THEORETICAL-STUDY OF HYDROGEN-BONDING IN THE 1-HYDROPEROXY-1-(P-NITROPHENYL)ETHANOL

A rather unusual stability was found experimentally for the title comp ound and it is suggested that intramolecular hydrogen bonding could be responsible for such behavior. We performed a theoretical examination of its electronic structure, paying special attention to analyzing fo r the possibility of hydrogen bonding and the influence of different s ubstituents attached to the C-atom bearing the hydroperoxy and hydroxy l groups. We made semi-empirical and ab initio calculations and, in bo th cases, we found the existence of intramolecular hydrogen bonding wh ich seems to support the atypical physical properties of the title com pound. (C) 1998 Elsevier Science B.V. All rights reserved.