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Intramolecular hydrogen bonding in imidazole‐4(5)‐alkoxycarbonyl‐5(4)‐carboxamide derivatives
Author(s) -
Yasuda Naohiko,
Nakamura Asao,
Tsuboi Masamichi
Publication year - 1987
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570240202
Subject(s) - chemistry , imidazole , intramolecular force , ring (chemistry) , hydrogen bond , amide , carboxamide , hydrogen atom , carbonyl group , medicinal chemistry , hydrogen , stereochemistry , photochemistry , group (periodic table) , molecule , organic chemistry
The ir spectrum of imidazole derivatives, which have an alkoxycarbonyl group and a carboxamide group at the 4‐ and 5‐positions of the imidazole ring respectively, exhibits the shift of the ester carbonyl band to a lower wave number. This phenomenon was investigated by spectroscopic measurements of a group of relevant compounds. The results indicate that the shift is caused by the intramolecular hydrogen bonds between the hydrogen atom of the amide and the carbonyl oxygen of the ester which is enhanced by the resonance stabilization of the imidazole ring.