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Hydrogen Bonding in Alkyl Phosphonic and Alkyl Phosphonothionic Acids

Naturevolume 192pages12831284 (1961) | Download Citation



IN a recent series of papers1, Peppard et al. have examined alkyl and aryl phosphoric and phosphonic acids and their esters. As a result of cryoscopic and infra-red measurements, they have concluded that, except in acetic acid solution, organophosphorus acids are dimeric, or polymeric, depending on the solvent, and that there is no evidence of the monomer in dilute solutions (M/1,000) in carbon tetrachloride. They conclude that the hydrogen bonding in these acids is stronger than that in carboxylic acids. These conclusions are in agreement with those reached by earlier workers2–5, who all report the bonding to be unaffected by dilution in non-polar solvents. In view of these findings, it has been suggested3,6 that the hydrogen bonding may be intramolecular.

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  1. 1

    Peppard, D. F., Ferraro, J. R., and Mason, G. W., J. Inorg. Nucl. Chem., 4, 371 (1957).; 7, 231 (1958); 12, 60 (1959); 16, 246 (1960).

  2. 2

    Bellamy, L. J., Infrared Spectra of Complex Molecules, second ed. (Methuen, London, 1959).

  3. 3

    Maarsen, J. W., thesis, University of Amsterdam (1956).

  4. 4

    Jones, R. N., and Sandorfy, Camille, “The Application of Infrared and Raman Spectrometry to the Elucidation of Molecular Structure”; Part 4 of Weissberger's Chemical Applications of Spectroscopy (Intersci. Pub., London, 1956).

  5. 5

    Freedman, L. W., and Doak, G. O., Chem. Rev., 57 (3), 479 (1957).

  6. 6

    Thomas, L. C., Chem. and Indust., 198 (1957).

  7. 7

    Corbridge, D. E. C., J. App. Chem., 6, 456 (1956).

  8. 8

    Ryskin, Ya. I., and Stavitskaya, G. P., Optics and Spectroscopy, 7, 488 (1959).

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  1. Chemical Defence Experimental Establishment (War Department), Porton Down, Wilts

    • L. C. THOMAS
    •  & H. E. R. HARTLEY


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