
 * 1966 – Halle Berry, American model, actress, and producer
 * 1966  – Karl Petter Løken, Swedish-Norwegian footballer
 * 1968 – Ben Bass, American actor
 * 1968  – Catherine Bell, English-American actress and producer
 * 1968  – Darren Clarke, Northern Irish golfer
 * 1968  – Jason Leonard, English rugby player
 * 1969 – Tracy Caldwell Dyson, American chemist and astronaut
 * 1969  – Stig Tøfting, Danish footballer
 * 1970 – Kevin Cadogan, American rock guitarist
 * 1971 – Raoul Bova, Italian actor, producer, and screenwriter
 * 1971  – Benito Carbone, Italian footballer
 * 1971  – Peter Franzén, Finnish actor
 * 1971  – Mark Loretta, American baseball player
 * 1972 – Laurent Lamothe, Haitian businessman and politician, Prime Minister of Haiti
 * 1973 – Jared Borgetti, Mexican footballer
 * 1973  – Kieren Perkins, Australian swimmer
 * 1974 – Chucky Atkins, American basketball player
 * 1974  – Christopher Gorham, American actor
 * 1975 – Mike Vrabel, American football player
 * 1976 – Fabrizio Donato, Italian triple jumper
 * 1977 – Juan Pierre, American baseball player
 * 1978 – Anastasios Kyriakos, Greek footballer
 * 1978  – Greg Rawlinson, New Zealand rugby player
 * 1979 – Paul Burgess, Australian pole vaulter
 * 1980 – Peter Malinauskas, Australian politician, 47th Premier of South Australia
 * 1981 – Earl Barron, American basketball player
 * 1981  – Paul Gallen, Australian rugby league player, boxer, and sportscaster
 * 1981  – Julius Jones, American football player
 * 1981  – Kofi Kingston, Ghanaian-American wrestler
 * 1981  – Scott Lipsky, American tennis player
 * 1983 – Elena Baltacha, Ukrainian-Scottish tennis player (d. 2014)
 * 1983  – Mila Kunis, Ukrainian-American actress
 * 1983  – Lamorne Morris, American actor and comedian
 * 1983  – Spencer Pratt, American television personality
 * 1984 – Eva Birnerová, Czech tennis player
 * 1984  – Clay Buchholz, American baseball player
 * 1984  – Giorgio Chiellini, Italian footballer
 * 1984  – Josh Gorges, Canadian ice hockey player
 * 1984  – Nick Grimshaw, English radio and television host
 * 1984  – Nicola Slater, Scottish tennis player
 * 1984  – Robin Söderling, Swedish tennis player
 * 1985 – Christian Gentner, German footballer
 * 1985  – Shea Weber, Canadian ice hockey player
 * 1986 – Braian Rodríguez, Uruguayan footballer
 * 1987 – Johnny Gargano, American wrestler
 * 1987  – David Peralta, Venezuelan baseball player
 * 1987  – Tim Tebow, American football and baseball player and sportscaster
 * 1989 – Ander Herrera, Spanish footballer
 * 1989  – Kyle Turris, Canadian ice hockey player
 * 1991 – Richard Freitag, German ski jumper
 * 1991 – Giovanny Gallegos, Mexican baseball player
 * 1995 – Léolia Jeanjean, French tennis player
 * 1997 – Greet Minnen, Belgian tennis player
 * 2004 – Marsai Martin, American actress and producer

Pre-1600

 * 582 – Tiberius II Constantine, Byzantine emperor
 * 1040 – Duncan I of Scotland
 * 1167 – Rainald of Dassel, Italian archbishop
 * 1204 – Minamoto no Yoriie, second Shōgun of the Kamakura shogunate
 * 1433 – John I of Portugal (b. 1357)
 * 1464 – Pope Pius II (b. 1405)
 * 1573 – Saitō Tatsuoki, Japanese daimyō (b. 1548)

1601–1900

 * 1691 – Richard Talbot, 1st Earl of Tyrconnell, Irish soldier and politician (b. 1630)
 * 1716 – Madre María Rosa, Capuchin nun from Spain, to Peru (b. 1660)
 * 1727 – William Croft, English organist and composer (b. 1678)
 * 1774 – Johann Jakob Reiske, German physician and scholar (b. 1716)
 * 1784 – Nathaniel Hone the Elder, Irish-born English painter and academic (b. 1718)
 * 1852 – Margaret Taylor, First Lady of the United States (b. 1788)
 * 1854 – Carl Carl, Polish-born actor and theatre director (b. 1787)
 * 1860 – André Marie Constant Duméril, French zoologist and entomologist (b. 1774)
 * 1870 – David Farragut, American admiral (b. 1801)
 * 1890 – Michael J. McGivney, American priest, founded the Knights of Columbus (b. 1852)
 * 1891 – Sarah Childress Polk, First Lady of the United States (b. 1803)

1901–present

 * 1905 – Simeon Solomon, English soldier and painter (b. 1840)
 * 1909 – William Stanley, British engineer and author (b. 1829)
 * 1922 – Rebecca Cole, American physician and social reformer (b. 1846)
 * 1928 – Klabund, German author and poet (b. 1890)
 * 1938 – Hugh Trumble, Australian cricketer and accountant (b. 1876)
 * 1941 – Maximilian Kolbe, Polish martyr and saint (b. 1894)
 * 1941  – Paul Sabatier, French chemist and academic, Nobel Prize laureate (b. 1854)
 * 1943 – Joe Kelley, American baseball player and manager (b. 1871)
 * 1948 – Eliška Misáková, Czech gymnast (b. 1926)
 * 1951 – William Randolph Hearst, American publisher and politician, founded the Hearst Corporation (b. 1863)
 * 1954 – Hugo Eckener, German pilot and designer (b. 1868)
 * 1955 – Herbert Putnam, American lawyer and publisher, Librarian of Congress (b. 1861)
 * 1956 – Bertolt Brecht, German poet, playwright, and director (b. 1898)
 * 1956  – Konstantin von Neurath, German lawyer and politician, Reich Minister of Foreign Affairs (b. 1873)
 * 1958 – Frédéric Joliot-Curie, French physicist and chemist, Nobel Prize laureate (b. 1900)
 * 1963 – Clifford Odets, American director, playwright, and screenwriter (b. 1906)
 * 1964 – Johnny Burnette, American singer-songwriter (b. 1934)
 * 1965 – Vello Kaaristo, Estonian skier (b. 1911)
 * 1967 – Bob Anderson, English motorcycle racer and race car driver (b. 1931)
 * 1972 – Oscar Levant, American actor, pianist, and composer (b. 1906)
 * 1972  – Jules Romains, French author and poet (b. 1885)
 * 1973 – Fred Gipson, American journalist and author (b. 1908)
 * 1978 – Nicolas Bentley, English author and illustrator (b. 1907)
 * 1980 – Dorothy Stratten, Canadian-American model and actress (b. 1960)
 * 1981 – Karl Böhm, Austrian conductor and director (b. 1894)
 * 1981  – Dudley Nourse, South African cricketer (b. 1910)
 * 1982 – Mahasi Sayadaw, Burmese monk and philosopher (b. 1904)
 * 1984 – Spud Davis, American baseball player, coach, and manager (b. 1904)
 * 1984  – J. B. Priestley, English novelist and playwright (b. 1894)
 * 1985 – Gale Sondergaard, American actress (b. 1899)
 * 1988 – Roy Buchanan, American singer-songwriter and guitarist (b. 1939)
 * 1988  – Robert Calvert, South African-English singer-songwriter and playwright (b. 1945)
 * 1988  – Enzo Ferrari, Italian race car driver and businessman, founded Ferrari (b. 1898)
 * 1991 – Alberto Crespo, Argentinian race car driver (b. 1920)
 * 1992 – John Sirica, American lawyer and judge (b. 1904)
 * 1994 – Elias Canetti, Bulgarian-Swiss author, Nobel Prize laureate (b. 1905)
 * 1994  – Alice Childress, American actress, playwright, and author (b. 1912)
 * 1996 – Sergiu Celibidache, Romanian conductor and composer (b. 1912)
 * 1999 – Pee Wee Reese, American baseball player and sportscaster (b. 1918)
 * 2002 – Larry Rivers, American painter and sculptor (b. 1923)
 * 2003 – Helmut Rahn, German footballer (b. 1929)
 * 2004 – Czesław Miłosz, Polish-born American novelist, essayist, and poet, Nobel Prize laureate (b. 1911)
 * 2004  – Trevor Skeet, New Zealand-English lawyer and politician (b. 1918)
 * 2006 – Bruno Kirby, American actor (b. 1949)
 * 2007 – Tikhon Khrennikov, Russian pianist and composer (b. 1913)
 * 2010 – Herman Leonard, American photographer (b. 1923)
 * 2012 – Vilasrao Deshmukh, Indian lawyer and politician, Chief Minister of Maharashtra (b. 1945)
 * 2012  – Svetozar Gligorić, Serbian chess player (b. 1923)
 * 2012  – Phyllis Thaxter, American actress (b. 1919)
 * 2013 – Jack Germond, American journalist and author (b. 1928)
 * 2014 – Leonard Fein, American journalist and academic, co-founded Moment Magazine (b. 1934)
 * 2014  – George V. Hansen, American politician (b. 1930)
 * 2015 – Bob Johnston, American songwriter and producer (b. 1932)
 * 2016 – Fyvush Finkel, American actor (b. 1922)
 * 2018 – Jill Janus, American singer (b. 1975)
 * 2019 – Polly Farmer, Australian footballer and coach (b. 1935)
 * 2020 – Julian Bream, English classical guitarist and lutenist (b. 1933)
 * 2020  – Angela Buxton, British tennis player (b. 1934)
 * 2020  – James R. Thompson, American politician, Governor of Illinois (b. 1936)
 * 2021 – Michael Aung-Thwin, American historian and scholar of Burmese and Southeast Asian history (b. 1946)
 * 2023 – Delwar Hossain Sayeedi Bangladeshi Islamic lecturer, politician (b. 1940)

Holidays and observances

 * Christian feast day:
 * Arnold of Soissons
 * Domingo Ibáñez de Erquicia
 * Eusebius of Rome
 * Jonathan Myrick Daniels (Episcopal Church)
 * Maximilian Kolbe
 * National Navajo Code Talkers Day is a holiday in the United States honoring Navajo code talkers in the military.
 * Falklands Day is the celebration of the first sighting of the Falkland Islands by John Davis in 1592.
 * Independence Day celebrates the independence of Pakistan from the United Kingdom in 1947.
 * Partition Horrors Remembrance Day commemorates the victims and sufferings of people during the Partition of India in 1947.

title: August 14