Experimental and theoretical studies of substituent effects in hydrogen bond based molecular recognition of a zwitterion by substituted arylureas

CS Wilcox, E Kim, D Romano, LH Kuo, AL Burt…

Index: Wilcox, Craig S.; Kim, Eun-il; Romano, David; Kuo, Lung Huang; Burt, Arthur L.; Curran, Dennis P. Tetrahedron, 1995 , vol. 51, # 2 p. 621 - 634

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Citation Number: 128

Abstract

Electron withdrawing groups have a strong effect on hydrogen bonding to aryl ureas. The effect of para substituents modestly exceeds the effect of meta substituents. Among common substituent parameters, σ−(ϱ= 1.77, r2= 0.988) is found to be the best predictor for the observed effects of para substituents in aryl ureas. Semi-empirical and ab initio methods are used to calculate charge distributions in substituted benzene derivatives and in these ...