CONFORMATIONAL PREFERENCES OF ALPHA-FUNCTIONALIZED KETEN-S,N-ACETALS - POTENTIAL ROLE OF S..O AND S..S INTERACTIONS IN SOLUTION

被引：27

作者：

DIXIT, AN

REDDY, KV

DESHMUKH, ARAS

RAJAPPA, S

GANGULY, B

CHANDRASEKHAR, J

机构：

[1] NATL CHEM LAB,DIV ORGAN CHEM,POONA 411008,MAHARASHTRA,INDIA

[2] INDIAN INST SCI,DEPT ORGAN CHEM,BANGALORE 560012,KARNATAKA,INDIA

来源：

TETRAHEDRON | 1995年 / 51卷 / 05期

关键词：

D O I：

10.1016/0040-4020(94)01023-S

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

PMR spectra of carbonyl compounds 2a-k reveal significant variations in the population off and Z Isomers on changing the solvent from CDCl3 to DMSO-d(6). In non-polar media, the intramolecular N-H....O hydrogen bonded form is exclusively observed. In DMSO-d(6), the alternative Z form is also populated. A similar conformational switch is also noted in the corresponding thiones. Different interpretations are critically analysed. The most consistent explanation is suggested to involvean interplay of N-H....X hydrogen bonding and S...X attractive interaction (X=0,S) in these systems. Ah initio calculations support this interpretation.

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页码：1437 / 1448

页数：12

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