Thiocarboxylic acid

Thione form (carbothioic O-acid)
Thiol form (carbothioic S-acid)

In organic chemistry, thiocarboxylic acids or carbothioic acids are organosulfur compounds related to carboxylic acids by replacement of one of the oxygen atoms with a sulfur atom. Two tautomers are possible: a thione form (RC(S)OH) and a thiol form (RC(O)SH).[1][2] These are sometimes also referred to as "carbothioic O-acid" and "carbothioic S-acid" respectively. Of these the thiol form is most common (e.g. thioacetic acid).

Thiocarboxylic acids are rare in nature, however the biosynthetic components for producing them appear widespread in bacteria.[3] Examples include pyridine-2,6-dicarbothioic acid,[4] and thioquinolobactin.[3]

  1. ^ Cremlyn, R.J. (1996). An introduction to organosulfur chemistry. Chichester: Wiley. ISBN 0-471-95512-4.
  2. ^ Janssen, Matthys J. (1969). "Thiolo, thiono and dithio acids and esters". In Saul Patai (ed.). Carboxylic Acids and Esters. The Chemistry of Functional Groups. New York: John Wiley. pp. 705–764. doi:10.1002/9780470771099.ch15. ISBN 978-0-470-77109-9.
  3. ^ a b Dong, Liao-Bin; Rudolf, Jeffrey D.; Kang, Dingding; Wang, Nan; He, Cyndi Qixin; Deng, Youchao; Huang, Yong; Houk, K. N.; Duan, Yanwen; Shen, Ben (2018). "Biosynthesis of thiocarboxylic acid-containing natural products". Nature Communications. 9: 2362. Bibcode:2018NatCo...9.2362D. doi:10.1038/s41467-018-04747-y. PMC 6006322. PMID 29915173.
  4. ^ Budzikiewicz, Herbert (2010). "Microbial Siderophores". In Kinghorn, A. Douglas; Falk, Heinz; Kobayashi, Junichi (eds.). Fortschritte der Chemie organischer Naturstoffe / Progress in the Chemistry of Organic Natural Products, Vol. 92 [Progress in the Chemistry of Organic Natural Products]. Vol. 92. pp. 1–75. doi:10.1007/978-3-211-99661-4_1. ISBN 978-3-211-99660-7. PMID 20198464.
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