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

Content Provider	Royal Society of Chemistry (RSC)
Author	Baukov, Yuri I. Arkhipov, Dmitry E. Lagunin, Alexey A. Negrebetsky, Vadim V. Korlyukov, Alexander A. Kramarova, Eugenia P. Shipov, Alexander G. Bylikin, Sergey Yu. Bassindale, Alan R. Taylor, Peter G. Nikolin, Alexey A.
Copyright Year	2016
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.
Starting Page	75315
Ending Page	75327
Page Count	13
File Format	HTM / HTML PDF
ISSN	20462069
Volume Number	6
Issue Number	79
Journal	RSC Advances
DOI	10.1039/c6ra14450k
Language	English
Publisher	Royal Society of Chemistry
Access Restriction	Open
Subject Keyword	Hydrolysis X-ray crystallography Boron trifluoride Solvation Isomerization Tetracoordinate Krypton difluoride Covalent bond In silico Nuclear magnetic resonance
Content Type	Text
Resource Type	Article
Subject	Chemistry Chemical Engineering

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

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