N-[hydroxy(dimethyl)silylmethyl]-N,N′-propylene urea hydrochloride: Synthesis and structure

被引：13

作者：

Pestunovich, Vadim A. ^{[1
]}

Albanov, Alexander I. ^{[1
]}

Pogozhikh, Sergey A. ^{[2
]}

Ovchinnikov, Yuri E. ^{[2
]}

Lazareva, Nataliya F. ^{[1
]}

机构：

[1] Russian Acad Sci, AE Favorsky Irkutsk Inst Chem, Siberian Div, Irkutsk 664033, Russia

[2] Novosibirsk State Pedag Univ, Novosibirsk 630128, Russia

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2012年 / 1024卷

关键词：

Pentacoordinate silicon compounds; Protonated silanol; N-(Silylmethyl)-N; N'-propylene ureas; NMR; X-ray; HYPERVALENT SILICON-COMPOUNDS; PROTEASE INHIBITORS; CRYSTAL-STRUCTURE; CARBON BOND; X-RAY; PENTACOORDINATE; HYDROLYSIS; REACTIVITY; CHEMISTRY; SILANOL;

D O I：

10.1016/j.molstruc.2012.05.017

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The new N-chlorodimethylsilylmethyl-N'-trimethylsilyl-N,N'-propylene urea 5 was synthesized by trans-silylation reaction of N,N'-bis(trimethylsilyl)-N,N'-propylene urea 4 with CICH2SiMe2Cl. Mild hydrolysis of compound 5 results in the formation of N-[hydroxy(dimethyl)silylmethyl]-N,N'-propylene urea hydrochloride 6. The structure of the studied compounds in solution was determined by H-1, C-13 and Si-29 NMR spectroscopy and by X-ray analysis in the solid state. The results of these studies are indicative of pentacoordination of the silicon atoms in ureas S and 6. Compound 6 is a new example of poorly known protonated silanols with hypervalent silicon atom. (C) 2012 Elsevier B.V. All rights reserved.

引用

页码：136 / 141

页数：6

共 54 条

[1]

Albanov A.I., 1999, 12 INT S ORG CHEM SE

[2] Mechanistic studies on the catalytic cycle of metal fluoride-catalyzed allylation using allyltrimethoxysilane in protic solvents [J].

Aoyama, N ;

Hamada, T ;

Manabe, K ;

Kobayashi, S .

JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (19) :7329-7333

[3] Modelling nucleophilic substitution at silicon using hypervalent silicon compounds based on urea ligands [J].

Bassindale, AR ;

Glynn, SJ ;

Taylor, PG ;

Auner, N ;

Herrschaft, B .

JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2001, 619 (1-2) :132-140

[4] The ozonation of silanes and germanes: An experimental and theoretical investigation [J].

Cerkovnik, J ;

Tuttle, T ;

Kraka, E ;

Lendero, N ;

Plesnicar, B ;

Cremer, D .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (12) :4090-4100

[5] Structural influence of a sulfonyl group in eight-membered rings of diorganosilanes [J].

Chandrasekaran, A ;

Day, RO ;

Holmes, RR .

ORGANOMETALLICS, 1996, 15 (14) :3189-3197

[6] Recent developments in the synthesis and structure of organosilanols [J].

Chandrasekhar, V ;

Boomishankar, R ;

Nagendran, S .

CHEMICAL REVIEWS, 2004, 104 (12) :5847-5910

[7] REACTIVITY OF PENTACOORDINATE AND HEXACOORDINATE SILICON-COMPOUNDS AND THEIR ROLE AS REACTION INTERMEDIATES [J].

CHUIT, C ;

CORRIU, RJP ;

REYE, C ;

YOUNG, JC .

CHEMICAL REVIEWS, 1993, 93 (04) :1371-1448

[8] Recent Developments in the Chemistry of Cubic Polyhedral Oligosilsesquioxanes [J].

Cordes, David B. ;

Lickiss, Paul D. ;

Rataboul, Franck .

CHEMICAL REVIEWS, 2010, 110 (04) :2081-2173

[9] Recent developments of molecular chemistry for sol-gel processes [J].

Corriu, RJP ;

Leclercq, D .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1996, 35 (13-14) :1420-1436

[10] ROLE OF PENTACOORDINATE INTERMEDIATES IN THE HYDROLYSIS REACTION OF ORGANIC SILICATES [J].

CORRIU, RJP ;

GUERIN, C ;

HENNER, BJL ;

WANG, Q .

ORGANOMETALLICS, 1991, 10 (09) :3200-3205

← 1 2 3 4 5 6 →