Issue 16, 2009

Why are trimethylsilyl groups asymmetrically coordinated? Gas-phase molecular structures of 1-trimethylsilyl-1,2,3-benzotriazole and 2-trimethylsilyl-1,3-thiazole

Abstract

The structures of 1-trimethylsilyl-1,2,3-benzotriazole and 2-trimethylsilyl-1,3-thiazole have been determined by gas electron diffraction and computational methods. While 1-trimethylsilyl-1,2,3-benzotriazole shows a significant asymmetry in the way the SiMe3 groups bonds to the ring system, the same is not true for 2-trimethylsilyl-1,3-thiazole. However, it has been shown that when the positions of formal single and double bonds in the rings systems are considered, the silyl groups in both compounds are displaced towards the neighbouring ring nitrogen atom. Calculated structures of a series of analogous compounds with different substituents on silicon show only minor variations in the extent of the distortion, although with hydrogen instead of a silyl group the displacement is significantly smaller.

Graphical abstract: Why are trimethylsilyl groups asymmetrically coordinated? Gas-phase molecular structures of 1-trimethylsilyl-1,2,3-benzotriazole and 2-trimethylsilyl-1,3-thiazole

Supplementary files

Article information

Article type
Paper
Submitted
10 Dec 2008
Accepted
16 Feb 2009
First published
09 Mar 2009

Dalton Trans., 2009, 3026-3033

Why are trimethylsilyl groups asymmetrically coordinated? Gas-phase molecular structures of 1-trimethylsilyl-1,2,3-benzotriazole and 2-trimethylsilyl-1,3-thiazole

T. Foerster, D. A. Wann, H. E. Robertson and D. W. H. Rankin, Dalton Trans., 2009, 3026 DOI: 10.1039/B822154E

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