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.
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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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Kanwal, N., Khan, I.U., Sharif, S. et al. Efficient Syntheses, Crystal Structure and Thermal Properties of Gabapentin 4-Acetamido, 2-Mesitylene and 2,4-Dinitro Sulfonamides Derivatives. J Chem Crystallogr 49, 162–168 (2019). https://doi.org/10.1007/s10870-018-00765-2
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DOI: https://doi.org/10.1007/s10870-018-00765-2