Sulfenic acids

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Structure of 1-propensulfenic acid

Sulfenic acids are a class of chemical compounds with organically bound sulfur and oxygen with the general structure R – S – OH, where R is an alkyl or aryl radical . Their esters and salts are the sulfenates.

Stability and use

Sulfenic acids are quite unstable compounds and are of no great importance. The sulfenyl halides (R – S – Hal), the most important derivatives of sulfenic acids, are more stable. Especially sulfenyl chlorides (R-S-Cl) find versatile application in preparative chemistry.

Food preparation and origination

A well-known representative of sulfenic acids is 1-propensulfenic acid , the tear-inducing substance in onions . 1-propensulfenic acid is not contained in fresh onions, but is produced when they are cut through the enzymatic breakdown of (+) - S -propenyl- L - cysteine - S -oxide . The enzyme and the precursor are located in the intact onion in different cell compartments . Only after some cells have been destroyed does the reaction to form 1-propensulfenic acid begin.

Individual evidence

  1. Alfons Schöberl and Annemarie Wagner in: Houben-Weyl Methods of Organic Chemistry , edited by Eugen Müller, Otto Bayer, Hans Meerwein and Karl Ziegler, Volume 9, sulfur, selenium and tellurium compounds , Thieme Verlag, Stuttgart 1955, p. 263-284.
  2. ^ A b Siegfried Hauptmann : Organic Chemistry , 2nd revised edition, VEB Deutscher Verlag für Grundstoffindindustrie, Leipzig 1985, ISBN 3-342-00280-8 , pp. 480-481.
  3. ^ Brockhaus ABC Chemie in two volumes , VEB FA Brockhaus Verlag, Leipzig 1965, p. 1361.