V. Kuznetsov
Sep 7, 2011
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Journal
Chemistry of Heterocyclic Compounds
Abstract
Substituted hexahydropyrimidin-2-ones possess a broad spectrum of biological activity and can serve as radioprotectors, immunostimulators, central nervous system regulators, herbicides, and antitumor agents as well as in fine organic synthesis [1–3]. These molecules feature a highly compressed chair ring in the heteroatomic segment [4]. On the other hand, the conformational behavior of these compounds has hardly been studied. In the present work, the HF/6-31G(d) and PBE/3z methods from the HyperChem [5] and PRIRODA [6] program packages, respectively, were used in the first study of the conformational properties of hexahydropyrimidin-2-one and its ammonium and oxonium ions. These molecules, similar to cyclic carbonates [7], display interconversions between two energydegenerate compressed chair forms through a transition state (TS) close to the 2,5-twist form (2,5-T).