Abstract
2-, 3-, 4-, 5-, 6-, 7- and 8-trimethylsilylquinolines and their methiodides as well as some 2-silyl-alkylquinolines 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-centered 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 interactions is observed in 8-trimethylsilylquinoline.
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