Study of binuclear silicon complexes of diketopiperazine at S(N)2 reaction profile

Muhammad, Sohail; Bassindale, Alan R.; Taylor, Peter G.; Male, Louise; Coles, Simon and Hursthouse, Michael B. (2011). Study of binuclear silicon complexes of diketopiperazine at S(N)2 reaction profile. Organometallics, 30(3) pp. 564–571.

DOI: https://doi.org/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, OTf, 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 (O-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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