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Study of Binuclear Silicon Complexes of Diketopiperazine at SN2 Reaction Profile
Sohail Muhammad*, Alan R. Bassindale?, Peter G. Taylor?, Louise Male, Simon J. Coles?, and Michael B. HursthouseDepartment of Chemistry and Analytical Sciences, The Open University, Walton Hall, Milton Keynes, MK7 6AA, U.K.
EPSRC National Crystallography Service, School of Chemistry, University of Southampton, Southampton, SO17 1BJ, U.K.
Organometallics, 2011, 30 (3), pp 564-571
DOI: 10.1021/om1009318
Abstract
A series of binuclear pentacoordinate silicon complexes of diketopiperazine have been synthesized and substituent (leaving group) effects on the Si-O bond coordination have been studied by comparison of the five differently substituted analogous structures (X = F, Cl, 0Tf, Br, and I). Variable-temperature NMR spectroscopy supported by X-ray crystallography shows, for the first time in binuclear pentacoordinate silicon complexes, a complex equilibrium with both nonionic (0-Si) and ionic (Si-X) dissociation of the axial bonds in the silicon-centered trigonal bipyramids. The two dissociation pathways are consistent with a model for nucleophilic substitution in a binuclear pentacoordinate silicon compound at the silicon atom.
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