Intra- and intermolecular coordination reactions in solution involving pentacoordinated fluorosilanes based on proline

• Published in: Russian chemical bulletin 2013-08, Vol.62 (8), p.1892-1899
• Main Authors: Nikolin, A. A., Kuznetsova, O. V., Arkhipov, D. E., Kramarova, E. P., Shipov, A. G., Egorochkin, A. N., Korlyukov, A. A., Baukov, Yu. I., Negrebetskii, Vad. V.
• Format: Article
• Language: English
• Subjects: Chemistry; Chemistry and Materials Science; Chemistry/Food Science; Full Articles; Inorganic Chemistry; Organic Chemistry
• ISSN: 1066-5285; 1573-9171
• DOI: 10.1007/s11172-013-0272-1

NMR spectroscopy was used to study a series of C,O-monochelate N ′-(fluorodimethyl-silylmethyl)- N ′-methyl- N -(organosulfonyl)proline amides in the solid state and in solutions in chloroform, pyridine, and acetone. The structure of one of the complexes was established by X-ray crystallography. Quantum chemical calculations were performed to interpret the spectral data obtained. The molecular conformation observed in crystal was found to be retained in solutions. The coordination bonds of silicon atom with acetone and pyridine are very weak and cannot stabilize the acyclic form (without the Si-O coordination bond). The 29 Si chemical shift was found to be directly dependent on the Si-O bond distance. The mutual influence of organosulfonyl group and chelate ring was described in terms of polarization effects.