Spectral study of hydrogen bonding in monopotassium salts of cycloalkane 1 : 1 dicarboxylic acids

Abstract

A strong nearly symmetrical intramolecular hydrogen bond was found in cyclopropane 1 : 1 dicarboxylic acid monopotassium salts as compared with an intermolecular asymmetrical hydrogen bond in the cyclobutane and cyclopentane 1 : 1 dicarboxylic acid monopotassium salts. An angle of 120° between the two carboxylic groups appears to be responsible for the strong hydrogen bonding in the former. The ¹³C chemical shift of the C₃ carbon atom was found to be highly dependent on the angle between the two carboxylic groups.