Synthesis, Characterization and Crystal Structure of 1-(2-benzamidophenyl)-3-benzoylthiourea Hemihydrate

Fatou Faye; Rokhaya Sylla-Gueye; Ibrahima Elhadji Thiam; James Orton; Simon Coles; Mohamed Gaye

doi:doi:10.11648/j.sjc.20200806.11

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Synthesis, Characterization and Crystal Structure of 1-(2-benzamidophenyl)-3-benzoylthiourea Hemihydrate

Fatou Faye, Rokhaya Sylla-Gueye, Ibrahima Elhadji Thiam, James Orton, Simon Coles, Mohamed Gaye

Published in Science Journal of Chemistry (Volume 8, Issue 6)

Received: 23 November 2020 Accepted: 4 December 2020 Published: 11 December 2020

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Abstract

The dissymmetric compound C₂₁H₁₇N₃O₂S.0.5H₂O obtained by a reaction of 1,2-diaminobenzene, potassium thiocyanate and benzoyl chloride in 1/1/2 ratio is characterized by elemental analyses, IR, and NMR spectroscopies. The structure is elucidated by X-ray diffraction technic. The compound crystallizes in the monoclinic system with a space group of I2. The asymmetric unit contains one hemihydrate organic molecule. The title thiourea derivative, features an almost planar, C₂N₂S (S1/N1/N2/C7/C8) moiety, with a maximum deviation from the least-squares plane of 0.0422 (3) Å. This moiety is flanked by a disubstituted and a monosubstituted phenyl rings. The dihedral angles between the thiourea and the monosubstituted phenyl ring and the thiourea and the central disubstituted phenyl ring are respectively 10.418 (7)° and 60.292 (2)°, indicating twist in the molecule. On the other arm, a phenyl ring supported by an amide function, which is linked to the central ring through the nitrogen atom, is present. The dihedral angle between this phenyl group and the central disubstituted phenyl is 76.862 (7)° showing that their mean planes are not coplanar. Intramolecular S(thiono)—H…O(water) hydrogen bonds which close in S (6) and S (7) rings consolidate the conformation. Intermolecular N(amido)—H…O(carbonyl) which form layers parallel to the ac plane stabilized the structure.

Published in	Science Journal of Chemistry (Volume 8, Issue 6)
DOI	10.11648/j.sjc.20200806.11
Page(s)	131-135
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

1,2-diaminobenzene, Benzoyl Chloride, Potassium Thiocyanate

References

[1]	S. Karakuş, Ş. G. Küçükgüzel, İ. Küçükgüzel, E. D. Clercq, C. Pannecouque, G. Andrei, R. Snoeck, F. Şahin, Ö. F. Bayrak, Synthesis, antiviral and anticancer activity of some novel thioureas derived from N-(4-nitro-2-phenoxyphenyl)-methanesulfonamide, European Journal of Medicinal Chemistry (2009), 44, 3591–3595.
[2]	N. A. Mohamed, N. Y. Al-mehbad, Novel terephthaloyl thiourea cross-linked chitosan hydrogels as antibacterial and antifungal agents, International Journal of Biological Macromolecules (2013), 57, 111–117.
[3]	S. Y. Abbas, M. A. M. S. El-Sharief, W. M. Basyouni, I. M. I. Fakhr, E. W. El-Gammal, Thiourea derivatives incorporating a hippuric acid moiety: Synthesis and evaluation of antibacterial and antifungal activities, European Journal of Medicinal Chemistry (2013), 64, 111–120.
[4]	I. A. Cuadra, A. Cabañas, J. A. R. Cheda, M. Türk, C. Pando, Cocrystallization of the anticancer drug 5-fluorouracil and coformers urea, thiourea or pyrazinamide using supercritical CO₂ as an antisolvent (SAS) and as a solvent (CSS), Journal of Supercritical Fluids. (2020), 160, 104813.
[5]	R. A. K. Al-Harbi, M. A. M. S. El-Sharief, S. Y. Abbas, Synthesis and anticancer activity of bis-benzo[d][1,3]dioxol-5-yl thiourea derivatives with molecular docking study, Bioorganic Chemistry (2019), 90, 103088.
[6]	B. Phetsuksiri, J. Mary, H. Scherman, M. McNeil, G. S. Besra, A.R. Baulard, R. A. Slayden, A. E. DeBarber, C. E. Barry, B. Baird, D. C. Crick, P. J. Brennan, Unique Mechanism of Action of the Thiourea Drug Isoxyl on Mycobacterium tuberculosis, Journal of Biological Chemistry (2003), 53123–53130.
[7]	B. Ullah, Y. Zhou, J. Chen, Z. Bao, Y. Yang, Q. Yang, Q. Ren, Z. Zhang, New catalytic effect of thiourea on the oxidative cyanation of N-aryltetrahydroisoquinolines, Tetrahedron Letters (2019), 60, 348–351.
[8]	H. Alamgholiloo, S. Rostamnia, N. N. Pesyan, Anchoring and stabilization of colloidal PdNPs on exfoliated bis-thiourea modified graphene oxide layers with super catalytic activity in water and PEG, Colloids Surfaces A Physicochemical Engineering Aspects (2020), 602, 125130.
[9]	M. Breton, M. Bessodes, S. Bouaziz, J. Herscovici, D. Scherman, N. Mignet, Iminothiol/thiourea tautomeric equilibrium in thiourea lipids impacts DNA compaction by inducing a cationic nucleation for complex assembly, Biophysical Chemistry (2009), 145, 7–16.
[10]	M. S. M. Yusof, M. A. Ibarahim, N. M. Amin, V. Supramaniam, B. M. Yamin, Antibacterial evaluations of novel carbonyl thiourea derivatives., UKM-ITB. VIII (2009) 263–268.
[11]	N. I. M. Halim, K. Kassim, A. H. Fadzil, B. M. Yamin, Synthesis, Characterization and Antibacterial Studies of 1,2–Bis(N’-2,3 and 4-methoxybenzoylthioureido)-4-nitrobenzene, APCBEE Procedia (2012), 3, 129–133.
[12]	P. K. Paul, M. Yadav, Investigation on corrosion inhibition and adsorption mechanism of triazine-thiourea derivatives at mild steel / HCl solution interface: Electrochemical, XPS, DFT and Monte Carlo simulation approach, Journal of Electroanalytical Chemistry (2020), 877, 114599.
[13]	S. Fatima, R. Sharma, F. Asghar, A. Kamal, A. Badshah, H.-B. Kraatz, Study of new amphiphiles based on ferrocene containing thioureas as efficient corrosion inhibitors: Gravimetric, electrochemical, SEM and DFT studies, Journal of Industrial and Engineering Chemistry (2019), 76, 374–387.
[14]	I. Samb, N. Gaye, R. Sylla-Gueye, E. I. Thiam, M. Gaye, P. Retailleau, Crystal structure of ıt N, N'-[(ethane-1,2-di-yl)bis-(aza-nediylcarbonothioyl)]bis-(benzamide), Acta Crystallographica E (2019), 75, 642–645.
[15]	E. I. Thiam, M. Diop, M. Gaye, A. S. Sall, A. H. Barry, 1,2-Bis(N'-benzoylthioureido)benzene, Acta Crystallographyca E (2008), 64, o776.
[16]	G. M. Sheldrick, ıt SHELXT – Integrated space-group and crystal-structure determination. Acta Crystallographica A (2015), 71, 3–8.
[17]	G. M. Sheldrick, Crystal structure refinement with ıt SHELXL. Acta Crystallographica C (2015), 71, 3–8.
[18]	L. J. Farrugia, ıt WinGX and ıt ORTEP for Windows: an update. Journal of Applied Crystallography (2012), 45, 849-854.
[19]	A. K. Singh, O. P. Pandey, S. K. Sengupta, Synthesis, spectral and antimicrobial activity of Zn(II) complexes with Schiff bases derived from 2-hydrazino-5-[substituted phenyl]-1,3,4-thiadiazole and benzaldehyde/2-hydroxyacetophenone/indoline-2,3-dione, Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy (2013), 113, 393–399.
[20]	F. Odame, E. C. Hosten, R. Betz, K. Lobb, Z. R. Tshentu, Characterization of some amino acid derivatives of benzoyl isothiocyanate: Crystal structures and theoretical prediction of their reactivity, Journal of Molecular Structure (2015), 1099, 38–48.
[21]	A. Saeed, N. Abbas, Z. Ashraf, M. Bolte, Synthesis, Characterization and Antibacterial Activity of New 1,2- and 1,4-Bis(N’-Substituted Thioureido)benzene Derivatives, South African Journal of Chemistry (2013), 66, 273–278.
[22]	L. A. Saghatforoush, S. Hosseinpour, M. W. Bezpalko, W. S. Kassel, X-ray crystal structural and spectral studies of copper(II) and nickel(II) complexes of functionalized bis(thiosemicarbazone) ligands and investigation of their electrochemical behavior, Inorganica Chimica Acta (2019), 484, 527–534.
[23]	S. Madabhushi, K. K. R. Mallu, V. S. Vangipuram, S. Kurva, Y. Poornachandra, C. G. Kumar, Synthesis of novel benzimidazole functionalized chiral thioureas and evaluation of their antibacterial and anticancer activities, Bioorganic Medicinal Chemistry Letters (2014), 24, 4822–4825.
[24]	B. M. Yamin, U. M. Osman, 1,2-Bis(N'-benzoylthioureido)-4-chlorobenzene, Acta Crystallographica E (2011), 67, o1286.

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APA Style

Fatou Faye, Rokhaya Sylla-Gueye, Ibrahima Elhadji Thiam, James Orton, Simon Coles, et al. (2020). Synthesis, Characterization and Crystal Structure of 1-(2-benzamidophenyl)-3-benzoylthiourea Hemihydrate. Science Journal of Chemistry, 8(6), 131-135. https://doi.org/10.11648/j.sjc.20200806.11

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ACS Style

Fatou Faye; Rokhaya Sylla-Gueye; Ibrahima Elhadji Thiam; James Orton; Simon Coles, et al. Synthesis, Characterization and Crystal Structure of 1-(2-benzamidophenyl)-3-benzoylthiourea Hemihydrate. Sci. J. Chem. 2020, 8(6), 131-135. doi: 10.11648/j.sjc.20200806.11

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AMA Style

Fatou Faye, Rokhaya Sylla-Gueye, Ibrahima Elhadji Thiam, James Orton, Simon Coles, et al. Synthesis, Characterization and Crystal Structure of 1-(2-benzamidophenyl)-3-benzoylthiourea Hemihydrate. Sci J Chem. 2020;8(6):131-135. doi: 10.11648/j.sjc.20200806.11

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@article{10.11648/j.sjc.20200806.11,
  author = {Fatou Faye and Rokhaya Sylla-Gueye and Ibrahima Elhadji Thiam and James Orton and Simon Coles and Mohamed Gaye},
  title = {Synthesis, Characterization and Crystal Structure of 1-(2-benzamidophenyl)-3-benzoylthiourea Hemihydrate},
  journal = {Science Journal of Chemistry},
  volume = {8},
  number = {6},
  pages = {131-135},
  doi = {10.11648/j.sjc.20200806.11},
  url = {https://doi.org/10.11648/j.sjc.20200806.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20200806.11},
  abstract = {The dissymmetric compound C21H17N3O2S.0.5H2O obtained by a reaction of 1,2-diaminobenzene, potassium thiocyanate and benzoyl chloride in 1/1/2 ratio is characterized by elemental analyses, IR, and NMR spectroscopies. The structure is elucidated by X-ray diffraction technic. The compound crystallizes in the monoclinic system with a space group of I2. The asymmetric unit contains one hemihydrate organic molecule. The title thiourea derivative, features an almost planar, C2N2S (S1/N1/N2/C7/C8) moiety, with a maximum deviation from the least-squares plane of 0.0422 (3) Å. This moiety is flanked by a disubstituted and a monosubstituted phenyl rings. The dihedral angles between the thiourea and the monosubstituted phenyl ring and the thiourea and the central disubstituted phenyl ring are respectively 10.418 (7)° and 60.292 (2)°, indicating twist in the molecule. On the other arm, a phenyl ring supported by an amide function, which is linked to the central ring through the nitrogen atom, is present. The dihedral angle between this phenyl group and the central disubstituted phenyl is 76.862 (7)° showing that their mean planes are not coplanar. Intramolecular S(thiono)—H…O(water) hydrogen bonds which close in S (6) and S (7) rings consolidate the conformation. Intermolecular N(amido)—H…O(carbonyl) which form layers parallel to the ac plane stabilized the structure.},
 year = {2020}
}

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TY - JOUR
T1 - Synthesis, Characterization and Crystal Structure of 1-(2-benzamidophenyl)-3-benzoylthiourea Hemihydrate
AU - Fatou Faye
AU - Rokhaya Sylla-Gueye
AU - Ibrahima Elhadji Thiam
AU - James Orton
AU - Simon Coles
AU - Mohamed Gaye
Y1 - 2020/12/11
PY - 2020
N1 - https://doi.org/10.11648/j.sjc.20200806.11
DO - 10.11648/j.sjc.20200806.11
T2 - Science Journal of Chemistry
JF - Science Journal of Chemistry
JO - Science Journal of Chemistry
SP - 131
EP - 135
PB - Science Publishing Group
SN - 2330-099X
UR - https://doi.org/10.11648/j.sjc.20200806.11
AB - The dissymmetric compound C21H17N3O2S.0.5H2O obtained by a reaction of 1,2-diaminobenzene, potassium thiocyanate and benzoyl chloride in 1/1/2 ratio is characterized by elemental analyses, IR, and NMR spectroscopies. The structure is elucidated by X-ray diffraction technic. The compound crystallizes in the monoclinic system with a space group of I2. The asymmetric unit contains one hemihydrate organic molecule. The title thiourea derivative, features an almost planar, C2N2S (S1/N1/N2/C7/C8) moiety, with a maximum deviation from the least-squares plane of 0.0422 (3) Å. This moiety is flanked by a disubstituted and a monosubstituted phenyl rings. The dihedral angles between the thiourea and the monosubstituted phenyl ring and the thiourea and the central disubstituted phenyl ring are respectively 10.418 (7)° and 60.292 (2)°, indicating twist in the molecule. On the other arm, a phenyl ring supported by an amide function, which is linked to the central ring through the nitrogen atom, is present. The dihedral angle between this phenyl group and the central disubstituted phenyl is 76.862 (7)° showing that their mean planes are not coplanar. Intramolecular S(thiono)—H…O(water) hydrogen bonds which close in S (6) and S (7) rings consolidate the conformation. Intermolecular N(amido)—H…O(carbonyl) which form layers parallel to the ac plane stabilized the structure.
VL - 8
IS - 6
ER -

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Author Information

Fatou Faye

Department of Chemistry, University Cheikh Anta Diop, Dakar, Senegal
Rokhaya Sylla-Gueye

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

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

UK National Crystallography Service, School of Chemistry, Southampton, United Kingdom
Simon Coles

UK National Crystallography Service, School of Chemistry, Southampton, United Kingdom
Mohamed Gaye

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

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APA Style

Fatou Faye, Rokhaya Sylla-Gueye, Ibrahima Elhadji Thiam, James Orton, Simon Coles, et al. (2020). Synthesis, Characterization and Crystal Structure of 1-(2-benzamidophenyl)-3-benzoylthiourea Hemihydrate. Science Journal of Chemistry, 8(6), 131-135. https://doi.org/10.11648/j.sjc.20200806.11

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ACS Style

Fatou Faye; Rokhaya Sylla-Gueye; Ibrahima Elhadji Thiam; James Orton; Simon Coles, et al. Synthesis, Characterization and Crystal Structure of 1-(2-benzamidophenyl)-3-benzoylthiourea Hemihydrate. Sci. J. Chem. 2020, 8(6), 131-135. doi: 10.11648/j.sjc.20200806.11

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AMA Style

Fatou Faye, Rokhaya Sylla-Gueye, Ibrahima Elhadji Thiam, James Orton, Simon Coles, et al. Synthesis, Characterization and Crystal Structure of 1-(2-benzamidophenyl)-3-benzoylthiourea Hemihydrate. Sci J Chem. 2020;8(6):131-135. doi: 10.11648/j.sjc.20200806.11

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@article{10.11648/j.sjc.20200806.11,
  author = {Fatou Faye and Rokhaya Sylla-Gueye and Ibrahima Elhadji Thiam and James Orton and Simon Coles and Mohamed Gaye},
  title = {Synthesis, Characterization and Crystal Structure of 1-(2-benzamidophenyl)-3-benzoylthiourea Hemihydrate},
  journal = {Science Journal of Chemistry},
  volume = {8},
  number = {6},
  pages = {131-135},
  doi = {10.11648/j.sjc.20200806.11},
  url = {https://doi.org/10.11648/j.sjc.20200806.11},
  eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20200806.11},
  abstract = {The dissymmetric compound C21H17N3O2S.0.5H2O obtained by a reaction of 1,2-diaminobenzene, potassium thiocyanate and benzoyl chloride in 1/1/2 ratio is characterized by elemental analyses, IR, and NMR spectroscopies. The structure is elucidated by X-ray diffraction technic. The compound crystallizes in the monoclinic system with a space group of I2. The asymmetric unit contains one hemihydrate organic molecule. The title thiourea derivative, features an almost planar, C2N2S (S1/N1/N2/C7/C8) moiety, with a maximum deviation from the least-squares plane of 0.0422 (3) Å. This moiety is flanked by a disubstituted and a monosubstituted phenyl rings. The dihedral angles between the thiourea and the monosubstituted phenyl ring and the thiourea and the central disubstituted phenyl ring are respectively 10.418 (7)° and 60.292 (2)°, indicating twist in the molecule. On the other arm, a phenyl ring supported by an amide function, which is linked to the central ring through the nitrogen atom, is present. The dihedral angle between this phenyl group and the central disubstituted phenyl is 76.862 (7)° showing that their mean planes are not coplanar. Intramolecular S(thiono)—H…O(water) hydrogen bonds which close in S (6) and S (7) rings consolidate the conformation. Intermolecular N(amido)—H…O(carbonyl) which form layers parallel to the ac plane stabilized the structure.},
 year = {2020}
}

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