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HERO ID
4581561
Reference Type
Journal Article
Title
Synthesis, characterization and computational study on ethyl 4-(3-Furan-2yl-acryloyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate
Author(s)
Singh, RN; Rawat, P; Sahu, S
Year
2014
Is Peer Reviewed?
Yes
Journal
Journal of Molecular Structure
ISSN:
0022-2860
EISSN:
1872-8014
Volume
1076
Page Numbers
437-445
DOI
10.1016/j.molstruc.2014.07.074
Web of Science Id
WOS:000343613400055
Abstract
As part of study on pyrrole derivatives, we have synthesized a pyrrole chalcone derivative: ethyl 4-(3-Furan-2yl-acryloyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate (EFADPC) by aldol condensation of ethyl 3, 5-dimethyl-4-actyl-1H-pyrrole-2-carboxylate with furan-2-carbaldehyde in the presence of strong hydroxyl base as catalyst. The product EFADPC has been confirmed by spectroscopic (FT-IR, H-1 NMR, and UV-visible) analyses. Quantum chemical calculation also provides good correlation with experimental data. The molecular electrostatic potential surface (MEP), natural bond orbital interactions (NBO), electronic descriptors, quantum theory of atoms' in molecules (QTAIM) and experimental FT-IR spectrum have been used to predict the sites and nature of interactions which indicate that the dimer formation with multiple interactions through N-H center dot center dot center dot O and C-H center dot center dot center dot O. The vibrational analysis shows red shifts in VN-H and V-C=O as result of dimer formation. The binding energy of dimer is calculated as 13.82, 15.24 kcal/mol using DFT, QTAIM analysis, respectively. The result of ellipticity confirms the existence of resonance assisted hydrogen bonds (RAHB) in dimer. The MEP and local reactivity descriptors analyses have been performed and the results indicate that carbonyl carbon and beta-carbon of chalcone frame have been prone to nucleophilic attack and lead to large number of heterocyclic compounds such as oxirane, oxazoles, pyrazoles, pyridines, pyrimidines, and pyran. (C) 2014 Elsevier B.V. All rights reserved.
Keywords
Chalcones; Vibrational study; Electronic descriptors; QTAIM; MEP
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