N,N-bis-(dimethylfluorosilylmethyl)amides of N-organosulfonylproline and sarcosine: synthesis, structure, stereodynamic behaviour and in silico studies

Nikolin, Alexey A.; Kramarova, Eugenia P.; Shipov, Alexander G.; Baukov, Yuri I.; Negrebetsky, Vadim V.; Arkhipov, Dmitry E.; Korlyukov, Alexander A.; Lagunin, Alexey A.; Bylikin, Sergey Yu.; Bassindale, Alan R. and Taylor, Peter G. (2016). N,N-bis-(dimethylfluorosilylmethyl)amides of N-organosulfonylproline and sarcosine: synthesis, structure, stereodynamic behaviour and in silico studies. RSC Advances, 2016(79) pp. 75315–75327.

DOI: https://doi.org/10.1039/c6ra14450k

Abstract

(O→Si)-Chelate difluorides R3R2NCH(R1)C(O)N(CH2SiMe2F)2 (9a–c, R1R2 = (CH2)3, R3 = Ms (a), Ts (b); R1 = H, R2 = Me, R3 = Ms (c)), containing one penta- and one tetracoordinate silicon atoms were synthesized by silylmethylation of amides R3R2NCH(R1)C(O)NH2, subsequent hydrolysis of unstable intermediates R3R2NCH(R1)C(O)N(CH2SiMe2Cl)2 (7a–c) into 4-acyl-2,6-disilamorpholines R3R2NCH(R1)C(O)N(CH2SiMe2O)2 (8a–c) and the reaction of the latter compounds with BF3·Et2O. The structures of disilamorpholines 8a,c and difluoride 9a were confirmed by an X-ray diffraction study. According to the IR and NMR data, the O→Si coordination in solutions of these compounds was weaker than that in the solid state due to effective solvation of the Si–F bond. A permutational isomerisation involving an exchange of equatorial Me groups at the pentacoordinate Si atom in complexes 9a–c was detected, and its activational parameters were determined by 1H DNMR. In silico estimation of possible pharmacological effects and acute rat toxicity by PASS Online and GUSAR Online services showed a potential for their further pharmacological study.

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