Analysis of Steric Conditions by NMR. The Environment Around Phosphorus in Some of Its Esters

  • Victor Mark
Part of the Developments in Applied Spectroscopy book series (DAIS, volume 5)


Tri-tert-butyl phosphite and its derivatives and the analogous ethyl esters were characterized by NMR spectroscopy. Tri-tert-butyl phosphite proper, unlike the derivatives, did not show consistent shielding of phosphorus. Hybrid structures between triethyl and tritert-butyl phosphite were synthesized and analyzed. Analysis of the data showed a quantitative relationship between chemical shift and composition. A decrease in bond angle of trivalent phosphorus results in greater shielding of the phosphorus nucleus, and an increase results in deshielding.


Bond Angle Alkyl Substituent Triethyl Phosphite Acetone Cyanohydrin Trivalent Phosphorus 
These keywords were added by machine and not by the authors. This process is experimental and the keywords may be updated as the learning algorithm improves.


Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.


  1. 1.
    V. Mark and J. R. van Wazer, J. Org. Chem. 29: 1006 (1964).CrossRefGoogle Scholar
  2. 2.
    J.G. Verkade and R.W. King, J. Inorg. Nucl. Chem. 1:1948 (1962) and subsequent publications.Google Scholar
  3. 3.
    C.M. Blackburn, J. S. Cohen, and L. Todd, Tetrahedron Letters, 2873 (1964).Google Scholar
  4. 4.
    R.C. Fort and P. von R. Schleyer, Chem. Rev. 64: 277 (1964).CrossRefGoogle Scholar
  5. 5.
    B. L. Laube, G. Casedy, and J. G. Verkade, Abstracts of Papers Presented at the 150th Meeting of the American Chemical Society(September, 1965 ), p. 14–0.Google Scholar
  6. 6.
    N. Muller, P.C. Lauterbur, and J. Goldenson, J. Am. Chem. Soc. 78: 3557 (1958).CrossRefGoogle Scholar
  7. 7.
    J. R. Parks, J. Am Chem. Soc. 79: 757 (1959).CrossRefGoogle Scholar
  8. 8.
    C.F. C allia, J. R. van Wazer, J.N. Shoolery, and W. A. Anderson, J. Am. Chem. Soc. 79: 2719 (1959).Google Scholar
  9. 9.
    K. Irgolic, R. A. Zingaro, and M. Kudchacker, Inorg. Chem. 4: 1421 (1965).CrossRefGoogle Scholar
  10. 10.
    H. A. Bent, Chem. Rev. 61: 275 (1961).CrossRefGoogle Scholar

Copyright information

© Chicago Section of the Society for Applied Spectroscopy 1966

Authors and Affiliations

  • Victor Mark
    • 1
  1. 1.Hooker Chemical CorporationNiagara FallsUSA

Personalised recommendations