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Equilibrium CH-acidity of carbamoylmethylphosphoryl compounds in dimethyl sulfoxide

  • Organic Chemistry
  • Published:
Bulletin of the Academy of Sciences of the USSR, Division of chemical science Aims and scope

Conclusions

  1. 1.

    The equilibrium CH-acidity of carbamoylmethylphosphoryl compounds (CMP) relative to 9-phenylfluorene was determined by the indicator method in DMSO (K+ counterion).

  2. 2

    A linear correlation has been established between the pK values of CMP with theσCH2 constants of the substituents at the central C atom. TheσCH2 constants were calculated for the (t-Bu)2P(O), (cyclo-Hex)2P(O), Ph(EtO)P(O) and C(O)NEt2 groups.

  3. 3.

    Analysis of the dependences of the pK of CMP and other previously studied phosphoryl-substituted CH-acids on ∑σP of the substituents at the P atom shows that for all compounds, except for those containing an Ar2P(O) group, there is a single linear dependence. Compounds with two aryl groups at the P atom show a different dependence.

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Authors and Affiliations

  1. A. N. Nesmeyanov Institute of Heteroorganic Compounds, Academy of Sciences of the USSR, Moscow

    A. G. Matveeva, M. I. Terekhova, N. P. Nesterova, É. S. Petrov, E. I. Matrosov & M. I. Kabachnik

  2. L. Ya. Karpov Physicochemical Institute, Moscow

    A. G. Matveeva, M. I. Terekhova, N. P. Nesterova, É. S. Petrov, E. I. Matrosov & M. I. Kabachnik

Authors
  1. A. G. Matveeva
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  2. M. I. Terekhova
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  3. N. P. Nesterova
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  4. É. S. Petrov
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  5. E. I. Matrosov
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  6. M. I. Kabachnik
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2067–2074, September, 1988.

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Matveeva, A.G., Terekhova, M.I., Nesterova, N.P. et al. Equilibrium CH-acidity of carbamoylmethylphosphoryl compounds in dimethyl sulfoxide. Russ Chem Bull 37, 1853–1859 (1988). https://doi.org/10.1007/BF00962502

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  • DOI: https://doi.org/10.1007/BF00962502

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