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Thermodynamically controlled Reactions of Selenenylphosphonium Ion Me3PSeMe+ toward Electrophiles and Nucleophiles
* 1 , 2 , 1
1  Karl-Franzens-Universität, Institut für Chemie, Schuberststraße 1, A-8010 Graz, Austria
2  Karl-Franzens-Universität, Institut für Molekulare Biowissenschaften, Heinrichstraße 31a, A-8010 Graz, Austria

Abstract: Lewis base adducts with selenenyl halides have been investigated experimentally and theoretically as models for interactions that might be relevant for the activity of Glutathione peroxidase (GPx).[1-3] Recently, we have shown that in donor adducts of selenenium ions with amines or phosphanes the formal donor-acceptor bond is covalent rather than dative.[4] Our findings suggested that in contrast to the description of adducts of the isolobal arsenium ions a description as selenenyl phosphonium and selenenyl ammonium ions appears more appropriate (Scheme 1). We also prepared compounds containing the selenenylphosphonium ion on a synthetic scale and studied their spectroscopic and chemical behaviour.[5] Here we describe ab-initio calculations exploring the reactivity of methyl substituted selenenyl phosphonium ions towards some simple nucleophiles and electrophiles.
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