Synthesis of Schiff Bases Compounds from Oxamic Hydrazide: Spectroscopic Characterization, X–ray Diffraction Structure and Antioxidant Activity Study

Fatou Faye; Amadou Guèye; Papa Samba Camara; Aïssatou Alioune Gaye; Farba Bouyagui Tamboura; Nathalie Gruber; Mohamed Gaye

doi:doi:10.11648/j.ajac.20210901.12

Synthesis of Schiff Bases Compounds from Oxamic Hydrazide: Spectroscopic Characterization, X–ray Diffraction Structure and Antioxidant Activity Study

Fatou Faye, Amadou Guèye, Papa Samba Camara, Aïssatou Alioune Gaye, Farba Bouyagui Tamboura, Nathalie Gruber, Mohamed Gaye

Published in American Journal of Applied Chemistry (Volume 9, Issue 1)

Received: 2 January 2021 Accepted: 11 January 2021 Published: 22 January 2021

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Abstract

The compounds (E)–2–amino–N'–(1–(2–hydroxyphenyl)ethylidene)–2–oxoacetohydrazide (I) and (E)–N'–(2–hydroxy–3–methoxybenzylidene)–2–amino–2–oxoacetohydrazide (II) were synthetized by the 1:1 ratio condensation reaction of oxamic hydrazide and 2–hydroxyacetophenone or o–vanillin respectively. The two compounds were characterized by physico–chemical analyses, elemental analysis, FTIR, ¹H and ¹³C NMR spectroscopies techniques. The structure of the compound (I) was determined by single–crystal X–ray diffraction study. The compound (I) (C₁₀H₁₁N₃O₃) crystallises in the triclinic space group P–1 with the following unit cell parameters: a = 7.0399 (5) Å, b = 8.6252 (8) Å, c = 9.5474 (9) Å, a = 81.730 (3)°, b = 72.738 (3)°, g = 67.450 (3)°, V = 510.99 (8) Å³, Z = 2, T = 173 (2) K, m = 0.11 mm^–1, D_calc = 1.438 g/cm³, R_int = 0.028, R_sigma = 0.073. The oxamic hydrazide moiety of the molecule is slightly twisted as reflected by the torsion angles values of 177.2 (2)° [N1–N2–C9–C10], –171.3 (3)° [N2–C9–C10–N3], –4.6 (4)° [O2–C9–N2–N1] and 8.4 (4)° [O3–C10–C9–N2]. The intramolecular hydrogen bond O1(phenol)–H1•••N1(hydrazide) which close in S (6) ring stabilized the conformation. The intermolecular hydrogen bonds, C3–H3•••O1ⁱ(phenol) (i: −x+1, −y, −z+1), N3(amide)–H3A•••O3ⁱⁱ(amide) (ii: −x+1, −y+2, −z) and N3(amide)–H3B•••O2ⁱⁱⁱ(hydrazide) (iii: −x+1, −y+1, −z) lead to the formation of sheets parallel to ac plane. Compounds (I) and (II) showed antioxidant activities less than 10% inhibition of DPPH.

Published in	American Journal of Applied Chemistry (Volume 9, Issue 1)
DOI	10.11648/j.ajac.20210901.12
Page(s)	6-12
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

Oxamic Hydrazide, 2–hydroxyacetophenone, O–vanillin, Antioxidant, X–ray

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Fatou Faye, Amadou Guèye, Papa Samba Camara, Aïssatou Alioune Gaye, Farba Bouyagui Tamboura, et al. (2021). Synthesis of Schiff Bases Compounds from Oxamic Hydrazide: Spectroscopic Characterization, X–ray Diffraction Structure and Antioxidant Activity Study. American Journal of Applied Chemistry, 9(1), 6-12. https://doi.org/10.11648/j.ajac.20210901.12

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Fatou Faye; Amadou Guèye; Papa Samba Camara; Aïssatou Alioune Gaye; Farba Bouyagui Tamboura, et al. Synthesis of Schiff Bases Compounds from Oxamic Hydrazide: Spectroscopic Characterization, X–ray Diffraction Structure and Antioxidant Activity Study. Am. J. Appl. Chem. 2021, 9(1), 6-12. doi: 10.11648/j.ajac.20210901.12

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Fatou Faye, Amadou Guèye, Papa Samba Camara, Aïssatou Alioune Gaye, Farba Bouyagui Tamboura, et al. Synthesis of Schiff Bases Compounds from Oxamic Hydrazide: Spectroscopic Characterization, X–ray Diffraction Structure and Antioxidant Activity Study. Am J Appl Chem. 2021;9(1):6-12. doi: 10.11648/j.ajac.20210901.12

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@article{10.11648/j.ajac.20210901.12,
  author = {Fatou Faye and Amadou Guèye and Papa Samba Camara and Aïssatou Alioune Gaye and Farba Bouyagui Tamboura and Nathalie Gruber and Mohamed Gaye},
  title = {Synthesis of Schiff Bases Compounds from Oxamic Hydrazide: Spectroscopic Characterization, X–ray Diffraction Structure and Antioxidant Activity Study},
  journal = {American Journal of Applied Chemistry},
  volume = {9},
  number = {1},
  pages = {6-12},
  doi = {10.11648/j.ajac.20210901.12},
  url = {https://doi.org/10.11648/j.ajac.20210901.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajac.20210901.12},
  abstract = {The compounds (E)–2–amino–N'–(1–(2–hydroxyphenyl)ethylidene)–2–oxoacetohydrazide (I) and (E)–N'–(2–hydroxy–3–methoxybenzylidene)–2–amino–2–oxoacetohydrazide (II) were synthetized by the 1:1 ratio condensation reaction of oxamic hydrazide and 2–hydroxyacetophenone or o–vanillin respectively. The two compounds were characterized by physico–chemical analyses, elemental analysis, FTIR, 1H and 13C NMR spectroscopies techniques. The structure of the compound (I) was determined by single–crystal X–ray diffraction study. The compound (I) (C10H11N3O3) crystallises in the triclinic space group P–1 with the following unit cell parameters: a = 7.0399 (5) Å, b = 8.6252 (8) Å, c = 9.5474 (9) Å, a = 81.730 (3)°, b = 72.738 (3)°, g = 67.450 (3)°, V = 510.99 (8) Å3, Z = 2, T = 173 (2) K, m = 0.11 mm–1, Dcalc = 1.438 g/cm3, Rint = 0.028, Rsigma = 0.073. The oxamic hydrazide moiety of the molecule is slightly twisted as reflected by the torsion angles values of 177.2 (2)° [N1–N2–C9–C10], –171.3 (3)° [N2–C9–C10–N3], –4.6 (4)° [O2–C9–N2–N1] and 8.4 (4)° [O3–C10–C9–N2]. The intramolecular hydrogen bond O1(phenol)–H1•••N1(hydrazide) which close in S (6) ring stabilized the conformation. The intermolecular hydrogen bonds, C3–H3•••O1i(phenol) (i: −x+1, −y, −z+1), N3(amide)–H3A•••O3ii(amide) (ii: −x+1, −y+2, −z) and N3(amide)–H3B•••O2iii(hydrazide) (iii: −x+1, −y+1, −z) lead to the formation of sheets parallel to ac plane. Compounds (I) and (II) showed antioxidant activities less than 10% inhibition of DPPH.},
 year = {2021}
}

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TY  - JOUR
T1  - Synthesis of Schiff Bases Compounds from Oxamic Hydrazide: Spectroscopic Characterization, X–ray Diffraction Structure and Antioxidant Activity Study
AU  - Fatou Faye
AU  - Amadou Guèye
AU  - Papa Samba Camara
AU  - Aïssatou Alioune Gaye
AU  - Farba Bouyagui Tamboura
AU  - Nathalie Gruber
AU  - Mohamed Gaye
Y1  - 2021/01/22
PY  - 2021
N1  - https://doi.org/10.11648/j.ajac.20210901.12
DO  - 10.11648/j.ajac.20210901.12
T2  - American Journal of Applied Chemistry
JF  - American Journal of Applied Chemistry
JO  - American Journal of Applied Chemistry
SP  - 6
EP  - 12
PB  - Science Publishing Group
SN  - 2330-8745
UR  - https://doi.org/10.11648/j.ajac.20210901.12
AB  - The compounds (E)–2–amino–N'–(1–(2–hydroxyphenyl)ethylidene)–2–oxoacetohydrazide (I) and (E)–N'–(2–hydroxy–3–methoxybenzylidene)–2–amino–2–oxoacetohydrazide (II) were synthetized by the 1:1 ratio condensation reaction of oxamic hydrazide and 2–hydroxyacetophenone or o–vanillin respectively. The two compounds were characterized by physico–chemical analyses, elemental analysis, FTIR, 1H and 13C NMR spectroscopies techniques. The structure of the compound (I) was determined by single–crystal X–ray diffraction study. The compound (I) (C10H11N3O3) crystallises in the triclinic space group P–1 with the following unit cell parameters: a = 7.0399 (5) Å, b = 8.6252 (8) Å, c = 9.5474 (9) Å, a = 81.730 (3)°, b = 72.738 (3)°, g = 67.450 (3)°, V = 510.99 (8) Å3, Z = 2, T = 173 (2) K, m = 0.11 mm–1, Dcalc = 1.438 g/cm3, Rint = 0.028, Rsigma = 0.073. The oxamic hydrazide moiety of the molecule is slightly twisted as reflected by the torsion angles values of 177.2 (2)° [N1–N2–C9–C10], –171.3 (3)° [N2–C9–C10–N3], –4.6 (4)° [O2–C9–N2–N1] and 8.4 (4)° [O3–C10–C9–N2]. The intramolecular hydrogen bond O1(phenol)–H1•••N1(hydrazide) which close in S (6) ring stabilized the conformation. The intermolecular hydrogen bonds, C3–H3•••O1i(phenol) (i: −x+1, −y, −z+1), N3(amide)–H3A•••O3ii(amide) (ii: −x+1, −y+2, −z) and N3(amide)–H3B•••O2iii(hydrazide) (iii: −x+1, −y+1, −z) lead to the formation of sheets parallel to ac plane. Compounds (I) and (II) showed antioxidant activities less than 10% inhibition of DPPH.
VL  - 9
IS  - 1
ER  -

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Author Information

Fatou Faye

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

Department of Chemistry, University Cheikh Anta Diop, Dakar, Senegal
Papa Samba Camara

Department of Chemistry, University Alioune Diop, Bambey, Senegal
Aïssatou Alioune Gaye
Farba Bouyagui Tamboura

Department of Chemistry, University Alioune Diop, Bambey, Senegal
Nathalie Gruber

Institut Le Bel, University of Strasbourg, Strasbourg, France
Mohamed Gaye

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

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Fatou Faye, Amadou Guèye, Papa Samba Camara, Aïssatou Alioune Gaye, Farba Bouyagui Tamboura, et al. (2021). Synthesis of Schiff Bases Compounds from Oxamic Hydrazide: Spectroscopic Characterization, X–ray Diffraction Structure and Antioxidant Activity Study. American Journal of Applied Chemistry, 9(1), 6-12. https://doi.org/10.11648/j.ajac.20210901.12

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Fatou Faye; Amadou Guèye; Papa Samba Camara; Aïssatou Alioune Gaye; Farba Bouyagui Tamboura, et al. Synthesis of Schiff Bases Compounds from Oxamic Hydrazide: Spectroscopic Characterization, X–ray Diffraction Structure and Antioxidant Activity Study. Am. J. Appl. Chem. 2021, 9(1), 6-12. doi: 10.11648/j.ajac.20210901.12

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AMA Style

Fatou Faye, Amadou Guèye, Papa Samba Camara, Aïssatou Alioune Gaye, Farba Bouyagui Tamboura, et al. Synthesis of Schiff Bases Compounds from Oxamic Hydrazide: Spectroscopic Characterization, X–ray Diffraction Structure and Antioxidant Activity Study. Am J Appl Chem. 2021;9(1):6-12. doi: 10.11648/j.ajac.20210901.12

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@article{10.11648/j.ajac.20210901.12,
  author = {Fatou Faye and Amadou Guèye and Papa Samba Camara and Aïssatou Alioune Gaye and Farba Bouyagui Tamboura and Nathalie Gruber and Mohamed Gaye},
  title = {Synthesis of Schiff Bases Compounds from Oxamic Hydrazide: Spectroscopic Characterization, X–ray Diffraction Structure and Antioxidant Activity Study},
  journal = {American Journal of Applied Chemistry},
  volume = {9},
  number = {1},
  pages = {6-12},
  doi = {10.11648/j.ajac.20210901.12},
  url = {https://doi.org/10.11648/j.ajac.20210901.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajac.20210901.12},
  abstract = {The compounds (E)–2–amino–N'–(1–(2–hydroxyphenyl)ethylidene)–2–oxoacetohydrazide (I) and (E)–N'–(2–hydroxy–3–methoxybenzylidene)–2–amino–2–oxoacetohydrazide (II) were synthetized by the 1:1 ratio condensation reaction of oxamic hydrazide and 2–hydroxyacetophenone or o–vanillin respectively. The two compounds were characterized by physico–chemical analyses, elemental analysis, FTIR, 1H and 13C NMR spectroscopies techniques. The structure of the compound (I) was determined by single–crystal X–ray diffraction study. The compound (I) (C10H11N3O3) crystallises in the triclinic space group P–1 with the following unit cell parameters: a = 7.0399 (5) Å, b = 8.6252 (8) Å, c = 9.5474 (9) Å, a = 81.730 (3)°, b = 72.738 (3)°, g = 67.450 (3)°, V = 510.99 (8) Å3, Z = 2, T = 173 (2) K, m = 0.11 mm–1, Dcalc = 1.438 g/cm3, Rint = 0.028, Rsigma = 0.073. The oxamic hydrazide moiety of the molecule is slightly twisted as reflected by the torsion angles values of 177.2 (2)° [N1–N2–C9–C10], –171.3 (3)° [N2–C9–C10–N3], –4.6 (4)° [O2–C9–N2–N1] and 8.4 (4)° [O3–C10–C9–N2]. The intramolecular hydrogen bond O1(phenol)–H1•••N1(hydrazide) which close in S (6) ring stabilized the conformation. The intermolecular hydrogen bonds, C3–H3•••O1i(phenol) (i: −x+1, −y, −z+1), N3(amide)–H3A•••O3ii(amide) (ii: −x+1, −y+2, −z) and N3(amide)–H3B•••O2iii(hydrazide) (iii: −x+1, −y+1, −z) lead to the formation of sheets parallel to ac plane. Compounds (I) and (II) showed antioxidant activities less than 10% inhibition of DPPH.},
 year = {2021}
}

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TY  - JOUR
T1  - Synthesis of Schiff Bases Compounds from Oxamic Hydrazide: Spectroscopic Characterization, X–ray Diffraction Structure and Antioxidant Activity Study
AU  - Fatou Faye
AU  - Amadou Guèye
AU  - Papa Samba Camara
AU  - Aïssatou Alioune Gaye
AU  - Farba Bouyagui Tamboura
AU  - Nathalie Gruber
AU  - Mohamed Gaye
Y1  - 2021/01/22
PY  - 2021
N1  - https://doi.org/10.11648/j.ajac.20210901.12
DO  - 10.11648/j.ajac.20210901.12
T2  - American Journal of Applied Chemistry
JF  - American Journal of Applied Chemistry
JO  - American Journal of Applied Chemistry
SP  - 6
EP  - 12
PB  - Science Publishing Group
SN  - 2330-8745
UR  - https://doi.org/10.11648/j.ajac.20210901.12
AB  - The compounds (E)–2–amino–N'–(1–(2–hydroxyphenyl)ethylidene)–2–oxoacetohydrazide (I) and (E)–N'–(2–hydroxy–3–methoxybenzylidene)–2–amino–2–oxoacetohydrazide (II) were synthetized by the 1:1 ratio condensation reaction of oxamic hydrazide and 2–hydroxyacetophenone or o–vanillin respectively. The two compounds were characterized by physico–chemical analyses, elemental analysis, FTIR, 1H and 13C NMR spectroscopies techniques. The structure of the compound (I) was determined by single–crystal X–ray diffraction study. The compound (I) (C10H11N3O3) crystallises in the triclinic space group P–1 with the following unit cell parameters: a = 7.0399 (5) Å, b = 8.6252 (8) Å, c = 9.5474 (9) Å, a = 81.730 (3)°, b = 72.738 (3)°, g = 67.450 (3)°, V = 510.99 (8) Å3, Z = 2, T = 173 (2) K, m = 0.11 mm–1, Dcalc = 1.438 g/cm3, Rint = 0.028, Rsigma = 0.073. The oxamic hydrazide moiety of the molecule is slightly twisted as reflected by the torsion angles values of 177.2 (2)° [N1–N2–C9–C10], –171.3 (3)° [N2–C9–C10–N3], –4.6 (4)° [O2–C9–N2–N1] and 8.4 (4)° [O3–C10–C9–N2]. The intramolecular hydrogen bond O1(phenol)–H1•••N1(hydrazide) which close in S (6) ring stabilized the conformation. The intermolecular hydrogen bonds, C3–H3•••O1i(phenol) (i: −x+1, −y, −z+1), N3(amide)–H3A•••O3ii(amide) (ii: −x+1, −y+2, −z) and N3(amide)–H3B•••O2iii(hydrazide) (iii: −x+1, −y+1, −z) lead to the formation of sheets parallel to ac plane. Compounds (I) and (II) showed antioxidant activities less than 10% inhibition of DPPH.
VL  - 9
IS  - 1
ER  -

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