Structure of N,N-Dialkylamides of Diphenylphosphorylacetic Acid in Solution: Dipole Moments, IR Spectroscopy, and Quantum-Chemical Study

Conformational analysis of N , N -dialkylamides of diphenylphosphorylacetic acid has been carried out using the methods of dipole moments, IR spectroscopy, and quantum chemistry DFT B3PW91/6-311++G(df,p), including the CPCM model. In solution, N , N -diethyl-, N , N -dibutyl- and N , N -dioctylamide...

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Bibliographic Details
Published in:Russian journal of general chemistry 2024-02, Vol.94 (2), p.352-362
Main Authors: Kuznetsova, A. A., Chachkov, D. V., Tcarkova, K. V., Bondarenko, N. A., Vereshchagina, Ya. A.
Format: Article
Language:English
Subjects:
Carbonyl groups
Carbonyls
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
Conformational analysis
Conjugation
Dipole moments
Infrared spectroscopy
Quantum chemistry
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Summary:Conformational analysis of N , N -dialkylamides of diphenylphosphorylacetic acid has been carried out using the methods of dipole moments, IR spectroscopy, and quantum chemistry DFT B3PW91/6-311++G(df,p), including the CPCM model. In solution, N , N -diethyl-, N , N -dibutyl- and N , N -dioctylamides exist as equilibrium mixture of conformers, in which forms with cis -orientation of phenyl rings and synclinal orientation of the C sp 3‒C sp 2 (C=O) bond relative to the phosphoryl group predominate, the carbonyl group and P‒C sp 3 bond being anticlinal. The stabilization of the preferred conformers is facilitated by intramolecular hydrogen contacts and the possible presence of the p ,π-conjugation between the phosphoryl group and the phenyl ring in their molecules.
ISSN:1070-3632
1608-3350
DOI:10.1134/S1070363224020117