Synthesis and 1H, 13C, 14N, 15N, 29Si NMR study of trimethylsilylquinolines and their methiodides

Article abstract of DOI:10.1016/0022-328X(91)83116-L

2-, 3-, 4-, 5-, 6-, 7-, and 8-trimethylsilylquinolines and their methiodides as well as some 2-silylalkylquinolines were obtained by lithium synthesis in order to elucidate intramolecular donor-acceptor interactions between nitrogen and silicon atoms. 1H, 13C, 14N, 15N and 29Si NMR spectra of the compounds were studied and quantum-chemical calculation of charges on individual atoms in the unsubstituted quinoline and in trimethylsilylquinoline molecule was carried out.The two-centred component of the total system energy for various bonds was calculated.The findings suggest donor-acceptor interaction between nitrogen and silicon atoms in 2-trimethylsilylquinoline that reduces electron density at nitrogen atoms.An apparently weaker interaction is observed in 8-trimethylsilylquinoline.