Study of binuclear silicon complexes of diketopiperazine at SN2 reaction profile

Muhammad Sohail, Alan R. Bassindale, Peter G. Taylor, Louise Male, Simon J. Coles, Michael B. Hursthouse

Research output: Contribution to journalArticle

23 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)564-571
Number of pages8
JournalOrganometallics
Volume30
Issue number3
DOIs
Publication statusPublished - 14 Feb 2011
Externally publishedYes

Fingerprint

Diketopiperazines
Silicon
silicon
profiles
Silicon Compounds
dissociation
silicon compounds
X ray crystallography
Nuclear magnetic resonance spectroscopy
crystallography
Substitution reactions
substitutes
Atoms
nuclear magnetic resonance
spectroscopy
atoms
x rays
Temperature
temperature

ASJC Scopus subject areas

  • Organic Chemistry
  • Physical and Theoretical Chemistry
  • Inorganic Chemistry

Cite this

Sohail, M., Bassindale, A. R., Taylor, P. G., Male, L., Coles, S. J., & Hursthouse, M. B. (2011). Study of binuclear silicon complexes of diketopiperazine at SN2 reaction profile. Organometallics, 30(3), 564-571. https://doi.org/10.1021/om1009318

Study of binuclear silicon complexes of diketopiperazine at SN2 reaction profile. / Sohail, Muhammad; Bassindale, Alan R.; Taylor, Peter G.; Male, Louise; Coles, Simon J.; Hursthouse, Michael B.

In: Organometallics, Vol. 30, No. 3, 14.02.2011, p. 564-571.

Research output: Contribution to journalArticle

Sohail, M, Bassindale, AR, Taylor, PG, Male, L, Coles, SJ & Hursthouse, MB 2011, 'Study of binuclear silicon complexes of diketopiperazine at SN2 reaction profile', Organometallics, vol. 30, no. 3, pp. 564-571. https://doi.org/10.1021/om1009318
Sohail M, Bassindale AR, Taylor PG, Male L, Coles SJ, Hursthouse MB. Study of binuclear silicon complexes of diketopiperazine at SN2 reaction profile. Organometallics. 2011 Feb 14;30(3):564-571. https://doi.org/10.1021/om1009318
Sohail, Muhammad ; Bassindale, Alan R. ; Taylor, Peter G. ; Male, Louise ; Coles, Simon J. ; Hursthouse, Michael B. / Study of binuclear silicon complexes of diketopiperazine at SN2 reaction profile. In: Organometallics. 2011 ; Vol. 30, No. 3. pp. 564-571.
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