The ring-opening of an unsymmetrical tetrahedral intermediate - 2-hydroxy-1,3-oxathiolane |
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| Authors: | Linda J Santry Raymond A Poirier Robert A McClelland Imre G Csizmadia |
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| Institution: | (1) Department of Chemistry, University of Toronto, M5S 1A1 Toronto, Ontario, Canada;(2) Physical Sciences Division, Scarborough College, University of Toronto, M1C 1A4 West Hill, Ontario |
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| Abstract: | Ab initio calculations were performed on 2-hydroxy-1,3-oxathiolane: and the two products of its breakdown: Complete geometry optimizations were performed at minimal (STO-3G) and split-valence (3-21G) basis set levels. In addition, a single point calculation was performed at 6-31G* level withd orbitals added on sulfur only. The conformation of the oxathiolane intermediate and its stability relative to the breakdown products was investigated. The STO-3G basis set gave an envelope form while 3-21G gave the twist form of the five-membered ring as the most stable. For all three basis sets the ester product was more stable than thioester. |
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| Keywords: | Ab initio calculations tetrahedral intermediate 2-hydroxy-1 3-oxathiolane sulfur-containing compounds |
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