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2005•Australian Journal of ChemistryRequires access

The Role of Ylides in the Chlorination of Unsymmetrical Sulfides: An Ab Initio Molecular Orbital Study

Michael A. Potvin, Belquis Mothana, L. Albrecht, Katherine Valenta Darvesh, Richard Francis Langler

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Abstract

Ab initio molecular orbital theory has been used to investigate a series of possible chlorosulfonium ylides to assess the potential for ylide intermediacy in the chlorination of organic sulfides. The majority of optimized structures are best viewed as thionium salts. Only ylide structures in which the putative carbanionic centre bears a powerful anion stabilizer (e.g. cyano or carbomethoxy) survive optimization.

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What this paper is about

Ab initio molecular orbital theory has been used to investigate a series of possible chlorosulfonium ylides to assess the potential for ylide intermediacy in the chlorination of organic sulfides. The majority of optimized structures are best viewed as thionium salts. Only ylide structures in which the putative carbanionic centre bears a powerful anion stabilizer (e.g. cyano or carbomethoxy) survive optimization.

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Available abstract

Ab initio molecular orbital theory has been used to investigate a series of possible chlorosulfonium ylides to assess the potential for ylide intermediacy in the chlorination of organic sulfides. The majority of optimized structures are best viewed as thionium salts. Only ylide structures in which the putative carbanionic centre bears a powerful anion stabilizer (e.g. cyano or carbomethoxy) survive optimization.

Key concepts: Ylide, Ab initio, Chemistry, Ab initio quantum chemistry methods, Computational chemistry, Molecular orbital, Supramolecular chemistry, Quantum chemistry

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