Synthesis, Characterization, Crystal Structure and Quantum Chemical Calculations of 2-oxo-2H-chromen-3-yl Acetate

Akoun Abou; Siaka Sosso; Affiba Florance Kouassi; Thouakesseh Jeremie Zoueu; Abdoulaye Djande; Olivier Ouari

doi:doi:10.11648/j.sjc.20210902.11

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Synthesis, Characterization, Crystal Structure and Quantum Chemical Calculations of 2-oxo-2H-chromen-3-yl Acetate

Akoun Abou, Siaka Sosso, Affiba Florance Kouassi, Thouakesseh Jeremie Zoueu, Abdoulaye Djande, Olivier Ouari

Published in Science Journal of Chemistry (Volume 9, Issue 2)

Received: 14 March 2021 Accepted: 6 April 2021 Published: 16 April 2021

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Abstract

This paper is focused on a combined experimental and theoretical study of 3-substituted coumarin derivative, the 2-oxo-2H-chromen-3-yl acetate (I). The compound was synthesized by reacting chroman-2,3-dione and acetic anhydride in dried diethyl ether in the presence of dried pyridine and crystallized in the orthorhombic crystal system with Pbca space group. The lattice parameters of the structure are a=14.6770 (1), b=7.1079 (1), c=17.6767 (2) Å, α=β=γ=90° with 8 molecules per unit cell (Z=8). The compound has been characterized structurally by Spectroscopy utilizing ¹H NMR, ¹³C NMR and IR techniques and by crystallography using the X-Ray diffraction (XRD) analysis. In the crystallographic study, the positions of the atoms were determined by direct methods and refined to a final R value of 0.038 for 1768 independent reflections. The stabilization of the structure is provided by intermolecular C-H•••O hydrogen bonds extending along [010] direction. Likewise, the presence and nature of intermolecular contacts are determined by the 3-D molecular Hirshfeld surface and 2-D fingerprint plot analysis which indicate the main contributions to the Hirshfeld surface, 38.7% for O ••• H and 28.7% for H •• H. Moreover, the molecular geometry of (I) was as well minimized utilizing density functional theory (DFT/RB3LYP), the frequency calculations with RB3LYP method, the basic ab initio model i.e the restricted Hartree-Fock (RHF) and the exchange component of Perdew and Wang’s 1991 functional B3PW91 methods with the 6-311⁺⁺G(d, p) basis set in ground state. The derived structural parameters highlight very good correlation with the crystallographic results. Frontier molecular orbitals (HOMO-LUMO), their energy gap, the non-linear optical effects (NLO) and related reactive parameters were also computed to better apprehend the properties of the molecule.

Published in	Science Journal of Chemistry (Volume 9, Issue 2)
DOI	10.11648/j.sjc.20210902.11
Page(s)	29-44
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), 2021. Published by Science Publishing Group

Keywords

3-substituted Coumarin Derivative, C—H…O Hydrogen Bonds, Hirshfeld Surface Analysis, Quantum Chemical Computations, Crystal Structure

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Akoun Abou, Siaka Sosso, Affiba Florance Kouassi, Thouakesseh Jeremie Zoueu, Abdoulaye Djande, et al. (2021). Synthesis, Characterization, Crystal Structure and Quantum Chemical Calculations of 2-oxo-2H-chromen-3-yl Acetate. Science Journal of Chemistry, 9(2), 29-44. https://doi.org/10.11648/j.sjc.20210902.11

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ACS Style

Akoun Abou; Siaka Sosso; Affiba Florance Kouassi; Thouakesseh Jeremie Zoueu; Abdoulaye Djande, et al. Synthesis, Characterization, Crystal Structure and Quantum Chemical Calculations of 2-oxo-2H-chromen-3-yl Acetate. Sci. J. Chem. 2021, 9(2), 29-44. doi: 10.11648/j.sjc.20210902.11

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AMA Style

Akoun Abou, Siaka Sosso, Affiba Florance Kouassi, Thouakesseh Jeremie Zoueu, Abdoulaye Djande, et al. Synthesis, Characterization, Crystal Structure and Quantum Chemical Calculations of 2-oxo-2H-chromen-3-yl Acetate. Sci J Chem. 2021;9(2):29-44. doi: 10.11648/j.sjc.20210902.11

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@article{10.11648/j.sjc.20210902.11,
  author = {Akoun Abou and Siaka Sosso and Affiba Florance Kouassi and Thouakesseh Jeremie Zoueu and Abdoulaye Djande and Olivier Ouari},
  title = {Synthesis, Characterization, Crystal Structure and Quantum Chemical Calculations of 2-oxo-2H-chromen-3-yl Acetate},
  journal = {Science Journal of Chemistry},
  volume = {9},
  number = {2},
  pages = {29-44},
  doi = {10.11648/j.sjc.20210902.11},
  url = {https://doi.org/10.11648/j.sjc.20210902.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20210902.11},
  abstract = {This paper is focused on a combined experimental and theoretical study of 3-substituted coumarin derivative, the 2-oxo-2H-chromen-3-yl acetate (I). The compound was synthesized by reacting chroman-2,3-dione and acetic anhydride in dried diethyl ether in the presence of dried pyridine and crystallized in the orthorhombic crystal system with Pbca space group. The lattice parameters of the structure are a=14.6770 (1), b=7.1079 (1), c=17.6767 (2) Å, α=β=γ=90° with 8 molecules per unit cell (Z=8). The compound has been characterized structurally by Spectroscopy utilizing 1H NMR, 13C NMR and IR techniques and by crystallography using the X-Ray diffraction (XRD) analysis. In the crystallographic study, the positions of the atoms were determined by direct methods and refined to a final R value of 0.038 for 1768 independent reflections. The stabilization of the structure is provided by intermolecular C-H•••O hydrogen bonds extending along [010] direction. Likewise, the presence and nature of intermolecular contacts are determined by the 3-D molecular Hirshfeld surface and 2-D fingerprint plot analysis which indicate the main contributions to the Hirshfeld surface, 38.7% for O ••• H and 28.7% for H •• H. Moreover, the molecular geometry of (I) was as well minimized utilizing density functional theory (DFT/RB3LYP), the frequency calculations with RB3LYP method, the basic ab initio model i.e the restricted Hartree-Fock (RHF) and the exchange component of Perdew and Wang’s 1991 functional B3PW91 methods with the 6-311++G(d, p) basis set in ground state. The derived structural parameters highlight very good correlation with the crystallographic results. Frontier molecular orbitals (HOMO-LUMO), their energy gap, the non-linear optical effects (NLO) and related reactive parameters were also computed to better apprehend the properties of the molecule.},
 year = {2021}
}

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TY  - JOUR
T1  - Synthesis, Characterization, Crystal Structure and Quantum Chemical Calculations of 2-oxo-2H-chromen-3-yl Acetate
AU  - Akoun Abou
AU  - Siaka Sosso
AU  - Affiba Florance Kouassi
AU  - Thouakesseh Jeremie Zoueu
AU  - Abdoulaye Djande
AU  - Olivier Ouari
Y1  - 2021/04/16
PY  - 2021
N1  - https://doi.org/10.11648/j.sjc.20210902.11
DO  - 10.11648/j.sjc.20210902.11
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 29
EP  - 44
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20210902.11
AB  - This paper is focused on a combined experimental and theoretical study of 3-substituted coumarin derivative, the 2-oxo-2H-chromen-3-yl acetate (I). The compound was synthesized by reacting chroman-2,3-dione and acetic anhydride in dried diethyl ether in the presence of dried pyridine and crystallized in the orthorhombic crystal system with Pbca space group. The lattice parameters of the structure are a=14.6770 (1), b=7.1079 (1), c=17.6767 (2) Å, α=β=γ=90° with 8 molecules per unit cell (Z=8). The compound has been characterized structurally by Spectroscopy utilizing 1H NMR, 13C NMR and IR techniques and by crystallography using the X-Ray diffraction (XRD) analysis. In the crystallographic study, the positions of the atoms were determined by direct methods and refined to a final R value of 0.038 for 1768 independent reflections. The stabilization of the structure is provided by intermolecular C-H•••O hydrogen bonds extending along [010] direction. Likewise, the presence and nature of intermolecular contacts are determined by the 3-D molecular Hirshfeld surface and 2-D fingerprint plot analysis which indicate the main contributions to the Hirshfeld surface, 38.7% for O ••• H and 28.7% for H •• H. Moreover, the molecular geometry of (I) was as well minimized utilizing density functional theory (DFT/RB3LYP), the frequency calculations with RB3LYP method, the basic ab initio model i.e the restricted Hartree-Fock (RHF) and the exchange component of Perdew and Wang’s 1991 functional B3PW91 methods with the 6-311++G(d, p) basis set in ground state. The derived structural parameters highlight very good correlation with the crystallographic results. Frontier molecular orbitals (HOMO-LUMO), their energy gap, the non-linear optical effects (NLO) and related reactive parameters were also computed to better apprehend the properties of the molecule.
VL  - 9
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
Siaka Sosso

Department of Chemistry, Laboratory of Molecular Chemistry and Materials, Research Team: Organic Chemistry and Phytochemistry, University Joseph KI-ZERBO, Ouagadougou, Burkina Faso
Affiba Florance Kouassi

Department of Physics, Laboratory of Fundamental and Applied Physics, University of Abobo Adjamé—Nangui Abrogoua, Abidjan, C?te d’Ivoire
Thouakesseh Jeremie Zoueu

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 Djande

Department of Chemistry, Laboratory of Molecular Chemistry and Materials, Research Team: Organic Chemistry and Phytochemistry, University Joseph KI-ZERBO, Ouagadougou, Burkina Faso
Olivier Ouari

Department of Chemistry, Radical Chemistry Institute, Research Team SREP, Aix-Marseille University, Marseille, France

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Akoun Abou, Siaka Sosso, Affiba Florance Kouassi, Thouakesseh Jeremie Zoueu, Abdoulaye Djande, et al. (2021). Synthesis, Characterization, Crystal Structure and Quantum Chemical Calculations of 2-oxo-2H-chromen-3-yl Acetate. Science Journal of Chemistry, 9(2), 29-44. https://doi.org/10.11648/j.sjc.20210902.11

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ACS Style

Akoun Abou; Siaka Sosso; Affiba Florance Kouassi; Thouakesseh Jeremie Zoueu; Abdoulaye Djande, et al. Synthesis, Characterization, Crystal Structure and Quantum Chemical Calculations of 2-oxo-2H-chromen-3-yl Acetate. Sci. J. Chem. 2021, 9(2), 29-44. doi: 10.11648/j.sjc.20210902.11

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AMA Style

Akoun Abou, Siaka Sosso, Affiba Florance Kouassi, Thouakesseh Jeremie Zoueu, Abdoulaye Djande, et al. Synthesis, Characterization, Crystal Structure and Quantum Chemical Calculations of 2-oxo-2H-chromen-3-yl Acetate. Sci J Chem. 2021;9(2):29-44. doi: 10.11648/j.sjc.20210902.11

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@article{10.11648/j.sjc.20210902.11,
  author = {Akoun Abou and Siaka Sosso and Affiba Florance Kouassi and Thouakesseh Jeremie Zoueu and Abdoulaye Djande and Olivier Ouari},
  title = {Synthesis, Characterization, Crystal Structure and Quantum Chemical Calculations of 2-oxo-2H-chromen-3-yl Acetate},
  journal = {Science Journal of Chemistry},
  volume = {9},
  number = {2},
  pages = {29-44},
  doi = {10.11648/j.sjc.20210902.11},
  url = {https://doi.org/10.11648/j.sjc.20210902.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20210902.11},
  abstract = {This paper is focused on a combined experimental and theoretical study of 3-substituted coumarin derivative, the 2-oxo-2H-chromen-3-yl acetate (I). The compound was synthesized by reacting chroman-2,3-dione and acetic anhydride in dried diethyl ether in the presence of dried pyridine and crystallized in the orthorhombic crystal system with Pbca space group. The lattice parameters of the structure are a=14.6770 (1), b=7.1079 (1), c=17.6767 (2) Å, α=β=γ=90° with 8 molecules per unit cell (Z=8). The compound has been characterized structurally by Spectroscopy utilizing 1H NMR, 13C NMR and IR techniques and by crystallography using the X-Ray diffraction (XRD) analysis. In the crystallographic study, the positions of the atoms were determined by direct methods and refined to a final R value of 0.038 for 1768 independent reflections. The stabilization of the structure is provided by intermolecular C-H•••O hydrogen bonds extending along [010] direction. Likewise, the presence and nature of intermolecular contacts are determined by the 3-D molecular Hirshfeld surface and 2-D fingerprint plot analysis which indicate the main contributions to the Hirshfeld surface, 38.7% for O ••• H and 28.7% for H •• H. Moreover, the molecular geometry of (I) was as well minimized utilizing density functional theory (DFT/RB3LYP), the frequency calculations with RB3LYP method, the basic ab initio model i.e the restricted Hartree-Fock (RHF) and the exchange component of Perdew and Wang’s 1991 functional B3PW91 methods with the 6-311++G(d, p) basis set in ground state. The derived structural parameters highlight very good correlation with the crystallographic results. Frontier molecular orbitals (HOMO-LUMO), their energy gap, the non-linear optical effects (NLO) and related reactive parameters were also computed to better apprehend the properties of the molecule.},
 year = {2021}
}

Copy | Download

TY  - JOUR
T1  - Synthesis, Characterization, Crystal Structure and Quantum Chemical Calculations of 2-oxo-2H-chromen-3-yl Acetate
AU  - Akoun Abou
AU  - Siaka Sosso
AU  - Affiba Florance Kouassi
AU  - Thouakesseh Jeremie Zoueu
AU  - Abdoulaye Djande
AU  - Olivier Ouari
Y1  - 2021/04/16
PY  - 2021
N1  - https://doi.org/10.11648/j.sjc.20210902.11
DO  - 10.11648/j.sjc.20210902.11
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 29
EP  - 44
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20210902.11
AB  - This paper is focused on a combined experimental and theoretical study of 3-substituted coumarin derivative, the 2-oxo-2H-chromen-3-yl acetate (I). The compound was synthesized by reacting chroman-2,3-dione and acetic anhydride in dried diethyl ether in the presence of dried pyridine and crystallized in the orthorhombic crystal system with Pbca space group. The lattice parameters of the structure are a=14.6770 (1), b=7.1079 (1), c=17.6767 (2) Å, α=β=γ=90° with 8 molecules per unit cell (Z=8). The compound has been characterized structurally by Spectroscopy utilizing 1H NMR, 13C NMR and IR techniques and by crystallography using the X-Ray diffraction (XRD) analysis. In the crystallographic study, the positions of the atoms were determined by direct methods and refined to a final R value of 0.038 for 1768 independent reflections. The stabilization of the structure is provided by intermolecular C-H•••O hydrogen bonds extending along [010] direction. Likewise, the presence and nature of intermolecular contacts are determined by the 3-D molecular Hirshfeld surface and 2-D fingerprint plot analysis which indicate the main contributions to the Hirshfeld surface, 38.7% for O ••• H and 28.7% for H •• H. Moreover, the molecular geometry of (I) was as well minimized utilizing density functional theory (DFT/RB3LYP), the frequency calculations with RB3LYP method, the basic ab initio model i.e the restricted Hartree-Fock (RHF) and the exchange component of Perdew and Wang’s 1991 functional B3PW91 methods with the 6-311++G(d, p) basis set in ground state. The derived structural parameters highlight very good correlation with the crystallographic results. Frontier molecular orbitals (HOMO-LUMO), their energy gap, the non-linear optical effects (NLO) and related reactive parameters were also computed to better apprehend the properties of the molecule.
VL  - 9
IS  - 2
ER  -

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