MO study of molecular association of local anaesthetics of carbamate type

Abstract

The quantum-chemical PCILO method has been used to study of molecular association of piperidinoethyl alkoxyphenylcarbamates. The self-association of this type of compounds has been studied with methyl phenylcarbamate as a simple model. The PCILO calculations indicate the open dimer with N-H...O=C hydrogen bond to be the most stable complex. Moreover, the PCILO method has been used fro study of intermolecular hydrogen bonds formed between oxygen and nitrogen atoms of -NH-COO- group of the title compounds and N-methylacetamide, N,N-dimethylacetamide, and phenol. The calculations have shown that the most stable hydrogen bonds are formed by carbonyl oxygen atom. Somewhat weaker hydrogen bonds are formed by N-H group. The weakest hydrogen bonds are formed by methoxyl oxygen atom of the -NH-COO- part of the drug.