Hydrogen Bonds and Conformations of Dialkyl [1-Hydroxy-3-(dialkylamino)-2,2-dimethylpropyl]phosphonates

Abstract

Dialkyl [1-hydroxy-3-(dialkylamino)-2,2-dimethylpropyl]phosphonates (R 1 O) 2 P(O)CH(OH)CMe 2 CH 2 . NR 2 2 [R 1 = R 2 = Me (I); R 1 = Et, R 2 = Me (II); and R 1 = Me, R 2 = Et (III)], compounds with several competing proton3acceptor groups (NR 2 2 , P=O, and P3O) were studied by means of IR spectroscopy and quantum chemistry. It was established for the first time that, under corresponding conditions, these compounds are conformationally labile and can form various intramolecular and intermolecular hydrogen bonds. Hence, experiments with varied medium, phase state, and temperature revealed a well-resolved n(OH)