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Paper | Special issue | Vol 62, No. 1, 2004, pp.235-249
Published online, 6th May, 2003
DOI: 10.3987/COM-02-S(P)1
Computational Study on Conformational Features of Protonated 5H,7H-Dibenzo[b,g][1,5]dithiocin Oxides by ab initio MO Calculations

Keiji Okada, Masato Tanaka, and Katsuo Ohkata*

*Department of Chemistry, Faculty of Science, Hiroshima University, 1-3-1 Kagamiyama, Higashi-Hiroshima, Hiroshima 739-8526, Japan

Abstract

The ab initio MO calculations with HF/6-31G* basis set were performed in the neutral 5H,7H-dibenzo[b,g][1,5]dithiocin 12-oxide (1), the mono-protonated (1-H+) and the di-protonated (1-2H+) sulfoxides. The calculations indicated that the protonation is very important process for the 1,5-oxygen shift and the oxygen atom approaches to another sulfur by protonation. The inside oxygen conformation (the TBi or the BBi) is important for the intramolecular oxygen shift to form the oxygen-bridged intermediate in 1-2H+-BBb, and the outside oxygen conformation (the TBo or the BBo) is the most probable conformation to form the sulfurane intermediate in 1-2H+-BBo and 2-2H+-BBo, respectively.