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

Alioune Fall; Mohamedou El Boukhary; Thierno Mousa Seck; Farba Bouyagui Tamboura; Ibrahima Elhadj Thiam; Aliou Hamady Barry; Mohamed Gaye; Javier Ellena

doi:doi:10.11648/j.mc.20231102.11

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

Alioune Fall, Mohamedou El Boukhary, Thierno Mousa Seck, Farba Bouyagui Tamboura, Ibrahima Elhadj Thiam, Aliou Hamady Barry, Mohamed Gaye, Javier Ellena

Published in Modern Chemistry (Volume 11, Issue 2)

Received: 11 April 2023 Accepted: 27 April 2023 Published: 10 May 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°.

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

Keywords

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

References

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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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AMA Style

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://article.sciencepublishinggroup.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

Alioune Fall

Department of Chemistry, University Cheikh Anta Diop, Dakar, Senegal
Mohamedou El Boukhary

Department of Chemistry, University Cheikh Anta Diop, Dakar, Senegal
Thierno Mousa Seck

Department of Chemistry, University Cheikh Anta Diop, Dakar, Senegal
Farba Bouyagui Tamboura

Department of Chemistry, University Cheikh Anta Diop, Dakar, Senegal
Ibrahima Elhadj Thiam

Department of Chemistry, University Cheikh Anta Diop, Dakar, Senegal
Aliou Hamady Barry

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

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

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

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APA Style

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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ACS Style

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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AMA Style

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://article.sciencepublishinggroup.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}
}

Copy | Download

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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