Synthesis, Spectrometric Characterization, X-Ray Crystallography and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Propionate
American Journal of Heterocyclic Chemistry
Volume 5, Issue 2, June 2019, Pages: 37-48
Received: Jun. 17, 2019;
Accepted: Jul. 12, 2019;
Published: Jul. 24, 2019
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Akoun Abou, Department of Training and Research in Electrical and Electronic Engineering, Research Team: Instrumentation, Image and Spectroscopy, Félix Houphouët-Boigny National Polytechnic Institute, Yamoussoukro, Côte d’Ivoire
Abdoulaye Djandé, Department of Chemistry, Laboratory of Molecular Chemistry and Materials, University Joseph KI-ZERBO, Ouagadougou, Burkina Faso
Bintou Sessouma, Department of Chemistry, Laboratory of Molecular Chemistry and Materials, University Joseph KI-ZERBO, Ouagadougou, Burkina Faso
Rita Kakou Yao, Department of Physics, Laboratory of Crystallography and Molecular Physics, University Félix Houphouët-Boigny, Abidjan, Côte d’Ivoire
Olivier Ouari, Department of Chemistry, Radical Chemistry Institute, Aix-Marseille University, Marseille, France
Adama Saba, Department of Chemistry, Laboratory of Molecular Chemistry and Materials, University Joseph KI-ZERBO, Ouagadougou, Burkina Faso
The title compound, (I), has been solved by direct methods and refined to a final R value of 0.038 for 1835 independent reflections. In the structure, the planar [r.m.s deviation = 0.014 Å] chromen-2-one ring and the 7-propionate side chain are inclined to one another at an acute angle of 65.34(9)°. The molecules form R44 (30) tetrameric units via C—H···O interactions which extend into layers approximately parallel to the ab plane. Furthermore, the crystal structure is supported by π–π stacking interactions between neighbouring benzene and pyrone or coumarin rings [centroid–centroid distances in the range 3.6097(8)–3.6475(9)Å], as well as C–H···π interactions [H···centroid distances in the range 2.95–3.00Å]. The molecular geometry of (I) was also optimized using density functional theory (DFT/RB3LYP), RMP2 and RHF methods with the 6-311++G(d, p) basis set in ground state. The theoretical data resulting from these quantum chemical calculations are in good agreement with the observed structure, although the observed C—O—C—C torsion angle between the coumarin ring system and the 7-propionate side chain (121.49 (16)°) is somewhat lower than the DFT/RB3LYP calculated value (132.32°) and larger than the RMP2 (114.65°) and the RHF (69.19°) values. Hirshfeld surface analysis has been used to confirm and quantify the supramolecular interactions.
Rita Kakou Yao,
Synthesis, Spectrometric Characterization, X-Ray Crystallography and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Propionate, American Journal of Heterocyclic Chemistry.
Vol. 5, No. 2,
2019, pp. 37-48.
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