Computational study of 1,3-dithiane 1,1-dioxide (1,3-dithiane sulfone). Description of the inversion process and manifestation of stereoelectronic effects on 1JC-H coupling constants

Rafael Notario; María Victoria Roux; Gabriel Cuevas; Julio Cardenas; Verónica Leyva; Eusebio Juaristi

doi:10.1021/jp060463c

Computational study of 1,3-dithiane 1,1-dioxide (1,3-dithiane sulfone). Description of the inversion process and manifestation of stereoelectronic effects on 1JC-H coupling constants

J Phys Chem A. 2006 Jun 22;110(24):7703-12. doi: 10.1021/jp060463c.

Authors

Rafael Notario¹, María Victoria Roux, Gabriel Cuevas, Julio Cardenas, Verónica Leyva, Eusebio Juaristi

Affiliation

¹ Instituto de Química Física Rocasolano, CSIC, Serrano 119, 28006 Madrid, Spain. rnotario@iqfr.csic.es

PMID: 16774218
DOI: 10.1021/jp060463c

Abstract

A theoretical study on the conformational interconversions in 1,3-dithiane 1,1-dioxide (1,3-dithiane sulfone) has been carried out. Nineteen conformations have been considered. Four minima and five transition states have been identified. A description of the inversion-topomerization process of 1,3-dithiane sulfone is presented. Calculations show that two transition states are associated with inversion and three more with topomerization. IGLO calculations of the (1)J(C-H) one-bond coupling constants in 1,3-dithiane sulfone have also been carried out. These constants are compared with those obtained for 1,3-dithiane, thiane, and thiane sulfone and their magnitude is explained in terms of stereoelectronic interactions.