The Journal of Organic Chemistry

N-Nitroamides and N-Nitrocarbamates. III. Rotational Isomerism, Steric Effects, and Physical Properties at Low Temperatures1

EH White, MC Chen, LA Dolak

Index: White,E.H. et al. Journal of Organic Chemistry, 1966 , vol. 31, p. 3038 - 3046

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Citation Number: 21

Abstract

Infrared, ultraviolet, and nuclear magnetic resonance spectra (at room temperature and at low temperatures), solvent effects, and substituent effects have been used to show that the double carbonyl peaks of the N-nitrocarbamates stem from rotational isomerism involving the carboxyl groups, and not from Fermi resonance. Cyclic nitrocarbamates in which this type of rotation is impossible have only a single carbonyl band in the infrared. The rotation ...