The isolation and structure of a highly stable, metallation-resistant and multiply hydrogen-bonded sulfonylamide-phosphine oxide adduct, PhSO(2)CH(2)C(=O)NH2 center dot O=P(NMe(2))(3), PSA center dot HMPA (PSA=phenylsulfonylacetamide, HMPA=hexamethylphosphoramide)

被引：7

作者：

CraggHine, I ^{[1
]}

Davidson, MG ^{[1
]}

Edwards, AJ ^{[1
]}

Lamb, E ^{[1
]}

Raithby, PR ^{[1
]}

Snaith, R ^{[1
]}

机构：

[1] UNIV CAMBRIDGE,DEPT CHEM,CAMBRIDGE CB2 1EW,ENGLAND

来源：

CHEMICAL COMMUNICATIONS | 1996年 / 02期

关键词：

D O I：

10.1039/cc9960000153

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Attempted metallations of the expectedly acidic sulfonylamide (PSA) in the presence of the phosphine oxide HMPA all fail, giving instead the very stable 1:1 adduct PSA . HMPA; its solid-state structure consists of layers of PSA molecules linked by intercalated HMPA molecules, such aggregation resulting in particular from a large number of significant C-H ... O hydrogen-bonding interactions per PSA . HMPA unit.

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页码：153 / 154

页数：2

相关论文

共 13 条

[1] THE HYDROGEN-BOND AND CRYSTAL ENGINEERING [J].

AAKEROY, CB ;

SEDDON, KR .

CHEMICAL SOCIETY REVIEWS, 1993, 22 (06) :397-407

[2] ISOLATION, STRUCTURE AND MO CALCULATIONAL INVESTIGATIONS OF A HIGHLY STABLE, HYDROGEN-BONDED PRIMARY AMINE PHOSPHINE OXIDE ADDUCT, 2-AMINOBENZOTHIAZOLE HMPA, C6H4SC(=N)NH2.O=P(NME2)3 - A POSSIBLE MODEL TO EXPLAIN THE CARCINOGENICITY OF HMPA (HMPA = HEXAMETHYLPHOSPHORAMIDE) [J].

ARMSTRONG, DR ;

BENNETT, S ;

DAVIDSON, MG ;

SNAITH, R ;

STALKE, D ;

WRIGHT, DS .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (03) :262-264

[3] PATTERNS IN HYDROGEN BONDING - FUNCTIONALITY AND GRAPH SET ANALYSIS IN CRYSTALS [J].

BERNSTEIN, J ;

DAVIS, RE ;

SHIMONI, L ;

CHANG, NL .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (15) :1555-1573

[4] THE C-H...O HYDROGEN-BOND IN CRYSTALS - WHAT IS IT [J].

DESIRAJU, GR .

ACCOUNTS OF CHEMICAL RESEARCH, 1991, 24 (10) :290-296

[5] VERY STRONG HYDROGEN-BONDING [J].

EMSLEY, J .

CHEMICAL SOCIETY REVIEWS, 1980, 9 (01) :91-124

[6] GENERATION OF A THIOALDEHYDE S-OXIDE (SULFINE) BY RETRO-DIELS-ALDER REACTIONS [J].

FREER, AA ;

KIRBY, GW ;

LEWIS, RA .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (10) :718-719

[7] STRUCTURES OF ORGANONITROGEN LITHIUM COMPOUNDS - RECENT PATTERNS AND PERSPECTIVES IN ORGANOLITHIUM CHEMISTRY [J].

GREGORY, K ;

SCHLEYER, PV ;

SNAITH, R .

ADVANCES IN INORGANIC CHEMISTRY, 1991, 37 :47-142

[8]

Hamilton A., 1995, TETRAHEDRON, V51, P343

[9] CYCLIZATION OF GAMMA-DELTA UNSATURATED SULFENIC ACIDS TO GIVE THIETAN 1-OXIDE DERIVATIVES - CRYSTAL-STRUCTURE OF REL-(1R,2S,3R,4R)-3-HEXYL-2-HYDROXYMETHYL-4-METHYLTHIETAN 1-OXIDE [J].

JONES, DN ;

KOGAN, TP ;

MURRAYRUST, P ;

MURRAYRUST, J ;

NEWTON, RF .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1982, (06) :1325-1332

[10] MELDOLA MEDAL LECTURE - RING-STACKING AND RING-LADDERING IN ORGANONITROGENLITHIUM COMPOUNDS - THE DEVELOPMENT OF CONCEPTS WITH WIDE APPLICABILITY THROUGHOUT LITHIUM STRUCTURAL CHEMISTRY [J].

MULVEY, RE .

CHEMICAL SOCIETY REVIEWS, 1991, 20 (02) :167-209