Dixit, Arun N. ; Reddy, K. Venodhar ; Rakeeb, Abdul ; Deshmukh, A. S. ; Rajappa, Srinivasachari ; Ganguly, Bishwajit ; Chandrasekhar, Jayaraman (1995) Conformational preferences of α-functionalised keten-S,N-acetals: potential role of SO and SS interactions in solution Tetrahedron, 51 (5). pp. 1437-1448. ISSN 0040-4020
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Official URL: http://linkinghub.elsevier.com/retrieve/pii/004040...
Related URL: http://dx.doi.org/10.1016/0040-4020(94)01023-S
Abstract
PMR spectra of carbonyl compounds 2a-k reveal significant variations in the population of E and Z isomers on changing the solvent from CDCl3 to DMSO-d6. In non-polar media, the intramolecular N-H....O hydrogen bonded form is exclusively observed. In DMSO-d6, 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 = O,S) in these systems. Ab initio calculations support this interpretation.
| Item Type: | Article |
|---|---|
| Source: | Copyright of this article belongs to Elsevier Science. |
| ID Code: | 7109 |
| Deposited On: | 25 Oct 2010 12:34 |
| Last Modified: | 05 Feb 2011 05:37 |
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