Synthesis, Spectrometric Characterization, X-Ray Crystallography and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Propionate

Akoun Abou; Abdoulaye Djandé; Bintou Sessouma; Rita Kakou Yao; Olivier Ouari; Adama Saba

doi:doi:10.11648/j.ajhc.20190502.13

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Synthesis, Spectrometric Characterization, X-Ray Crystallography and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Propionate

Akoun Abou, Abdoulaye Djandé, Bintou Sessouma, Rita Kakou Yao, Olivier Ouari, Adama Saba

Published in American Journal of Heterocyclic Chemistry (Volume 5, Issue 2)

Received: 17 June 2019 Accepted: 12 July 2019 Published: 24 July 2019

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Abstract

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.

Published in	American Journal of Heterocyclic Chemistry (Volume 5, Issue 2)
DOI	10.11648/j.ajhc.20190502.13
Page(s)	37-48
Creative Commons	This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.
Copyright	Copyright © The Author(s), 2019. Published by Science Publishing Group

Keywords

Coumarin Ester, Hirshfeld Surface Analysis, Quantum Chemical Calculations

References

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Akoun Abou, Abdoulaye Djandé, Bintou Sessouma, Rita Kakou Yao, Olivier Ouari, et al. (2019). Synthesis, Spectrometric Characterization, X-Ray Crystallography and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Propionate. American Journal of Heterocyclic Chemistry, 5(2), 37-48. https://doi.org/10.11648/j.ajhc.20190502.13

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ACS Style

Akoun Abou; Abdoulaye Djandé; Bintou Sessouma; Rita Kakou Yao; Olivier Ouari, et al. Synthesis, Spectrometric Characterization, X-Ray Crystallography and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Propionate. Am. J. Heterocycl. Chem. 2019, 5(2), 37-48. doi: 10.11648/j.ajhc.20190502.13

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AMA Style

Akoun Abou, Abdoulaye Djandé, Bintou Sessouma, Rita Kakou Yao, Olivier Ouari, et al. Synthesis, Spectrometric Characterization, X-Ray Crystallography and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Propionate. Am J Heterocycl Chem. 2019;5(2):37-48. doi: 10.11648/j.ajhc.20190502.13

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@article{10.11648/j.ajhc.20190502.13,
  author = {Akoun Abou and Abdoulaye Djandé and Bintou Sessouma and Rita Kakou Yao and Olivier Ouari and Adama Saba},
  title = {Synthesis, Spectrometric Characterization, X-Ray Crystallography and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Propionate},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {5},
  number = {2},
  pages = {37-48},
  doi = {10.11648/j.ajhc.20190502.13},
  url = {https://doi.org/10.11648/j.ajhc.20190502.13},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20190502.13},
  abstract = {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.},
 year = {2019}
}

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TY  - JOUR
T1  - Synthesis, Spectrometric Characterization, X-Ray Crystallography and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Propionate
AU  - Akoun Abou
AU  - Abdoulaye Djandé
AU  - Bintou Sessouma
AU  - Rita Kakou Yao
AU  - Olivier Ouari
AU  - Adama Saba
Y1  - 2019/07/24
PY  - 2019
N1  - https://doi.org/10.11648/j.ajhc.20190502.13
DO  - 10.11648/j.ajhc.20190502.13
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 37
EP  - 48
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20190502.13
AB  - 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.
VL  - 5
IS  - 2
ER  -

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Author Information

Akoun Abou

Department of Training and Research in Electrical and Electronic Engineering, Research Team: Instrumentation, Image and Spectroscopy, Félix Houphou?t-Boigny National Polytechnic Institute, Yamoussoukro, C?te 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 Houphou?t-Boigny, Abidjan, C?te 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

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APA Style

Akoun Abou, Abdoulaye Djandé, Bintou Sessouma, Rita Kakou Yao, Olivier Ouari, et al. (2019). Synthesis, Spectrometric Characterization, X-Ray Crystallography and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Propionate. American Journal of Heterocyclic Chemistry, 5(2), 37-48. https://doi.org/10.11648/j.ajhc.20190502.13

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ACS Style

Akoun Abou; Abdoulaye Djandé; Bintou Sessouma; Rita Kakou Yao; Olivier Ouari, et al. Synthesis, Spectrometric Characterization, X-Ray Crystallography and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Propionate. Am. J. Heterocycl. Chem. 2019, 5(2), 37-48. doi: 10.11648/j.ajhc.20190502.13

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AMA Style

Akoun Abou, Abdoulaye Djandé, Bintou Sessouma, Rita Kakou Yao, Olivier Ouari, et al. Synthesis, Spectrometric Characterization, X-Ray Crystallography and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Propionate. Am J Heterocycl Chem. 2019;5(2):37-48. doi: 10.11648/j.ajhc.20190502.13

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@article{10.11648/j.ajhc.20190502.13,
  author = {Akoun Abou and Abdoulaye Djandé and Bintou Sessouma and Rita Kakou Yao and Olivier Ouari and Adama Saba},
  title = {Synthesis, Spectrometric Characterization, X-Ray Crystallography and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Propionate},
  journal = {American Journal of Heterocyclic Chemistry},
  volume = {5},
  number = {2},
  pages = {37-48},
  doi = {10.11648/j.ajhc.20190502.13},
  url = {https://doi.org/10.11648/j.ajhc.20190502.13},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20190502.13},
  abstract = {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.},
 year = {2019}
}

Copy | Download

TY  - JOUR
T1  - Synthesis, Spectrometric Characterization, X-Ray Crystallography and Quantum Chemical Calculations of 2-oxo-2H-chromen-7-yl Propionate
AU  - Akoun Abou
AU  - Abdoulaye Djandé
AU  - Bintou Sessouma
AU  - Rita Kakou Yao
AU  - Olivier Ouari
AU  - Adama Saba
Y1  - 2019/07/24
PY  - 2019
N1  - https://doi.org/10.11648/j.ajhc.20190502.13
DO  - 10.11648/j.ajhc.20190502.13
T2  - American Journal of Heterocyclic Chemistry
JF  - American Journal of Heterocyclic Chemistry
JO  - American Journal of Heterocyclic Chemistry
SP  - 37
EP  - 48
PB  - Science Publishing Group
SN  - 2575-5722
UR  - https://doi.org/10.11648/j.ajhc.20190502.13
AB  - 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.
VL  - 5
IS  - 2
ER  -

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