Silacyclohexanes, Sila(hetero)cyclohexanes and Related Compounds: Structure and Conformational Analysis

Bagrat A Shainyan

doi:10.3390/molecules25071624

Silacyclohexanes, Sila(hetero)cyclohexanes and Related Compounds: Structure and Conformational Analysis

Molecules. 2020 Apr 1;25(7):1624. doi: 10.3390/molecules25071624.

Author

Bagrat A Shainyan¹

Affiliation

¹ A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of Russian Academy of Science, 1 Favorsky Street, 664033 Irkutsk, Russia.

Abstract

Conformational analysis of Si-mono- and Si,Si-disubstituted silacyclohexanes as well as their analogues with a heteroatom(s) in the ring is reviewed with the focus on the recent results. Experimental measurements in the gas phase (gas electron diffraction, GED) and low temperature NMR spectroscopy (LT NMR) on ¹H, ¹³C and ²⁹Si nuclei are described along with theoretical calculations at the DFT and MP2 levels of theory. Structural and conformational specific features are shown to be principally different from those of the carbon predecessors - the corresponding cyclohexanes, oxanes, thianes and piperidines. The role of various effects (steric, hyperconjugation, stereoelectronic, electrostatic) is demonstrated.

Keywords: GED; LT NMR; conformational analysis; silicon-containing heterocycles; structure; theoretical calculations.

Publication types

Review

MeSH terms

Cyclohexanes / chemistry*
Models, Molecular*
Molecular Conformation
Molecular Structure
Phase Transition
Spectrum Analysis

Substances

Cyclohexanes