
TY  - JOUR
A1  - Fong, CW 
T1  - Intramolecular hydrogen bonding in <I>ortho</I>-substituted N,N-dimethylbenzamides
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1980
VL  - 33
IS  - 6
SP  - 1285
EP  - 1290
KW  - 
UR  - https://doi.org/10.1071/CH9801285 
N2  - 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. 
ER  -

