Issue 8, 1983
From the journal:

Journal of the Chemical Society, Perkin Transactions 2

Conformational studies of α-substituted carbonyl compounds. Part 1. Conformation and electronic interaction in hetero-substituted acetones by infrared and ultraviolet spectroscopy

Sandra A. Guerrero,   Jose R. T. Barros,   Blanka Wladislaw,   Roberto Rittner  and  Paulo R. Olivato  

Abstract

νC[double bond, length half m-dash]O Frequencies and intensities and n→π* transition energies were measured for some heterosubstituted ketones (XCH2COMe : X = F, Cl, Br, I, NMe2, OMe, SMe, or SEt) and compared with the corresponding unsubstituted ketone. The stability of the gauche-conformers is discussed in terms of hyperconjugative interactions between σC – X and πC[double bond, length half m-dash]O orbitals and repulsive interactions between C[double bond, length half m-dash]O and C – X dipoles. The carbonyl frequency shifts, induced by inductive (ΔνI), field (ΔνF), and hyperconjugative effects (ΔνH), are estimated separately. A close relationship is shown to exist between the ΔνH values and the energies of the n→π* transition.

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Article information

DOI
https://doi.org/10.1039/P29830001053
Article type
Paper

J. Chem. Soc., Perkin Trans. 2, 1983, 1053-1058

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Conformational studies of α-substituted carbonyl compounds. Part 1. Conformation and electronic interaction in hetero-substituted acetones by infrared and ultraviolet spectroscopy

S. A. Guerrero, J. R. T. Barros, B. Wladislaw, R. Rittner and P. R. Olivato, J. Chem. Soc., Perkin Trans. 2, 1983, 1053 DOI: 10.1039/P29830001053

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