Stereoelectronic structure of α-bromoalkenyl trifluoromethyl ketones View Full Text


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Article Info

DATE

2009-10

AUTHORS

N. N. Chipanina, T. N. Aksamentova, A. Yu. Rulev

ABSTRACT

The results of quantum-chemical calculations at the B3LYP/6-311G** level of theory showed that (Z)-α-bromo-β-arylalkenyl trifluoromethyl ketones are more stable than the corresponding E isomers by 4–5 kcal/mol. Relatively large positive charge on the olefinic β-carbon atom and strong polarization of the C=C bond in both Z-s-cis and Z-s-trans conformers makes bromoalkenyl trifluoromethyl ketones the most potent Michael acceptors among α,β-unsaturated carbonyl compounds. The calculated data are very consistent with the experimental IR spectra. More... »

PAGES

1431

Identifiers

URI

http://scigraph.springernature.com/pub.10.1134/s1070428009100017

DOI

http://dx.doi.org/10.1134/s1070428009100017

DIMENSIONS

https://app.dimensions.ai/details/publication/pub.1026094331


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