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Study of binuclear silicon complexes of Diketopiperazine at SN2 reaction profile

Study of binuclear silicon complexes of Diketopiperazine at SN2 reaction profile
Study of binuclear silicon complexes of Diketopiperazine at SN2 reaction profile
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.
organometallic compounds, organometalloidal compounds
0276-7333
564-571
Muhammad, Sohail
fc2587b4-fbc4-4f08-8da3-7b24e4c25910
Bassindale, Alan R.
285ee4e0-58d0-4178-a0d9-d7e0d1efbebd
Taylor, Peter G.
e59508fd-4cfb-422c-bbb0-b70cfb6aa195
Male, Louise
723b0bb7-1e60-4357-8587-7d971f3d3ed6
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da
Muhammad, Sohail
fc2587b4-fbc4-4f08-8da3-7b24e4c25910
Bassindale, Alan R.
285ee4e0-58d0-4178-a0d9-d7e0d1efbebd
Taylor, Peter G.
e59508fd-4cfb-422c-bbb0-b70cfb6aa195
Male, Louise
723b0bb7-1e60-4357-8587-7d971f3d3ed6
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Hursthouse, Michael B.
57a2ddf9-b1b3-4f38-bfe9-ef2f526388da

Muhammad, Sohail, Bassindale, Alan R., Taylor, Peter G., Male, Louise, Coles, Simon J. and Hursthouse, Michael B. (2011) Study of binuclear silicon complexes of Diketopiperazine at SN2 reaction profile. Organometallics, 30 (3), 564-571. (doi:10.1021/om1009318).

Record type: Article

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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More information

Published date: 11 January 2011
Keywords: organometallic compounds, organometalloidal compounds
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry, Faculty of Natural and Environmental Sciences

Identifiers

Local EPrints ID: 346143
URI: http://eprints.soton.ac.uk/id/eprint/346143
ISSN: 0276-7333
PURE UUID: bed17d69-9f8e-4213-a5a4-7712d1c952ed
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

Catalogue record

Date deposited: 07 Jan 2013 10:09
Last modified: 18 Feb 2021 16:53

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Contributors

Author: Sohail Muhammad
Author: Alan R. Bassindale
Author: Peter G. Taylor
Author: Louise Male
Author: Simon J. Coles ORCID iD

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