Chemistry of sulfenic acids. 7. Reason for the high reactivity of sulfenic acids. Stabilization by intramolecular hydrogen bonding and electronegativity effects

FA Davis, LA Jenkins, RL Billmers

Index: Davis, Franklin A.; Jenkins, Linda A.; Billmers, Robert L. Journal of Organic Chemistry, 1986 , vol. 51, # 7 p. 1033 - 1040

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Citation Number: 94

Abstract

It is proposed that the reason sulfenic acids (RSOH) are so reactive and usually not isolated or even detected is that they form thiosulfinates (RS (0) SR) so readily. This is a consequence of the sulfenic acid hydrogen-bonded dimer, 1, which lowers the energy of activation for thiosulfinate formation. The stability of the few sulfenic acids that have been isolated can be explained in terms of steric, electronic, and intramolecular hydrogen- ...