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Dipole moments and structure of ortho-diphenyl(diethyl)phosphinoyl-substituted benzyl alcohols, phenols, and their derivatives

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Abstract

The method of dipole moments and DFT B3LYP/6-31G* quantum-chemical calculations were used to study the structures of ortho-substituted aryl-and arylmethyldiphenyl(diethyl)phosphine oxides. It was established that methyl ethers of phosphorus-containing benzyl alcohols and phenols exist as equilibrium mixtures of several conformers with prevalence of forms with the weakest steric interactions. Preferred conformers of o-[(diethylphosphinoyl)methyl]benzyl alcohol and i-[(diphenylphosphinoyl)methyl]phenol contain an intramolecular hydrogen bond between the hydroxyl hydrogen atom and phosphinoyl oxygen atom.

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Authors and Affiliations

  1. Kazan State University, ul. Kremlevskaya 18, Kazan, 420008, Russia

    E. A. Ishmaeva & Ya. A. Vereshcjhagina

  2. Kazan State Technological University, Kazan, Russia

    A. A. Gazizova & Ya. A. Vereshcjhagina

  3. Scientific Research Institute of Chemical Reagents and Ultrapure Chemical Substances (FGUP IREA), Moscow, Russia

    N. A. Bondarenko

Authors
  1. E. A. Ishmaeva
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  2. A. A. Gazizova
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  3. Ya. A. Vereshcjhagina
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  4. N. A. Bondarenko
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Correspondence to E. A. Ishmaeva.

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Original Russian Text © E.A. Ishmaeva, A.A. Gazizova, Ya.A. Vereshcjhagina, N.A. Bondarenko, 2008, published in Zhurnal Obshchei Khimii, 2008, Vol. 78, No. 9, pp. 1429–1434.

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Ishmaeva, E.A., Gazizova, A.A., Vereshcjhagina, Y.A. et al. Dipole moments and structure of ortho-diphenyl(diethyl)phosphinoyl-substituted benzyl alcohols, phenols, and their derivatives. Russ J Gen Chem 78, 1662–1667 (2008). https://doi.org/10.1134/S1070363208090041

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  • DOI: https://doi.org/10.1134/S1070363208090041

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