Conformational Analysis of Bis[N-alkyl-N-(2-diphenylphosphorylethyl)]amides of Diglycolic Acid

A. A. Kuznetsova^a (https://orcid.org/0000-0002-6736-0698), D. V. Chachkov^b (https://orcid.org/0000-0002-0073-3672), K. V. Tcarkova^{c, d} (https://orcid.org/0000-0001-8730-0521), O. I. Artyushin^e (https://orcid.org/0000-0001-6333-5973), N. A. Bondarenko^{c, d} (https://orcid.org/0000-0002-6704-6957), and Ya. A. Vereshchagina^a^,* (https://orcid.org/0000-0002-8259-8143)

^aKazan (Volga region) Federal University, Kazan, 420008 Russia

^bKazan Department of Joint Supercomputer Center of Russian Academy of Sciences – Branch of Federal State Institution “Scientific Research Institute for System Analysis of the Russian Academy of Sciences”, Kazan, 420111 Russia

^cInstitute of Chemical Reagents and High Purity Chemical Substances of National Research Centre “Kurchatov Institute”, Moscow, 107076 Russia

^dNational Research Centre “Kurchatov Institute”, Moscow, 123182 Russia

^eA.N. Nesmeyanov Institute of Organoelement Compounds of the Russian Academy of Sciences, Moscow, 119991 Russia

email: *yavereshchagina@gmail.com

Received 5 October, 2022

Abstract— The conformational analysis of bis[N-alkyl-N-(2-diphenylphosphorylethyl)]amides of diglycolic acid has been carried out using the methods of dipole moments, IR spectroscopy, and quantum-chemical DFT B3PW91/6-311++G(df,p) simulation. In solution, N,N-dimethyl-, N,N-dibutyl-, and N,N-dioctyl-substituted diamides of diglycolic acid exist as an equilibrium mixture of two groups of symmetrical or nonsymmetrical conformers, in some of which intramolecular contacts involving hydrogen atoms of the alkyl substituents and oxygen atoms of the ether bridge or carbonyl groups are possible.

Keywords: bis[N-alkyl-N-(2-diphenylphosphorylethyl)]amides of diglycolic acid, conformational analysis, dipole moments, IR spectroscopy, quantum chemical calculations

DOI: 10.1134/S1070363222120064