KFU. Card publication. 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

Form of presentation

Articles in international journals and collections

Year of publication

2017

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Authors, employees of KFU

Klochkov Vladimir Vasilevich, author

Khodov Ilya Anatolevich, author

Bibliographic description in the original language

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.

Annotation

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.

Keywords

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

The name of the journal

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

Please use this ID to quote from or refer to the card

https://repository.kpfu.ru/eng/?p_id=162665&p_lang=2

Full metadata record

Field DC	Value	Language
dc.contributor.author	Klochkov Vladimir Vasilevich	ru_RU
dc.contributor.author	Klochkov Vladimir Vasilevich	ru_RU
dc.contributor.author	Khodov Ilya Anatolevich	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/eng/?p_id=162665&p_lang=2	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	Articles in international journals and collections	ru_RU