American Journal of Heterocyclic Chemistry

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

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.

DOI 10.11648/j.ajhc.20190502.13
Published in American Journal of Heterocyclic Chemistry (Volume 5, Issue 2, June 2019)
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), 2024. Published by Science Publishing Group

Keywords

Coumarin Ester, Hirshfeld Surface Analysis, Quantum Chemical Calculations

References
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Author Information
  • 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

  • Department of Chemistry, Laboratory of Molecular Chemistry and Materials, University Joseph KI-ZERBO, Ouagadougou, Burkina Faso

  • Department of Chemistry, Laboratory of Molecular Chemistry and Materials, University Joseph KI-ZERBO, Ouagadougou, Burkina Faso

  • Department of Physics, Laboratory of Crystallography and Molecular Physics, University Félix Houphou?t-Boigny, Abidjan, C?te d’Ivoire

  • Department of Chemistry, Radical Chemistry Institute, Aix-Marseille University, Marseille, France

  • Department of Chemistry, Laboratory of Molecular Chemistry and Materials, University Joseph KI-ZERBO, Ouagadougou, Burkina Faso

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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://download.sciencepg.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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    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
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    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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