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

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), 2020. Published by Science Publishing Group

Keywords

1,2-diaminobenzene, Benzoyl Chloride, Potassium Thiocyanate

References
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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
  • 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

  • UK National Crystallography Service, School of Chemistry, Southampton, United Kingdom

  • UK National Crystallography Service, School of Chemistry, Southampton, United Kingdom

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

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