Solvatochromism of heteroaromatic compounds: XXXI. Energetics of hydrogen bonding between N-methyltrifluoromethanesulfonamide and ethers

For a series of H-complexes of ethers with N-methyltrifluoromethanesulfonamide CF3SO2NHMe, a proportionality between the spectral shift (ΔvNH) and the enthalpy of complex formation (ΔH) was found. Comparison with hydroxyl-containing H-bond donors revealed the following contradiction: ΔH increases in...

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Bibliographic Details
Published in:Russian journal of general chemistry 2007-02, Vol.77 (2), p.264-273
Main Authors: Sterkhova, I. V., Vokin, A. I., Oznobikhina, L. P., Chipanina, N. N., Shainyan, B. A., Turchaninov, V. K.
Format: Article
Language:English
Subjects:
Complex formation
Enthalpy
Ethers
Heterocyclic compounds
Hydrogen bonding
Hydrogen bonds
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Summary:For a series of H-complexes of ethers with N-methyltrifluoromethanesulfonamide CF3SO2NHMe, a proportionality between the spectral shift (ΔvNH) and the enthalpy of complex formation (ΔH) was found. Comparison with hydroxyl-containing H-bond donors revealed the following contradiction: ΔH increases in the order CF3SO2NHMe < MeOH < PhOH, whereas ΔvXH increases in the order MeOH < CF3SO2NHMe ∼ PhOH. The absence of a single Badger-Bauer relationship ΔvXH ∼ f(ΔH) is due to the contribution of universal interactions into the enthalpy of H-complex formation. The account for these interactions allowed calculation of the energy of an intermolecular hydrogen bond, which varies in parallel with the spectral shift: MeOH < CF3SO2NHMe ∼ PhOH.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363207020120