Synthesis of (<I>E</I>)-1-benzyl-4-benzylidenepyrrolidine-2, 3-dione: Spectroscopic Characterization and X-ray Structure Determination

Mouhamadou Fofana; Mohamet Diop; Cheikh Ndoye; Grégory Excoffier; Mohamed Gaye

doi:doi:10.11648/j.sjc.20231103.11

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Synthesis of (E)-1-benzyl-4-benzylidenepyrrolidine-2, 3-dione: Spectroscopic Characterization and X-ray Structure Determination

Mouhamadou Fofana, Mohamet Diop, Cheikh Ndoye, Grégory Excoffier, Mohamed Gaye

Published in Science Journal of Chemistry (Volume 11, Issue 3)

Received: 4 May 2023 Accepted: 18 May 2023 Published: 29 May 2023

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Abstract

The compound (E)-1-benzyl-4-benzylidenepyrrolidine-2,3-dione was synthetized using Ethyl 1-benzyl-4,5-dioxopyrrolidine-3-carboxylate, and benzaldehyde in Ethanol/HCl medium. The isolated compound was characterized by elemental analyses, ¹H and ¹³C NMR and FTIR spectroscopy. Suitable crystal for X-ray diffraction was obtained from slow evaporation of a solution of the compound in ethyl acetate. The compound crystallizes in the centrosymmetric space group P-1 of the triclinic system with the following unit cell parameters a = 6.4367 (4) Å, b = 7.4998 (5) Å, c = 15.3455 (5) Å,  = 86.448 (4)°, β = 78.732 (4)°,  = 83.943 (5)°, V = 721.80 (7) Å³, Z = 2, R₁ = 0.049 and wR₂ = 0.135. In the title molecule, C₁₈H₁₅NO₂, the pyrrolidine-2,3-dione ring is almost planar (r.m.s. deviation = 0.0081 Å). The pyrrolidine ring has an envelope conformation with a methylene carbon as the flap. The two phenyl rings are severely twisted with dihedral angle of 72.234 (5)°. The pyrrolidine ring is quite coplanar with the C13-C18 phenyl ring and severely twisted from the C1-C6 phenyl ring with dihedral angles of 0.762 (5)° and 72.750 (5)°. The molecule adopts an E configuration with respect to the ethylenic moiety. Unclassical C—H•••O hydrogen bonding link the molecules, forming layers in the bc plane.

Published in	Science Journal of Chemistry (Volume 11, Issue 3)
DOI	10.11648/j.sjc.20231103.11
Page(s)	71-77
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

Pyrrolidine, Benzaldehyde, FTIR, NMR, Crystal, X-ray Diffraction

References

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APA Style

Mouhamadou Fofana, Mohamet Diop, Cheikh Ndoye, Grégory Excoffier, Mohamed Gaye. (2023). Synthesis of (E)-1-benzyl-4-benzylidenepyrrolidine-2, 3-dione: Spectroscopic Characterization and X-ray Structure Determination. Science Journal of Chemistry, 11(3), 71-77. https://doi.org/10.11648/j.sjc.20231103.11

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ACS Style

Mouhamadou Fofana; Mohamet Diop; Cheikh Ndoye; Grégory Excoffier; Mohamed Gaye. Synthesis of (E)-1-benzyl-4-benzylidenepyrrolidine-2, 3-dione: Spectroscopic Characterization and X-ray Structure Determination. Sci. J. Chem. 2023, 11(3), 71-77. doi: 10.11648/j.sjc.20231103.11

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AMA Style

Mouhamadou Fofana, Mohamet Diop, Cheikh Ndoye, Grégory Excoffier, Mohamed Gaye. Synthesis of (E)-1-benzyl-4-benzylidenepyrrolidine-2, 3-dione: Spectroscopic Characterization and X-ray Structure Determination. Sci J Chem. 2023;11(3):71-77. doi: 10.11648/j.sjc.20231103.11

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@article{10.11648/j.sjc.20231103.11,
  author = {Mouhamadou Fofana and Mohamet Diop and Cheikh Ndoye and Grégory Excoffier and Mohamed Gaye},
  title = {Synthesis of (E)-1-benzyl-4-benzylidenepyrrolidine-2, 3-dione: Spectroscopic Characterization and X-ray Structure Determination},
  journal = {Science Journal of Chemistry},
  volume = {11},
  number = {3},
  pages = {71-77},
  doi = {10.11648/j.sjc.20231103.11},
  url = {https://doi.org/10.11648/j.sjc.20231103.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20231103.11},
  abstract = {The compound (E)-1-benzyl-4-benzylidenepyrrolidine-2,3-dione was synthetized using Ethyl 1-benzyl-4,5-dioxopyrrolidine-3-carboxylate, and benzaldehyde in Ethanol/HCl medium. The isolated compound was characterized by elemental analyses, 1H and 13C NMR and FTIR spectroscopy. Suitable crystal for X-ray diffraction was obtained from slow evaporation of a solution of the compound in ethyl acetate. The compound crystallizes in the centrosymmetric space group P-1 of the triclinic system with the following unit cell parameters a = 6.4367 (4) Å, b = 7.4998 (5) Å, c = 15.3455 (5) Å,  = 86.448 (4)°, β = 78.732 (4)°,  = 83.943 (5)°, V = 721.80 (7) Å3, Z = 2, R1 = 0.049 and wR2 = 0.135. In the title molecule, C18H15NO2, the pyrrolidine-2,3-dione ring is almost planar (r.m.s. deviation = 0.0081 Å). The pyrrolidine ring has an envelope conformation with a methylene carbon as the flap. The two phenyl rings are severely twisted with dihedral angle of 72.234 (5)°. The pyrrolidine ring is quite coplanar with the C13-C18 phenyl ring and severely twisted from the C1-C6 phenyl ring with dihedral angles of 0.762 (5)° and 72.750 (5)°. The molecule adopts an E configuration with respect to the ethylenic moiety. Unclassical C—H•••O hydrogen bonding link the molecules, forming layers in the bc plane.},
 year = {2023}
}

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TY  - JOUR
T1  - Synthesis of (E)-1-benzyl-4-benzylidenepyrrolidine-2, 3-dione: Spectroscopic Characterization and X-ray Structure Determination
AU  - Mouhamadou Fofana
AU  - Mohamet Diop
AU  - Cheikh Ndoye
AU  - Grégory Excoffier
AU  - Mohamed Gaye
Y1  - 2023/05/29
PY  - 2023
N1  - https://doi.org/10.11648/j.sjc.20231103.11
DO  - 10.11648/j.sjc.20231103.11
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 71
EP  - 77
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20231103.11
AB  - The compound (E)-1-benzyl-4-benzylidenepyrrolidine-2,3-dione was synthetized using Ethyl 1-benzyl-4,5-dioxopyrrolidine-3-carboxylate, and benzaldehyde in Ethanol/HCl medium. The isolated compound was characterized by elemental analyses, 1H and 13C NMR and FTIR spectroscopy. Suitable crystal for X-ray diffraction was obtained from slow evaporation of a solution of the compound in ethyl acetate. The compound crystallizes in the centrosymmetric space group P-1 of the triclinic system with the following unit cell parameters a = 6.4367 (4) Å, b = 7.4998 (5) Å, c = 15.3455 (5) Å,  = 86.448 (4)°, β = 78.732 (4)°,  = 83.943 (5)°, V = 721.80 (7) Å3, Z = 2, R1 = 0.049 and wR2 = 0.135. In the title molecule, C18H15NO2, the pyrrolidine-2,3-dione ring is almost planar (r.m.s. deviation = 0.0081 Å). The pyrrolidine ring has an envelope conformation with a methylene carbon as the flap. The two phenyl rings are severely twisted with dihedral angle of 72.234 (5)°. The pyrrolidine ring is quite coplanar with the C13-C18 phenyl ring and severely twisted from the C1-C6 phenyl ring with dihedral angles of 0.762 (5)° and 72.750 (5)°. The molecule adopts an E configuration with respect to the ethylenic moiety. Unclassical C—H•••O hydrogen bonding link the molecules, forming layers in the bc plane.
VL  - 11
IS  - 3
ER  -

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Author Information

Mouhamadou Fofana

Department of Chemistry, University Cheikh Anta Diop, Dakar, Senegal
Mohamet Diop

Department of Chemistry, University Cheikh Anta Diop, Dakar, Senegal
Cheikh Ndoye

Department of Chemistry, University Cheikh Anta Diop, Dakar, Senegal
Grégory Excoffier

CNRS UMR 6263, Aix Marseille University, Marseille, France
Mohamed Gaye

Department of Chemistry, University Cheikh Anta Diop, Dakar, Senegal

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APA Style

Mouhamadou Fofana, Mohamet Diop, Cheikh Ndoye, Grégory Excoffier, Mohamed Gaye. (2023). Synthesis of (E)-1-benzyl-4-benzylidenepyrrolidine-2, 3-dione: Spectroscopic Characterization and X-ray Structure Determination. Science Journal of Chemistry, 11(3), 71-77. https://doi.org/10.11648/j.sjc.20231103.11

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ACS Style

Mouhamadou Fofana; Mohamet Diop; Cheikh Ndoye; Grégory Excoffier; Mohamed Gaye. Synthesis of (E)-1-benzyl-4-benzylidenepyrrolidine-2, 3-dione: Spectroscopic Characterization and X-ray Structure Determination. Sci. J. Chem. 2023, 11(3), 71-77. doi: 10.11648/j.sjc.20231103.11

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AMA Style

Mouhamadou Fofana, Mohamet Diop, Cheikh Ndoye, Grégory Excoffier, Mohamed Gaye. Synthesis of (E)-1-benzyl-4-benzylidenepyrrolidine-2, 3-dione: Spectroscopic Characterization and X-ray Structure Determination. Sci J Chem. 2023;11(3):71-77. doi: 10.11648/j.sjc.20231103.11

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@article{10.11648/j.sjc.20231103.11,
  author = {Mouhamadou Fofana and Mohamet Diop and Cheikh Ndoye and Grégory Excoffier and Mohamed Gaye},
  title = {Synthesis of (E)-1-benzyl-4-benzylidenepyrrolidine-2, 3-dione: Spectroscopic Characterization and X-ray Structure Determination},
  journal = {Science Journal of Chemistry},
  volume = {11},
  number = {3},
  pages = {71-77},
  doi = {10.11648/j.sjc.20231103.11},
  url = {https://doi.org/10.11648/j.sjc.20231103.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20231103.11},
  abstract = {The compound (E)-1-benzyl-4-benzylidenepyrrolidine-2,3-dione was synthetized using Ethyl 1-benzyl-4,5-dioxopyrrolidine-3-carboxylate, and benzaldehyde in Ethanol/HCl medium. The isolated compound was characterized by elemental analyses, 1H and 13C NMR and FTIR spectroscopy. Suitable crystal for X-ray diffraction was obtained from slow evaporation of a solution of the compound in ethyl acetate. The compound crystallizes in the centrosymmetric space group P-1 of the triclinic system with the following unit cell parameters a = 6.4367 (4) Å, b = 7.4998 (5) Å, c = 15.3455 (5) Å,  = 86.448 (4)°, β = 78.732 (4)°,  = 83.943 (5)°, V = 721.80 (7) Å3, Z = 2, R1 = 0.049 and wR2 = 0.135. In the title molecule, C18H15NO2, the pyrrolidine-2,3-dione ring is almost planar (r.m.s. deviation = 0.0081 Å). The pyrrolidine ring has an envelope conformation with a methylene carbon as the flap. The two phenyl rings are severely twisted with dihedral angle of 72.234 (5)°. The pyrrolidine ring is quite coplanar with the C13-C18 phenyl ring and severely twisted from the C1-C6 phenyl ring with dihedral angles of 0.762 (5)° and 72.750 (5)°. The molecule adopts an E configuration with respect to the ethylenic moiety. Unclassical C—H•••O hydrogen bonding link the molecules, forming layers in the bc plane.},
 year = {2023}
}

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TY  - JOUR
T1  - Synthesis of (E)-1-benzyl-4-benzylidenepyrrolidine-2, 3-dione: Spectroscopic Characterization and X-ray Structure Determination
AU  - Mouhamadou Fofana
AU  - Mohamet Diop
AU  - Cheikh Ndoye
AU  - Grégory Excoffier
AU  - Mohamed Gaye
Y1  - 2023/05/29
PY  - 2023
N1  - https://doi.org/10.11648/j.sjc.20231103.11
DO  - 10.11648/j.sjc.20231103.11
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 71
EP  - 77
PB  - Science Publishing Group
SN  - 2330-099X
UR  - https://doi.org/10.11648/j.sjc.20231103.11
AB  - The compound (E)-1-benzyl-4-benzylidenepyrrolidine-2,3-dione was synthetized using Ethyl 1-benzyl-4,5-dioxopyrrolidine-3-carboxylate, and benzaldehyde in Ethanol/HCl medium. The isolated compound was characterized by elemental analyses, 1H and 13C NMR and FTIR spectroscopy. Suitable crystal for X-ray diffraction was obtained from slow evaporation of a solution of the compound in ethyl acetate. The compound crystallizes in the centrosymmetric space group P-1 of the triclinic system with the following unit cell parameters a = 6.4367 (4) Å, b = 7.4998 (5) Å, c = 15.3455 (5) Å,  = 86.448 (4)°, β = 78.732 (4)°,  = 83.943 (5)°, V = 721.80 (7) Å3, Z = 2, R1 = 0.049 and wR2 = 0.135. In the title molecule, C18H15NO2, the pyrrolidine-2,3-dione ring is almost planar (r.m.s. deviation = 0.0081 Å). The pyrrolidine ring has an envelope conformation with a methylene carbon as the flap. The two phenyl rings are severely twisted with dihedral angle of 72.234 (5)°. The pyrrolidine ring is quite coplanar with the C13-C18 phenyl ring and severely twisted from the C1-C6 phenyl ring with dihedral angles of 0.762 (5)° and 72.750 (5)°. The molecule adopts an E configuration with respect to the ethylenic moiety. Unclassical C—H•••O hydrogen bonding link the molecules, forming layers in the bc plane.
VL  - 11
IS  - 3
ER  -

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