Conclusions
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1.
According to the data of the IR spectra, solutions of N-(p-methoxyphenyl)amidodichlorophosphate and N-phenylamidodichlorophosphate are characterized by a conformational equilibrium, whereas one steric structure is stabilized for N-(p-bromophenyl)amidodichlorophosphate and N-(p-nitrophenyl)amidodichlorophosphate.
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2.
It is suggested that forms with shielding of the PO and NH bonds and a skewed mutual arrangement of them participate in the equilibrium.
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3.
The observed changes in the displacement of the conformational equilibrium as a function of the nature of the substituents in the p-position of the benzene ring are explained by the different degree of conjugation on the nitrogen atom with the phosphorus portion of the molecule.
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Translated from Izvestiya Akademii Nauk SSSR, SeriyaKhimicheskaya, No. 11, pp. 2497–2501, November, 1973.
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Raevskii, O.A., Donskaya, Y.A. & Antokhina, L.A. IR spectra and internal rotation relative to the P-N bond of certain N-arylamidodichlorophosphates. Russ Chem Bull 22, 2438–2441 (1973). https://doi.org/10.1007/BF00926389
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DOI: https://doi.org/10.1007/BF00926389