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Synthesis of N'-(2,3-dihydroxybenzylidene)-4-methylbenzohydrazide: Spectroscopic Characterization and X-ray Structure Determination

Received: Apr. 11, 2023    Accepted: Apr. 27, 2023    Published: May 10, 2023
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Abstract

p-Toluic hydrazide was used for synthetizing a new Schiff base N'-(2,3-dihydroxybenzylidene)-4-methylbenzohydrazide (I). The prepared compound was characterized by elemental analysis, infrared and 1H and 13C NMR spectroscopy techniques, and the structure of compound (I) was determined by single-crystal X-ray diffraction study. The compound (C15H14N2O3) crystallises in the monoclinic space group P21/n with the following unit cell parameters: a = 11.7820 (6) Å, b = 8.5278 (4) Å, c = 13.6054 (7) Å, β = 109.346 (5)°, V = 1289.81 (12) Å3, Z = 4, R1 = 0.071 and wR2 = 0.197. The X-ray structure shows that the compound (I) adopts an E configuration with respect to the double bond C7=N1. The carbonyl oxygen atom O3 and the nitrogen atom N1 of the hydrazide moiety are in a syn conformation with respect to C8—N2 bond. The crystal packing of compound (I) is stabilized by intramolecular O(phenol)–H•••N(carbohydrazide) which results in an S(6) ring motif and intermolecular O(phenol)–H•••O(carbohydrazide) hydrogen bonds which form chains. The carbonohydrazide moiety C=N–N–C(O)–N–N=C fragment is almost coplanar with the two benzene rings with dihedral angles of their mean planes of 10.35° [C1—C6] and 7.99° [C9—C14], respectively. The dihedral angle between the mean planes of the phenyl rings is 2.46°.

DOI 10.11648/j.mc.20231102.11
Published in Modern Chemistry ( Volume 11, Issue 2, June 2023 )
Page(s) 43-48
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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

Schiff Base, 2,3-dihroxybenzaldehyde, p-toluic Hydrazide, Single Crystal Structure

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    Alioune Fall, Mohamedou El Boukhary, Thierno Mousa Seck, Farba Bouyagui Tamboura, Ibrahima Elhadj Thiam, et al. (2023). Synthesis of N'-(2,3-dihydroxybenzylidene)-4-methylbenzohydrazide: Spectroscopic Characterization and X-ray Structure Determination. Modern Chemistry, 11(2), 43-48. https://doi.org/10.11648/j.mc.20231102.11

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    Alioune Fall; Mohamedou El Boukhary; Thierno Mousa Seck; Farba Bouyagui Tamboura; Ibrahima Elhadj Thiam, et al. Synthesis of N'-(2,3-dihydroxybenzylidene)-4-methylbenzohydrazide: Spectroscopic Characterization and X-ray Structure Determination. Mod. Chem. 2023, 11(2), 43-48. doi: 10.11648/j.mc.20231102.11

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    Alioune Fall, Mohamedou El Boukhary, Thierno Mousa Seck, Farba Bouyagui Tamboura, Ibrahima Elhadj Thiam, et al. Synthesis of N'-(2,3-dihydroxybenzylidene)-4-methylbenzohydrazide: Spectroscopic Characterization and X-ray Structure Determination. Mod Chem. 2023;11(2):43-48. doi: 10.11648/j.mc.20231102.11

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  • @article{10.11648/j.mc.20231102.11,
      author = {Alioune Fall and Mohamedou El Boukhary and Thierno Mousa Seck and Farba Bouyagui Tamboura and Ibrahima Elhadj Thiam and Aliou Hamady Barry and Mohamed Gaye and Javier Ellena},
      title = {Synthesis of N'-(2,3-dihydroxybenzylidene)-4-methylbenzohydrazide: Spectroscopic Characterization and X-ray Structure Determination},
      journal = {Modern Chemistry},
      volume = {11},
      number = {2},
      pages = {43-48},
      doi = {10.11648/j.mc.20231102.11},
      url = {https://doi.org/10.11648/j.mc.20231102.11},
      eprint = {https://download.sciencepg.com/pdf/10.11648.j.mc.20231102.11},
      abstract = {p-Toluic hydrazide was used for synthetizing a new Schiff base N'-(2,3-dihydroxybenzylidene)-4-methylbenzohydrazide (I). The prepared compound was characterized by elemental analysis, infrared and 1H and 13C NMR spectroscopy techniques, and the structure of compound (I) was determined by single-crystal X-ray diffraction study. The compound (C15H14N2O3) crystallises in the monoclinic space group P21/n with the following unit cell parameters: a = 11.7820 (6) Å, b = 8.5278 (4) Å, c = 13.6054 (7) Å, β = 109.346 (5)°, V = 1289.81 (12) Å3, Z = 4, R1 = 0.071 and wR2 = 0.197. The X-ray structure shows that the compound (I) adopts an E configuration with respect to the double bond C7=N1. The carbonyl oxygen atom O3 and the nitrogen atom N1 of the hydrazide moiety are in a syn conformation with respect to C8—N2 bond. The crystal packing of compound (I) is stabilized by intramolecular O(phenol)–H•••N(carbohydrazide) which results in an S(6) ring motif and intermolecular O(phenol)–H•••O(carbohydrazide) hydrogen bonds which form chains. The carbonohydrazide moiety C=N–N–C(O)–N–N=C fragment is almost coplanar with the two benzene rings with dihedral angles of their mean planes of 10.35° [C1—C6] and 7.99° [C9—C14], respectively. The dihedral angle between the mean planes of the phenyl rings is 2.46°.},
     year = {2023}
    }
    

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  • TY  - JOUR
    T1  - Synthesis of N'-(2,3-dihydroxybenzylidene)-4-methylbenzohydrazide: Spectroscopic Characterization and X-ray Structure Determination
    AU  - Alioune Fall
    AU  - Mohamedou El Boukhary
    AU  - Thierno Mousa Seck
    AU  - Farba Bouyagui Tamboura
    AU  - Ibrahima Elhadj Thiam
    AU  - Aliou Hamady Barry
    AU  - Mohamed Gaye
    AU  - Javier Ellena
    Y1  - 2023/05/10
    PY  - 2023
    N1  - https://doi.org/10.11648/j.mc.20231102.11
    DO  - 10.11648/j.mc.20231102.11
    T2  - Modern Chemistry
    JF  - Modern Chemistry
    JO  - Modern Chemistry
    SP  - 43
    EP  - 48
    PB  - Science Publishing Group
    SN  - 2329-180X
    UR  - https://doi.org/10.11648/j.mc.20231102.11
    AB  - p-Toluic hydrazide was used for synthetizing a new Schiff base N'-(2,3-dihydroxybenzylidene)-4-methylbenzohydrazide (I). The prepared compound was characterized by elemental analysis, infrared and 1H and 13C NMR spectroscopy techniques, and the structure of compound (I) was determined by single-crystal X-ray diffraction study. The compound (C15H14N2O3) crystallises in the monoclinic space group P21/n with the following unit cell parameters: a = 11.7820 (6) Å, b = 8.5278 (4) Å, c = 13.6054 (7) Å, β = 109.346 (5)°, V = 1289.81 (12) Å3, Z = 4, R1 = 0.071 and wR2 = 0.197. The X-ray structure shows that the compound (I) adopts an E configuration with respect to the double bond C7=N1. The carbonyl oxygen atom O3 and the nitrogen atom N1 of the hydrazide moiety are in a syn conformation with respect to C8—N2 bond. The crystal packing of compound (I) is stabilized by intramolecular O(phenol)–H•••N(carbohydrazide) which results in an S(6) ring motif and intermolecular O(phenol)–H•••O(carbohydrazide) hydrogen bonds which form chains. The carbonohydrazide moiety C=N–N–C(O)–N–N=C fragment is almost coplanar with the two benzene rings with dihedral angles of their mean planes of 10.35° [C1—C6] and 7.99° [C9—C14], respectively. The dihedral angle between the mean planes of the phenyl rings is 2.46°.
    VL  - 11
    IS  - 2
    ER  - 

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Author Information
  • Department of Chemistry, University Cheikh Anta Diop, Dakar, Senegal

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

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

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

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

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

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

  • Instituto de Fisica, Universidade de Sao Paulo, Sao Paulo, Brazilia

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