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Conformational Analysis of Methyl Phenylcarbamate and its Methoxy Derivatives by MO Calculations
Author(s) -
Remko Milan,
Frecer Vladimír,
Čižmárik Jozef
Publication year - 1983
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19833160105
Subject(s) - chemistry , conformational isomerism , planarity testing , carbamate , ring (chemistry) , stereochemistry , group (periodic table) , computational chemistry , benzene , methyl group , crystallography , molecule , organic chemistry
The semi‐empirical PCILO method has been used to determine stable conformations of methyl phenylcarbamate and its m ‐ and p ‐methoxy derivatives as model compounds of the local anesthetics of the carbamate type. The calculations show that the most stable conformations correspond to the nonplanar conformers in which the carbamate group is twisted by 35 degrees out of the plane of the benzene ring. The carbamate group is nonplanar, but the deviation from planarity is small. The stereochemistry of the carbamate group is independent of the m ‐ and p ‐methoxy substitution. The results of the calculations are compared with experimental data. The electron distributions of the most stable conformers were calculated by the semi empirical INDO method.