Electrostatic effects on conformational equilibria: Alkyl 2-cyanobenzoates and 3-cyanopropenoates

O Exner, Z Friedl, P Fiedler

Index: Exner, Otto; Friedl, Zdenek; Fiedler, Pavel Collection of Czechoslovak Chemical Communications, 1983 , vol. 48, # 11 p. 3086 - 3096

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Citation Number: 9

Abstract

Abstract The conformational equilibrium ap⇌ sp of the title compounds was investigated by two methods: dipole moment measurement in benzene solution and IR spectroscopy of the carbonyl band in decahydronaphthalene solution. Approximately 71% of the ap rotamers were found for 2-cyanobenzoates (II, III), and between 60 to 80% for (Z)-3- cyanopropenoates (V, VI). This result does not reveal any special attractive interaction ...