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Australian Journal of Chemistry Australian Journal of Chemistry Society
An international journal for chemical science
RESEARCH ARTICLE

Intramolecular hydrogen bonding in ortho-substituted N,N-dimethylbenzamides

CW Fong

Australian Journal of Chemistry 33(6) 1285 - 1290
Published: 1980

Abstract

Intramolecular hydrogen bonding in o-hydroxy-, o-amino- and o-mercapto- N,N-dimethylbenzamide has been examined with the help of 1H, 13C n.m.r. and infrared spectroscopy, a study of barriers to rotation about the C- N bond, and a study of substituent effects using a multi-substituent parameter equation. The cyclic intramolecular hydrogen-bonded structure for the o-mercapto compound is non-planar, and conformational isomers have been detected. The order of relative energies of the hydrogen bonds formed in o-substituted N,N-dimethylbenzamides is OH > NH2 > SH, as determined from a rotational barrier probe. It has beenverified that intramolecular hydrogen bonding causes a downfield shift of the 13C n.m.r. chemical shift of the carbonyl group in these compounds.

https://doi.org/10.1071/CH9801285

© CSIRO 1980

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