Conclusions
-
1.
The acid-base properties of the phosphine oxides were studied by the method of potentiometric titration in nitromethane. The titration curve has two potential jumps at the points of 50% and 100% neutralization, which is due to the formation of complexes of the BHB+ type at the first stages of protonation.
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2.
A linear correlation was obtained between the values of pK a (CH3NO2) and the σσϕ constants of the substituents at the phosphorus atom, which permitted a calculation of the σϕ constants of the -CH2OR and -CH2COOH groups.
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3.
Aminomethylphosphine oxides are titrated as nitrogen bases. Substantial differences in the values of pK a (CH3+NO2) of different degrees of protonation of the molecules of these compounds are probably due to the formation of intramolecular hydrogen bonds (of the type N+-H ... N) and the inductive effect of the protonated dialkylaminomethyl group.
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Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 6, pp. 1333–1337, June, 1975.
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Matrosov, E.I., Tsvetkov, E.N., Mironova, Z.N. et al. Acid-base properties of phosphine oxides in nitromethane. Russ Chem Bull 24, 1231–1234 (1975). https://doi.org/10.1007/BF00922052
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DOI: https://doi.org/10.1007/BF00922052