✦ LIBER ✦

Physical properties of organic thiones: Part V. Effect of substituents with thiocarbonyl functions on acid strength

✍ Scribed by M. J. Janssen

Publisher: Elsevier Science
Year: 2010
Tongue: English
Weight: 494 KB
Volume: 82
Category: Article
ISSN: 0165-0513
DOI: 10.1002/recl.19630820911

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✦ Synopsis

Abstract

The acid dissociation constants of a number of substituted acetic acids were determined. Compounds were of the general type AC = X—BCH~2~COOH with A methyl, alkoxy, alkylthio or dimethylamino, X oxygen or sulphur, B oxygen, sulphur or nitrogen. The influence of the substituent AC(X)B upon the acidity is related to electronic (mesomeric and inductive) effects. In one instance complication by steric effects arises. The main results support the model, previously conceived for thiones with heteroatoms attached to the thiocarbonyl group: extensive mesomeric electron displacements together with appreciable contributions from inductive shifts, the latter especially noteworthy, where sulphur is concerned. In the molecules studied the thiocarbonyl group is more electron‐attracting than the carbonyl group.

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