✦ LIBER ✦

Carbon acidity. 97. Cesium ion pair acidity of some sulfones in cyclohexylamine

✍ Scribed by Andrew Streitwieser; George W. Schriver

Publisher: John Wiley and Sons
Year: 1997
Tongue: English
Weight: 152 KB
Volume: 8
Category: Article
ISSN: 1042-7163
DOI: 10.1002/(sici)1098-1071(1997)8:6<533::aid-hc13>3.0.co;2-s

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✦ Synopsis

The ion pair acidities of several sulfones were measured on the cesium-cyclohexylamine scale. Cyclopropyl phenyl sulfone is less acidic than isopropyl phenyl sulfone in agreement with earlier results in dimethyl sulfoxide. The acidities of a series of substituted phenyl methyl sulfones show that the sulfone group is an effective insulator; there is no significant delocalization of carbanion charge across the sulfone group into the phenyl ring.