Experimental and Theoretical Conformational Analysis of
			Tris(4-methylphenyl)phosphine and Its Chalcogenides

Kuznetsova, Anastasiia; Ismagilova, R. R.; Чачков, Д. В.; Белогорлова, Н. А.; Малышева, С. Ф.; Vereshchagina, Ya. A.

doi:10.1134/s1070428020120088

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“…To search the possible conformations of isolated molecules of 1 – 3 , we applied the Density Functional Theory (DFT) with B3PW91 hybrid functional. This method has been successfully used to study the polarity and spatial structure of similar organophosphorus compounds with double bond phosphorus–chalcogen and aryl substituents [ 36 , 39 ]. The choice of the B3PW91 method was also based on the data [ 40 ].…”

Section: Resultsmentioning

confidence: 99%

Conformational Analysis of N-Alkyl-N-[2-(diphenylphosphoryl)ethyl]amides of Diphenylphosphorylacetic Acid: Dipole Moments, IR Spectroscopy, DFT Study

et al. 2021

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Experimental and theoretical conformational analysis of N-methyl-N-[2-(diphenylphosphoryl)ethyl]diphenylphosphorylacetamide, N-butyl-N-[2-(diphenylphosphoryl)ethyl]diphenylphosphorylacetamide, and N-octyl-N-[2-(diphenylphosphoryl)ethyl]diphenylphosphorylacetamide was carried out by the methods of dipole moments, IR spectroscopy, and Density Functional Theory (DFT) B3PW91/6-311++G(df,p) calculations. In solution, these N,N-dialkyl substituted bisphosphorylated acetamides exist as a conformational equilibrium of several forms divided into two groups—with Z- or E-configuration of the carbonyl group and alkyl substituent, and syn or anti arrangement of the phosphoryl-containing fragments relative to the amide plane. The substituents at the phosphorus atoms have eclipsed cis- or staggered gauche-orientation relative to the P=O groups, and cis orientation of the substituents is due to the presence of intramolecular H-contacts P=O...H−Cphenyl or p,π conjugation between the phosphoryl group and the phenyl ring. Preferred conformers of acetamides molecules are additionally stabilized by various intramolecular hydrogen contacts with the participation of oxygen atoms of the P=O or C=O groups and hydrogen atoms of the methylene and ethylene bridges, alkyl substituents, and phenyl rings. However, steric factors, such as a flat amide fragment, the bulky phenyl groups, and the configuration of alkyl bridges, make a significant contribution to the realization of preferred conformers.

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Section: Resultsmentioning

confidence: 99%