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RESEARCH ARTICLE
Contents Vol 66(10)

‘Classical’ and ‘Abnormal’ Bonding in Tin (ii) N-Heterocyclic Carbene Complexes

Robert S. P. Turbervill A and Jose M. Goicoechea A B
+ Author Affiliations
- Author Affiliations

A Department of Chemistry, University of Oxford, Chemistry Research Laboratory, Mansfield Road, Oxford, OX1 3TA, UK.

B Corresponding author. Email: jose.goicoechea@chem.ox.ac.uk

Australian Journal of Chemistry 66(10) 1131-1137 https://doi.org/10.1071/CH13115
Submitted: 8 March 2013  Accepted: 2 April 2013   Published: 26 April 2013

Abstract

Reaction of Sn(OTf)2 (OTf– = OSO2CF3–) with one and two equivalents of the N-heterocyclic carbene (NHC) 1,3-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene (IPr) yielded the complexes [Sn(IPr)(OTf)2] (1) and [Sn(IPr)(aIPr)(OTf)][OTf] (2), respectively. Both species were characterised by single crystal X-ray diffraction, multi-element NMR spectroscopy, and elemental analysis. Both compounds display an NHC ligand bonded to the tin(ii) metal centre via the C2 carbon in a ‘classical’ mode, while 2 also contains an ‘abnormal’ C4/C5-bonded carbene (aIPr). These observations highlight the subtle steric and electronic effects affecting the coordination modes of these ligands. Solution phase NMR experiments on 1 and 2 reveal complex behaviour resulting in the protonation of the IPr ligands to yield the 1,3-bis(2,6-diisopropylphenyl)-imidazolium cation via an unidentified reaction mechanism.


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