I am studying aromaticity, and apparently, aromaticity is common in biological molecules, just like 6-member rings (relieve ring strain and angle strain). I was wondering: is it because aromaticity makes the compound more stable to prevent unwanted reactions/modifications?

Thank you!


I finally found something interesting. Tyrosine, phenylalanine, and tryptophan interacts with cation-pi interactions in proteins to stabilize secondary structures. They are also over-represented in protein binding sites.

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    $\begingroup$ Orthogonal mechanism that comes to mind : evolution tried random molecules -> lower energy / more stable molecules were more likely to be tried -> evolution disproportionately tried aromatic molecules -> biological compounds have lots of aromaticity. $\endgroup$
    – SCH
    Dec 18, 2016 at 22:48
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    $\begingroup$ Personally I don't think this is representative of anything. Of the 20 amino acids only 4 have aromatic rings. $\endgroup$ Dec 19, 2016 at 3:46
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    $\begingroup$ Ah, well, as for why they are over-represented in binding sites, that's a different question (and pretty interesting, too). $\endgroup$ Dec 19, 2016 at 18:11
  • $\begingroup$ Pi-stacking between the aromatic nucleobases in DNA helps stabilize the double helix structure. $\endgroup$ Dec 20, 2016 at 0:53
  • $\begingroup$ Relared - chemistry.stackexchange.com/questions/60055/… $\endgroup$ Dec 24, 2016 at 4:10


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