๐”– Bobbio Scriptorium
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On the acidity of thiol esters

โœ Scribed by G.Edwin Wilson Jr.

Publisher
Elsevier Science
Year
1967
Tongue
French
Weight
232 KB
Volume
8
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Thiol eaters, important in the bioryntheeia of fatty acida, have been shown to be much more acidic than eaters(l).

In order to rationalize the large difference in acidities, Cronyn and co-workers(2) proposed that the eater anion would be greatly destabilized relative to an a-keto carbanion because of the competition between the ether oxygen atom and the carbanion to donate electrons to the carbonvl oxygen atom through the P -system. The thiol ester on the other hand would not be destabilized by a high degree of croaa conjugation and would be intermediate betweenketone and ester anionq in stability. This would obtain because of the poor TT -overlap of the 3p-orbital of sulfur with the 2p-orbital of oxygen and the consequent unimportance of the charge-separated resonance form to the thiol eater.

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