Carbon-silicon hyperconjugation X-ray structural study of N-methyl-4-trimethylsilylmethylpyridinium triflate

Abstract

Hyperconjugation between the CH2-Si bond and the charged pyridinium π system in the N-methyl 4-trimethylsilylmethyl pyridinium ion (8), manifests in the crystal structure as lengthening of the CH2-Si bond, shortening of the CH2-Cipso bond and smaller but systematic effects on the C-C bond distances within the pyridinium ring. The structural effects are supported in solution by systematic effects on the 29Si-13C and 13C-13C one-bond coupling constants. © 2002 Elsevier Science B.V. All rights reserved.