کد مقاله کد نشریه سال انتشار مقاله انگلیسی نسخه تمام متن
1408472 1501741 2014 9 صفحه PDF دانلود رایگان
عنوان انگلیسی مقاله ISI
Synthesis, characterization and computational study on ethyl 4-(3-Furan-2yl-acryloyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate
موضوعات مرتبط
مهندسی و علوم پایه شیمی شیمی آلی
پیش نمایش صفحه اول مقاله
Synthesis, characterization and computational study on ethyl 4-(3-Furan-2yl-acryloyl)-3,5-dimethyl-1H-pyrrole-2-carboxylate
چکیده انگلیسی


• UV–visible spectrum studied using TD-DFT/6-31G(d,p) method indicates n–π* and π–π* transitions.
• FT-IR spectrum study indicates dimer formation.
• Vibrational analysis shows red shifts in νNH and νCO as result of dimer formation.
• Binding energy of dimer is calculated as 13.82 kcal/mol.
• Descriptors analyses indicate that chalcone CCCO frame is prone to attack leading to formation of heterocyclic compounds.

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, 1H 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 NH···O and CH···O. The vibrational analysis shows red shifts in νNH and νCO 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 β-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.

Figure optionsDownload as PowerPoint slide

ناشر
Database: Elsevier - ScienceDirect (ساینس دایرکت)
Journal: Journal of Molecular Structure - Volume 1076, 5 November 2014, Pages 437–445
نویسندگان
, , ,