КФУ. Карточка публикации. Theoretical and experimental study of imine-enamine tautomerism of condensation products of propanal with 4-aminobenzoic acid in ethanol

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THEORETICAL AND EXPERIMENTAL STUDY OF IMINE-ENAMINE TAUTOMERISM OF CONDENSATION PRODUCTS OF PROPANAL WITH 4-AMINOBENZOIC ACID IN ETHANOL

Форма представления

Статьи в зарубежных журналах и сборниках

Год публикации

2017

Язык

английский

Авторы, сотрудники КФУ

Клочков Владимир Васильевич, автор

Ходов Илья Анатольевич, автор

Библиографическое описание на языке оригинала

Kalmykov P.A, Khodov I.A, Klochkov V.V, Theoretical and experimental study of imine-enamine tautomerism of condensation products of propanal with 4-aminobenzoic acid in ethanol//Russian Chemical Bulletin. - 2017. - Vol.66, Is.1. - P.70-75.

Аннотация

The tautomerism of the reaction products of propanal with 4-aminobenzoic acid in ethanol was studied by J-modulated spin-echo (JMOD) 13C NMR spectroscopy and gradient-enhanced heteronuclear (ge-2D) 1H–13C HSQC spectroscopy. The existence of imine and enamine tautomeric forms of the reduced compounds in solution was established. The tautomeric equilibrium of the condensation product of propanal with 4-aminobenzoic acid in ethanol was found to be shifted toward the imine form. Quantum chemical calculations by the density functional theory (DFT) method demonstrated that the 4-(N-propylidene)aminobenzoic acid molecule forms a stronger hydrogen bond with an ethanol solvent molecule compared to the enamine molecule, resulting in a higher stability of the ethanol adduct of azomethine compared to the adduct of enamine. ? 2017, Springer Science+Business Media, LLC.

Ключевые слова

NMR, 2D NMR, DOSY, COSY, ROESY, density, functional, theoryge-2D HSQC,hydrogenation, amination, imine-enamine tautomerism, JMOD, NMR spectroscopy, Schiff bases.

Название журнала

Russian Chemical Bulletin

URL

https://www.scopus.com/inward/record.uri?eid=2-s2.0-85021631646&doi=10.1007%2fs11172-017-1701-3&partnerID=40&md5=4f650c6b855bd70d2f38e37bb283d9e4

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https://repository.kpfu.ru/?p_id=162665

Полная запись метаданных

Поле DC	Значение	Язык
dc.contributor.author	Клочков Владимир Васильевич	ru_RU
dc.contributor.author	Клочков Владимир Васильевич	ru_RU
dc.contributor.author	Ходов Илья Анатольевич	ru_RU
dc.date.accessioned	2017-01-01T00:00:00Z	ru_RU
dc.date.available	2017-01-01T00:00:00Z	ru_RU
dc.date.issued	2017	ru_RU
dc.identifier.citation	Kalmykov P.A, Khodov I.A, Klochkov V.V, Theoretical and experimental study of imine-enamine tautomerism of condensation products of propanal with 4-aminobenzoic acid in ethanol//Russian Chemical Bulletin. - 2017. - Vol.66, Is.1. - P.70-75.	ru_RU
dc.identifier.uri	https://repository.kpfu.ru/?p_id=162665	ru_RU
dc.description.abstract	Russian Chemical Bulletin	ru_RU
dc.description.abstract	The tautomerism of the reaction products of propanal with 4-aminobenzoic acid in ethanol was studied by J-modulated spin-echo (JMOD) 13C NMR spectroscopy and gradient-enhanced heteronuclear (ge-2D) 1H–13C HSQC spectroscopy. The existence of imine and enamine tautomeric forms of the reduced compounds in solution was established. The tautomeric equilibrium of the condensation product of propanal with 4-aminobenzoic acid in ethanol was found to be shifted toward the imine form. Quantum chemical calculations by the density functional theory (DFT) method demonstrated that the 4-(N-propylidene)aminobenzoic acid molecule forms a stronger hydrogen bond with an ethanol solvent molecule compared to the enamine molecule, resulting in a higher stability of the ethanol adduct of azomethine compared to the adduct of enamine. ? 2017, Springer Science+Business Media, LLC.	ru_RU
dc.language.iso	ru	ru_RU
dc.subject	NMR	ru_RU
dc.subject	2D NMR	ru_RU
dc.subject	DOSY	ru_RU
dc.subject	COSY	ru_RU
dc.subject	ROESY	ru_RU
dc.subject	density	ru_RU
dc.subject	functional	ru_RU
dc.subject	theoryge-2D HSQC	ru_RU
dc.subject	hydrogenation	ru_RU
dc.subject	amination	ru_RU
dc.subject	imine-enamine tautomerism	ru_RU
dc.subject	JMOD	ru_RU
dc.subject	NMR spectroscopy	ru_RU
dc.subject	Schiff bases.	ru_RU
dc.title	Theoretical and experimental study of imine-enamine tautomerism of condensation products of propanal with 4-aminobenzoic acid in ethanol	ru_RU
dc.type	Статьи в зарубежных журналах и сборниках	ru_RU