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Protonization mechanism of carbonyl oxygen in nucleophilic reactions of carbonyl compounds

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Conclusions

The MINDO/2 and CNDO/BW methods were used to calculate the cross section of the potential surface for intramolecular proton transfer from the nucleophilic reagent to the carbonyl oxygen atom in the tetrahedral addition product of a water molecule to formaldehyde, and it was shown that practically this reaction cannot be observed without the involvement of additional particles.

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Literature cited

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    W. P. Jencks, Catalysis in Chemistry and Enzymology, McGraw-Hill (1969).

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    M. J. S. Dewar and D. H. Lo, J. Amer. Chem. Soc.,94, 5296 (1972).

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    R. J. Boyd and M. A. Whitehead, J. Chem. Soc. Dalton Trans., 73 (1972)

  4. 4.

    K. Ya. Burshtein and Yu. I. Khurgin, Izv. Akad. Nauk SSSR, Ser. Khim., 1687 (1974).

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Additional information

Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 10, pp. 2365–2366, October, 1975.

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Burshtein, K.Y., Khurgin, Y.I. Protonization mechanism of carbonyl oxygen in nucleophilic reactions of carbonyl compounds. Russ Chem Bull 24, 2253–2254 (1975). https://doi.org/10.1007/BF00929777

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Keywords

  • Oxygen
  • Formaldehyde
  • Water Molecule
  • Carbonyl
  • Oxygen Atom