Syntheses, Antioxidant Activity and Crystal Structures of 1-Nicotinoyl-4-Phenylthiosemicarbazide and Its Derivative <I>N</I>-Phenyl-5-(Pyridin-3-yl)-1,3,4-Oxadiazol-2-amine

Ndama Faye; Aissatou Alioune Gaye; Alioune Fall; Cheikh Ndoye; Mayoro Diop; Gregory Excoffier; Mohamed Gaye

doi:doi:10.11648/j.mc.20221004.12

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Syntheses, Antioxidant Activity and Crystal Structures of 1-Nicotinoyl-4-Phenylthiosemicarbazide and Its Derivative N-Phenyl-5-(Pyridin-3-yl)-1,3,4-Oxadiazol-2-amine

Ndama Faye, Aissatou Alioune Gaye, Alioune Fall, Cheikh Ndoye, Mayoro Diop, Gregory Excoffier, Mohamed Gaye

Published in Modern Chemistry (Volume 10, Issue 4)

Received: 23 November 2022 Accepted: 7 December 2022 Published: 15 December 2022

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Abstract

The title compound C₁₃H₁₂N₄OS (I) is synthetized from nicotinic hydrazide and isothiocynate. Compound C₁₃H₁₀N₄O (II) is obtained upon reaction of (I) with Mn (II) salt. Compound I crystallizes in the triclinic space group Pī with the following unit cell parameters: a = 9.5667 (2) Å, b = 11.5464 (2) Å, c = 12.6658 (2) Å, a = 78.320 (1)°, b = 83.319 (1)°, g = 88.079 (2)°, V = 1360.73 (4) Å³, Z = 4, R₁ = 0.040 and wR₂ = 0.112 and compound II crystallizes in the monoclinic space group P2₁/n with the following unit cell parameters: a = 5.4055 (2) Å, b = 19.686 (1) Å, c = 10.5015 (4) Å, b = 92.402 (2)°, V = 1116.51 (8) Å³, Z = 4, R₁ = 0.070 and wR₂ = 0.212. The asymmetric unit contains two molecules of I. For both molecules, the carbonyl oxygen atom and the sulfur atom are, respectively, in syn and trans conformation with respect to their related amino nitrogen atoms. Strong intermolecular bonds of type N—H···N, N—H···S, and N—H···O, and weak intermolecular bonds of type C—H···O and C—H···S form chains superimposed on each other which are linked, resulting in a three-dimensional network architecture. The heterocyclic compound (II) 1,3,4-oxadiazol derivative is not planar with dihedral angle of 17.725 (14)° and 4.550 (15)° between 1,3,4-oxadiazole ring and phenyl and pyridine rings respectively. The dihedral angle between the phenyl and pyridine rings is 22.260 (12)°. In the compound II, intramolecular hydrogen bonds of type C—H···N resulting in S(6) ring stabilize the structure. One intermolecular hydrogen bonds of type N—H···N links the molecules thus forming a chain parallel to the c-axis.

Published in	Modern Chemistry (Volume 10, Issue 4)
DOI	10.11648/j.mc.20221004.12
Page(s)	113-120
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), 2022. Published by Science Publishing Group

Keywords

Phenyl Isothiocyanate, Thiosemicarbazide, Hydrazide, Oxadiazole, Antioxidant, Activity

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Ndama Faye, Aissatou Alioune Gaye, Alioune Fall, Cheikh Ndoye, Mayoro Diop, et al. (2022). Syntheses, Antioxidant Activity and Crystal Structures of 1-Nicotinoyl-4-Phenylthiosemicarbazide and Its Derivative N-Phenyl-5-(Pyridin-3-yl)-1,3,4-Oxadiazol-2-amine. Modern Chemistry, 10(4), 113-120. https://doi.org/10.11648/j.mc.20221004.12

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Ndama Faye; Aissatou Alioune Gaye; Alioune Fall; Cheikh Ndoye; Mayoro Diop, et al. Syntheses, Antioxidant Activity and Crystal Structures of 1-Nicotinoyl-4-Phenylthiosemicarbazide and Its Derivative N-Phenyl-5-(Pyridin-3-yl)-1,3,4-Oxadiazol-2-amine. Mod. Chem. 2022, 10(4), 113-120. doi: 10.11648/j.mc.20221004.12

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Ndama Faye, Aissatou Alioune Gaye, Alioune Fall, Cheikh Ndoye, Mayoro Diop, et al. Syntheses, Antioxidant Activity and Crystal Structures of 1-Nicotinoyl-4-Phenylthiosemicarbazide and Its Derivative N-Phenyl-5-(Pyridin-3-yl)-1,3,4-Oxadiazol-2-amine. Mod Chem. 2022;10(4):113-120. doi: 10.11648/j.mc.20221004.12

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@article{10.11648/j.mc.20221004.12,
  author = {Ndama Faye and Aissatou Alioune Gaye and Alioune Fall and Cheikh Ndoye and Mayoro Diop and Gregory Excoffier and Mohamed Gaye},
  title = {Syntheses, Antioxidant Activity and Crystal Structures of 1-Nicotinoyl-4-Phenylthiosemicarbazide and Its Derivative N-Phenyl-5-(Pyridin-3-yl)-1,3,4-Oxadiazol-2-amine},
  journal = {Modern Chemistry},
  volume = {10},
  number = {4},
  pages = {113-120},
  doi = {10.11648/j.mc.20221004.12},
  url = {https://doi.org/10.11648/j.mc.20221004.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20221004.12},
  abstract = {The title compound C13H12N4OS (I) is synthetized from nicotinic hydrazide and isothiocynate. Compound C13H10N4O (II) is obtained upon reaction of (I) with Mn (II) salt. Compound I crystallizes in the triclinic space group Pī with the following unit cell parameters: a = 9.5667 (2) Å, b = 11.5464 (2) Å, c = 12.6658 (2) Å, a = 78.320 (1)°, b = 83.319 (1)°, g = 88.079 (2)°, V = 1360.73 (4) Å3, Z = 4, R1 = 0.040 and wR2 = 0.112 and compound II crystallizes in the monoclinic space group P21/n with the following unit cell parameters: a = 5.4055 (2) Å, b = 19.686 (1) Å, c = 10.5015 (4) Å, b = 92.402 (2)°, V = 1116.51 (8) Å3, Z = 4, R1 = 0.070 and wR2 = 0.212. The asymmetric unit contains two molecules of I. For both molecules, the carbonyl oxygen atom and the sulfur atom are, respectively, in syn and trans conformation with respect to their related amino nitrogen atoms. Strong intermolecular bonds of type N—H···N, N—H···S, and N—H···O, and weak intermolecular bonds of type C—H···O and C—H···S form chains superimposed on each other which are linked, resulting in a three-dimensional network architecture. The heterocyclic compound (II) 1,3,4-oxadiazol derivative is not planar with dihedral angle of 17.725 (14)° and 4.550 (15)° between 1,3,4-oxadiazole ring and phenyl and pyridine rings respectively. The dihedral angle between the phenyl and pyridine rings is 22.260 (12)°. In the compound II, intramolecular hydrogen bonds of type C—H···N resulting in S(6) ring stabilize the structure. One intermolecular hydrogen bonds of type N—H···N links the molecules thus forming a chain parallel to the c-axis.},
 year = {2022}
}

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TY  - JOUR
T1  - Syntheses, Antioxidant Activity and Crystal Structures of 1-Nicotinoyl-4-Phenylthiosemicarbazide and Its Derivative N-Phenyl-5-(Pyridin-3-yl)-1,3,4-Oxadiazol-2-amine
AU  - Ndama Faye
AU  - Aissatou Alioune Gaye
AU  - Alioune Fall
AU  - Cheikh Ndoye
AU  - Mayoro Diop
AU  - Gregory Excoffier
AU  - Mohamed Gaye
Y1  - 2022/12/15
PY  - 2022
N1  - https://doi.org/10.11648/j.mc.20221004.12
DO  - 10.11648/j.mc.20221004.12
T2  - Modern Chemistry
JF  - Modern Chemistry
JO  - Modern Chemistry
SP  - 113
EP  - 120
PB  - Science Publishing Group
SN  - 2329-180X
UR  - https://doi.org/10.11648/j.mc.20221004.12
AB  - The title compound C13H12N4OS (I) is synthetized from nicotinic hydrazide and isothiocynate. Compound C13H10N4O (II) is obtained upon reaction of (I) with Mn (II) salt. Compound I crystallizes in the triclinic space group Pī with the following unit cell parameters: a = 9.5667 (2) Å, b = 11.5464 (2) Å, c = 12.6658 (2) Å, a = 78.320 (1)°, b = 83.319 (1)°, g = 88.079 (2)°, V = 1360.73 (4) Å3, Z = 4, R1 = 0.040 and wR2 = 0.112 and compound II crystallizes in the monoclinic space group P21/n with the following unit cell parameters: a = 5.4055 (2) Å, b = 19.686 (1) Å, c = 10.5015 (4) Å, b = 92.402 (2)°, V = 1116.51 (8) Å3, Z = 4, R1 = 0.070 and wR2 = 0.212. The asymmetric unit contains two molecules of I. For both molecules, the carbonyl oxygen atom and the sulfur atom are, respectively, in syn and trans conformation with respect to their related amino nitrogen atoms. Strong intermolecular bonds of type N—H···N, N—H···S, and N—H···O, and weak intermolecular bonds of type C—H···O and C—H···S form chains superimposed on each other which are linked, resulting in a three-dimensional network architecture. The heterocyclic compound (II) 1,3,4-oxadiazol derivative is not planar with dihedral angle of 17.725 (14)° and 4.550 (15)° between 1,3,4-oxadiazole ring and phenyl and pyridine rings respectively. The dihedral angle between the phenyl and pyridine rings is 22.260 (12)°. In the compound II, intramolecular hydrogen bonds of type C—H···N resulting in S(6) ring stabilize the structure. One intermolecular hydrogen bonds of type N—H···N links the molecules thus forming a chain parallel to the c-axis.
VL  - 10
IS  - 4
ER  -

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Ndama Faye

Department of Chemistry, University Cheikh Anta Diop, Dakar, Sénégal
Aissatou Alioune Gaye

Department of Chemistry, University Cheikh Anta Diop, Dakar, Sénégal
Alioune Fall

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

Department of Chemistry, University Cheikh Anta Diop, Dakar, Sénégal
Mayoro Diop

Department of Chemistry, University Cheikh Anta Diop, Dakar, Sénégal
Gregory Excoffier

Spectropole, Aix Marseille Université, Marseille, France
Mohamed Gaye

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

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APA Style

Ndama Faye, Aissatou Alioune Gaye, Alioune Fall, Cheikh Ndoye, Mayoro Diop, et al. (2022). Syntheses, Antioxidant Activity and Crystal Structures of 1-Nicotinoyl-4-Phenylthiosemicarbazide and Its Derivative N-Phenyl-5-(Pyridin-3-yl)-1,3,4-Oxadiazol-2-amine. Modern Chemistry, 10(4), 113-120. https://doi.org/10.11648/j.mc.20221004.12

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ACS Style

Ndama Faye; Aissatou Alioune Gaye; Alioune Fall; Cheikh Ndoye; Mayoro Diop, et al. Syntheses, Antioxidant Activity and Crystal Structures of 1-Nicotinoyl-4-Phenylthiosemicarbazide and Its Derivative N-Phenyl-5-(Pyridin-3-yl)-1,3,4-Oxadiazol-2-amine. Mod. Chem. 2022, 10(4), 113-120. doi: 10.11648/j.mc.20221004.12

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AMA Style

Ndama Faye, Aissatou Alioune Gaye, Alioune Fall, Cheikh Ndoye, Mayoro Diop, et al. Syntheses, Antioxidant Activity and Crystal Structures of 1-Nicotinoyl-4-Phenylthiosemicarbazide and Its Derivative N-Phenyl-5-(Pyridin-3-yl)-1,3,4-Oxadiazol-2-amine. Mod Chem. 2022;10(4):113-120. doi: 10.11648/j.mc.20221004.12

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@article{10.11648/j.mc.20221004.12,
  author = {Ndama Faye and Aissatou Alioune Gaye and Alioune Fall and Cheikh Ndoye and Mayoro Diop and Gregory Excoffier and Mohamed Gaye},
  title = {Syntheses, Antioxidant Activity and Crystal Structures of 1-Nicotinoyl-4-Phenylthiosemicarbazide and Its Derivative N-Phenyl-5-(Pyridin-3-yl)-1,3,4-Oxadiazol-2-amine},
  journal = {Modern Chemistry},
  volume = {10},
  number = {4},
  pages = {113-120},
  doi = {10.11648/j.mc.20221004.12},
  url = {https://doi.org/10.11648/j.mc.20221004.12},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.mc.20221004.12},
  abstract = {The title compound C13H12N4OS (I) is synthetized from nicotinic hydrazide and isothiocynate. Compound C13H10N4O (II) is obtained upon reaction of (I) with Mn (II) salt. Compound I crystallizes in the triclinic space group Pī with the following unit cell parameters: a = 9.5667 (2) Å, b = 11.5464 (2) Å, c = 12.6658 (2) Å, a = 78.320 (1)°, b = 83.319 (1)°, g = 88.079 (2)°, V = 1360.73 (4) Å3, Z = 4, R1 = 0.040 and wR2 = 0.112 and compound II crystallizes in the monoclinic space group P21/n with the following unit cell parameters: a = 5.4055 (2) Å, b = 19.686 (1) Å, c = 10.5015 (4) Å, b = 92.402 (2)°, V = 1116.51 (8) Å3, Z = 4, R1 = 0.070 and wR2 = 0.212. The asymmetric unit contains two molecules of I. For both molecules, the carbonyl oxygen atom and the sulfur atom are, respectively, in syn and trans conformation with respect to their related amino nitrogen atoms. Strong intermolecular bonds of type N—H···N, N—H···S, and N—H···O, and weak intermolecular bonds of type C—H···O and C—H···S form chains superimposed on each other which are linked, resulting in a three-dimensional network architecture. The heterocyclic compound (II) 1,3,4-oxadiazol derivative is not planar with dihedral angle of 17.725 (14)° and 4.550 (15)° between 1,3,4-oxadiazole ring and phenyl and pyridine rings respectively. The dihedral angle between the phenyl and pyridine rings is 22.260 (12)°. In the compound II, intramolecular hydrogen bonds of type C—H···N resulting in S(6) ring stabilize the structure. One intermolecular hydrogen bonds of type N—H···N links the molecules thus forming a chain parallel to the c-axis.},
 year = {2022}
}

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TY  - JOUR
T1  - Syntheses, Antioxidant Activity and Crystal Structures of 1-Nicotinoyl-4-Phenylthiosemicarbazide and Its Derivative N-Phenyl-5-(Pyridin-3-yl)-1,3,4-Oxadiazol-2-amine
AU  - Ndama Faye
AU  - Aissatou Alioune Gaye
AU  - Alioune Fall
AU  - Cheikh Ndoye
AU  - Mayoro Diop
AU  - Gregory Excoffier
AU  - Mohamed Gaye
Y1  - 2022/12/15
PY  - 2022
N1  - https://doi.org/10.11648/j.mc.20221004.12
DO  - 10.11648/j.mc.20221004.12
T2  - Modern Chemistry
JF  - Modern Chemistry
JO  - Modern Chemistry
SP  - 113
EP  - 120
PB  - Science Publishing Group
SN  - 2329-180X
UR  - https://doi.org/10.11648/j.mc.20221004.12
AB  - The title compound C13H12N4OS (I) is synthetized from nicotinic hydrazide and isothiocynate. Compound C13H10N4O (II) is obtained upon reaction of (I) with Mn (II) salt. Compound I crystallizes in the triclinic space group Pī with the following unit cell parameters: a = 9.5667 (2) Å, b = 11.5464 (2) Å, c = 12.6658 (2) Å, a = 78.320 (1)°, b = 83.319 (1)°, g = 88.079 (2)°, V = 1360.73 (4) Å3, Z = 4, R1 = 0.040 and wR2 = 0.112 and compound II crystallizes in the monoclinic space group P21/n with the following unit cell parameters: a = 5.4055 (2) Å, b = 19.686 (1) Å, c = 10.5015 (4) Å, b = 92.402 (2)°, V = 1116.51 (8) Å3, Z = 4, R1 = 0.070 and wR2 = 0.212. The asymmetric unit contains two molecules of I. For both molecules, the carbonyl oxygen atom and the sulfur atom are, respectively, in syn and trans conformation with respect to their related amino nitrogen atoms. Strong intermolecular bonds of type N—H···N, N—H···S, and N—H···O, and weak intermolecular bonds of type C—H···O and C—H···S form chains superimposed on each other which are linked, resulting in a three-dimensional network architecture. The heterocyclic compound (II) 1,3,4-oxadiazol derivative is not planar with dihedral angle of 17.725 (14)° and 4.550 (15)° between 1,3,4-oxadiazole ring and phenyl and pyridine rings respectively. The dihedral angle between the phenyl and pyridine rings is 22.260 (12)°. In the compound II, intramolecular hydrogen bonds of type C—H···N resulting in S(6) ring stabilize the structure. One intermolecular hydrogen bonds of type N—H···N links the molecules thus forming a chain parallel to the c-axis.
VL  - 10
IS  - 4
ER  -

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