ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Quantum chemical investigations of intermolecular hydrogen bonds formed by phenylcarbamates and N-methylacetamide

M. Remko and J. Čižmárik

Department of Pharmaceutical Chemistry, Faculty of Pharmacy, Comenius University, 83232 Bratislava

Abstract: The quantum chemical PCILO method has been used to determine equilibrium geometries and hydrogen bond energies of the l-[2-(2-meth- oxyphenylcarbamoyloxy)ethyl]piperidine (B) and its cation (BH⁺)—N-methylacetamide systems which represent the models for the local anaes­ thetic—lipoprotein part of the nerve membrane interactions. According to our calculations of the complexes local anaesthetic—N-methylacetamide it is the N⁺ —H group of the cationic form of drug which forms the strongest hydrogen bond with the carbonyl group of the N-methylacetamide. This group is able to interrupt the N—H ... 0 = C interpeptide hydrogen bond. The possible consequences of this on the mechanism of action of local anaesthetics are briefly discussed.

Full paper in Portable Document Format: 415a577.pdf

Chemical Papers 41 (5) 577–582 (1987)