Highly asymmetric coordination of trimethylsilyl groups to tetrazole and triazole rings: an experimental and computational study in gaseous and crystalline phases.
1-Trimethylsilyltetrazole, 1, has been synthesised from chlorotrimethylsilane and tetrazole in the presence of triethylamine as an auxiliary base. The structure of this compound has been determined in the crystalline phase by X-ray diffraction of a crystal grown in situ. The gas-phase structures of 1 and 1-trimethylsilyl-1,2,4-triazole, 2, have been determined by gas-phase electron diffraction (GED). An extensive investigation of these and related compounds by ab initio calculations is also reported. The angles between the rings and the substituents on N were of particular interest. It was found that the calculated difference of 15.5 degrees between the CNSi and NNSi angles in 1 was mostly, but not entirely, an inherent property of the tetrazole ring and not due to a short SiN interaction.
Wann
Derek A
DA
School of Chemistry, University of Edinburgh, West Mains Road, Edinburgh, UKEH9 3JJ.
Gronde
Ingo
I
Foerster
Thomas
T
Hayes
Stuart A
SA
Masters
Sarah L
SL
Robertson
Heather E
HE
Mitzel
Norbert W
NW
Rankin
David W H
DW