Abstract
A series of conformationally heterogeneous and energetically multilevel ω-diphenylphosphoryl- and ω-diphenylthiophosphoryl-substituted aliphatic alcohols, whose molecules are capable of five-, six-, and seven-membered ring closure due to the OH...O=P or OH...S=P intramolecular hydrogen bond (IHB), was studied by IR spectroscopy and molecular mechanics. The data obtained confirm the previous assumption that the energy of IHB (E IHB) differs substantially from the difference of enthalpies of conformers with and without IHB (–ΔH ), which is experimentally determined by the temperature dependence of the intensity of IR ν(OH) absorption bands. The measured –ΔH values can be positive, zero, or negative at significant IHB effects, i.e., at high Δν(OH) and E IHB values.
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Shagidullin, R.R., Chernova, A.V., Katsyuba, S.A. et al. Energetics of intramolecular hydrogen bonds and conformations of ω-diphenylphosphoryl- and ω-diphenylthiophosphoryl-substituted aliphatic alcohol molecules. Russian Chemical Bulletin 53, 55–59 (2004). https://doi.org/10.1023/B:RUCB.0000024829.54293.33
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DOI: https://doi.org/10.1023/B:RUCB.0000024829.54293.33