The Journal of Organic Chemistry

Steric and electronic effects in SN2 reactions of 9-substituted fluorenyl and. alpha.-cyano carbanions with benzyl chloride in dimethyl sulfoxide solution

FG Bordwell, DL Hughes

Index: Bordwell, Frederick G.; Hughes, David L. Journal of Organic Chemistry, 1983 , vol. 48, # 13 p. 2206 - 2215

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Citation Number: 32

Abstract

Rates of reactions of PhCHpCl with carbanions derived from six a-cyano carbon acids of varied structure with pK, values ranging over 16 units have been measured. When placed on a log k vs. pK, plot the points fit near to the extended Brernsted line obtained earlier for the 9-(methoxycarbony1) fluorenyl ion family, 9-CO2MeF1-, reacting with PhCH2C1. It is concluded that differences in shape, size, charge concentration, solvation, or aromaticity ...