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On the selenepin/benzene selenide valence tautomerizations: electronic and steric effects at theoretical levels

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Abstract

Tautomerization in selenepin (1) benzene⇌selenide (2) binary system is found to favor, 2, at HF, MP2, and B3LYP levels, using 6-311G* basis set. Electronic effects appear to have small effects on 1⇌2 equilibria and show little impact on the conformational ring inversions of 1, at the same levels. In contrast, steric effects effectively decrease ∆H values in an order inversely proportional to the size of the substituents employed (Me > Et > i-Pr). A possible Se extrusion is suggested to be the main reason why no 2 has ever been detected experimentally.

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Acknowledgments

We wish to thank M. Ghambarian, H. Arefrad, and S. Soleimani-Amiri for many stimulating and helpful discussions.

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  1. Department of Chemistry, Tarbiat Modarres University, P.O. Box 14155-175, Tehran, Iran

    M. Z. Kassaee, S. M. Musavi & M. Majdi

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  1. M. Z. Kassaee
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Correspondence to M. Z. Kassaee.

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Kassaee, M.Z., Musavi, S.M. & Majdi, M. On the selenepin/benzene selenide valence tautomerizations: electronic and steric effects at theoretical levels. Struct Chem 20, 369–376 (2009). https://doi.org/10.1007/s11224-008-9396-6

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