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Conformations of α,β-unsaturated ketones: An IR spectroscopic study

 

作者: GVenkateshwarlu,   BSubrahmanyam,  

 

期刊: Proceedings of the Indian Academy of Sciences - Chemical Sciences  (Springer Available online 2008)
卷期: Volume 102, issue 1  

页码: 45-50

 

ISSN:0370-0089

 

年代: 2008

 

DOI:10.1007/BF02861570

 

出版商: Springer_India-New_Delhi

 

数据来源: Springer

 

摘要:

The conformational analyses of substituted methyl styryl ketones and phenyl styryl ketones have been carried out using IR spectroscopy. The split in the C=O bands of these compounds is attributed to the existence of two conformations, viz.s-cisands-trans, in equilibrium. The methyl styryl ketones exist predominantly in thes-transform whereas phenyl styryl ketones exist in thes-cisform. In all the ketones studied the proportion of thes-transform increases with increase in the polarity of the solvent while that of thes-cisform decreases. This shows that thes-transform is more polar than thes-cis. The field effects between the C=O and C=C groups are found to be electrostatic repulsions which play a dominant role in the determination of the relative stabilities of thes-cisands-transforms over the steric effects and the electrostatic attractions between the carbonyl oxygen and the β-carbon

 

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