Theoretical and experimental study of imine-enamine tautomerism of condensation products of propanal with 4-aminobenzoic acid in ethanol
Publication type: Journal Article
Publication date: 2017-01-01
scimago Q3
SJR: 0.305
CiteScore: 2.8
Impact factor: —
ISSN: 10665285, 15739171
General Chemistry
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.
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13
Total citations:
13
Citations from 2024:
2
(15%)
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Kalmykov P. A. et al. 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. No. 1. pp. 70-75.
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Kalmykov P. A., Khodov I. A., Klochkov V. V., Klyuev M. 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. No. 1. pp. 70-75.
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TY - JOUR
DO - 10.1007/s11172-017-1701-3
UR - http://link.springer.com/10.1007/s11172-017-1701-3
TI - Theoretical and experimental study of imine-enamine tautomerism of condensation products of propanal with 4-aminobenzoic acid in ethanol
T2 - Russian Chemical Bulletin
AU - Kalmykov, P A
AU - Khodov, I A
AU - Klochkov, V V
AU - Klyuev, M.V.
PY - 2017
DA - 2017/01/01
PB - Springer Nature
SP - 70-75
IS - 1
VL - 66
SN - 1066-5285
SN - 1573-9171
ER -
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@article{2017_Kalmykov,
author = {P A Kalmykov and I A Khodov and V V Klochkov and M.V. Klyuev},
title = {Theoretical and experimental study of imine-enamine tautomerism of condensation products of propanal with 4-aminobenzoic acid in ethanol},
journal = {Russian Chemical Bulletin},
year = {2017},
volume = {66},
publisher = {Springer Nature},
month = {jan},
url = {http://link.springer.com/10.1007/s11172-017-1701-3},
number = {1},
pages = {70--75},
doi = {10.1007/s11172-017-1701-3}
}
Cite this
MLA
Copy
Kalmykov, P. A., et al. “Theoretical and experimental study of imine-enamine tautomerism of condensation products of propanal with 4-aminobenzoic acid in ethanol.” Russian Chemical Bulletin, vol. 66, no. 1, Jan. 2017, pp. 70-75. http://link.springer.com/10.1007/s11172-017-1701-3.
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