Theoretical study of the association of aryl derivatives of lactic acid

D.P. Gerasimova, L.V. Frantsuzova, R.R. Fayzullin, O.A. Lodochnikova

Arbuzov Institute of Organic and Physical Chemistry, FRC Kazan Scientific Center,

Russian Academy of Sciences, Kazan, 420088 Russia

E-mail: *darya.p_gerasimova@mail.ru, **lubovfrancuzova48@mail.ru,

***robert.fayzullin@gmail.com, ****lod_olga@mail.ru

Received December 23, 2022; Accepted February 13, 2023

 

ORIGINAL ARTICLE

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DOI: 10.26907/2542-064X.2023.1.49-57

For citation: Gerasimova D.P., Frantsuzova L.V., Fayzullin R.R., Lodochnikova O.A. Theoretical study of the association of aryl derivatives of lactic acid. Uchenye Zapiski Kazanskogo Universiteta. Seriya Estestvennye Nauki, 2023, vol. 165, no. 1, pp. 49–57. doi: 10.26907/2542-064X.2023.1.49-57. (In Russian)

 

Abstract

A theoretical study of the association of phenyl and ortho-substituted aryl derivatives of lactic acid was carried out. Two variants of hydrogen-bonded associates in the gas phase were calculated: non-classical, actually found in the crystals, and simulated classical dimers. The energy advantage of classical dimers and the non-equivalence of diastereotopic electron lone pairs at the carbonyl oxygen atom were shown.

Keywords: hydrogen-bonded dimer, carboxylic acids, electron lone pairs

Acknowledgements. This study was supported by the Russian Science Foundation (project no. 22-13-00284).

Figure Captions

Scheme 1. Structural formulas of the studied compounds.

Scheme 2. General layout of a) non-classical (actual) and b) classical (simulated) dimers.

Scheme 3. pro-E and pro-Z stereodescriptors of diastereotopic atoms and electron lone pairs.

Fig. 1. a) Classical dimers of compounds 1–3 illustrated by the example of compound 1; b) classical dimer of compound 4.

Fig. 2. a) Non-classical dimer of compound 1; b) non-classical dimer of compound 2; c) non-classical dimer of compounds 3 and 4 illustrated by the example of compound 3.

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