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Issue 74, 2005

C–H⋯O Hydrogen bonding induced conformation of (S,S)-1,3-benzenedisulfonyl bis[(4S)-4-(ethyl ester)-oxazolidin-2-one]

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Abstract

The conformational arrangement of (S,S)-1,3-benzenedisulfonyl bis[(4S)-4-(ethyl ester)-oxazolidin-2-one] was examined by X-ray crystallography. This revealed an unusual conformational arrangement held together by an internal C–H⋯O[double bond, length as m-dash]C hydrogen bond. Computational modelling has revealed the native conformer to be 16.94 kJ mol−1 more stable than an open conformation.

Graphical abstract: C–H⋯O Hydrogen bonding induced conformation of (S,S)-1,3-benzenedisulfonyl bis[(4S)-4-(ethyl ester)-oxazolidin-2-one]

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Publication details

The article was received on 04 Apr 2005, accepted on 29 Jun 2005 and first published on 06 Jul 2005


Article type: Paper
DOI: 10.1039/B504667J
Citation: CrystEngComm, 2005,7, 454-457
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    C–H⋯O Hydrogen bonding induced conformation of (S,S)-1,3-benzenedisulfonyl bis[(4S)-4-(ethyl ester)-oxazolidin-2-one]

    D. M. Benoit, G. S. Coumbarides, M. Dingjan, J. Eames, S. Ghilagaber and M. Motevalli, CrystEngComm, 2005, 7, 454
    DOI: 10.1039/B504667J

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