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Efficient Syntheses, Crystal Structure and Thermal Properties of Gabapentin 4-Acetamido, 2-Mesitylene and 2,4-Dinitro Sulfonamides Derivatives

  • Nosheen Kanwal
  • Islam Ullah KhanEmail author
  • Shahzad SharifEmail author
  • Erum Akbar Hussain
  • Arshad Mehmood
  • Onur Sahin
Original Paper

Abstract

Efficient syntheses of four derivatives G2–G5 of Gabapentin (G1) have been achieved. The structures of targeted compounds were investigated by elemental analysis, FT-IR, and 1H-NMR spectroscopic method. Crystal structures of G2 and G4 determined by single crystal X-ray diffraction method are also described. In G2 the molecules are stacked over each other in the form of layers and adjacent layers run parallel to each other. Intermolecular hydrogen bonding and van der Waals interactions are responsible for building the molecular assembly and packing of molecules in the unit. In G4, the molecules are arranged in parallel sheets formed by inter-molecular hydrogen bonds. The proposed synthetic route has high impact due to its simple reaction conditions of room temperature, water as a green solvent and short time to accomplish the reaction.

Graphical Abstract

Synthesis of Gabapentin sulfonamide derivatives and characterization by elemental analyzer, FT-IR, 1H-NMR, thermogravimetry and single crystal X-ray diffraction are described. The molecular structure of G4 showing the atom numbering scheme.

Keywords

Gabapentin Sulfonamides Synthesis Crystal structure Thermal analysis 

Notes

Acknowledgements

Authors would like to thank Prof. Dr. Nawaz Tahir for kind assistance in refinement of structure, Prof. Khalid M. Khan, HEJ Institute of Chemistry, University of Karachi and Dr. Saif Ullah Salik, University of Oxford, UK for 1H NMR and mass spectral analysis, Ms. Sidra Farid, Department of Chemistry, GCU, Lahore for her assistance in X-ray diffraction studies.

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Nosheen Kanwal
    • 1
  • Islam Ullah Khan
    • 2
    Email author
  • Shahzad Sharif
    • 2
    Email author
  • Erum Akbar Hussain
    • 1
  • Arshad Mehmood
    • 2
  • Onur Sahin
    • 3
  1. 1.Department of ChemistryLahore College for Women UniversityLahorePakistan
  2. 2.Department of ChemistryGovernment College UniversityLahorePakistan
  3. 3.Scientific and Technological Research Application and Research CenterSinop UniversitySinopTurkey

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