Journal of Chemical Crystallography

, Volume 44, Issue 1, pp 51–56 | Cite as

Syntheses, Crystal Structures and Antimicrobial Studies of Two New Semicarbazone Derivatives

  • Tze Shyang Chia
  • Ching Kheng Quah
  • Chin Wei Ooi
  • B. Garudachari
  • Nishitha A. Isloor
  • Arun M. Isloor
  • Hoong-Kun Fun
Original Paper
First Online:
Received:
Accepted:

Abstract

Two new derivatives of semicarbazone, (E)-2-(hexan-2-ylidene)hydrazinecarboxamide and (E)-2-(heptan-2-ylidene)hydrazinecarboxamide were synthesized and characterized by IR and 1H NMR. Their crystal structures were characterized by X-ray diffraction method. Compound (I) crystallizes in triclinic \(P\overline{1}\), a = 6.7679(7) Å, b = 7.1912(8) Å, c = 9.9969(11) Å, α = 108.824(2)°, β = 99.398(3)°, γ = 92.680(2)°, V = 451.75(8) Å3, Z = 2, R 1 = 0.043 and wR 2 = 0.140. Compound (II) crystallizes in triclinic \(P\overline{1}\), a = 6.7192(6) Å, b = 7.2094(6) Å, c = 11.2842(11) Å, α = 103.303(2)°, β = 106.198(2)°, γ = 91.219(1)°, V = 508.70(8) Å3, Z = 2, R 1 = 0.044 and wR 2 = 0.133. Their molecules adopt a L-shape conformation with C atom in C=N double bond acting as the junction point. The C=O double bond indicate the existence of semicarbazone group in keto-like form for both compounds in their solid state. In the crystal, the carbonyl O atom for both derivatives acts as a common acceptor in the intermolecular bifurcated N–H···O hydrogen bonding which linked the molecules into one-dimensional supramolecular ribbons. Antimicrobial studies by serial dilution method showed both compounds exhibit antibacterial property.

Graphical Abstract

Two new semicarbazone derivatives are characterized by IR, 1H NMR and single crystal X-ray diffraction methods and their antibacterial activity was further investigated by screening against four different bacterial strains.

Keywords

Semicarbazone X-ray diffraction Crystal structure Hydrogen bond 
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Notes

Acknowledgments

The authors thank Universiti Sains Malaysia (USM) for the Research University Grant (1001/PFIZIK/811160), APEX DE2012 Grant (1002/PFIZIK/910323) and Research University Cluster Grant (1001/PSKBP/8630013). TSC thanks the Malaysian government and USM for the award of Research Fellowship. AMI thanks Prof. Swapan Bhattacharya, Director, NITK Surathkal, India for the encouragements. The authors extend their appreciation to The Deanship of Scientific Research at King Saud University for the funding the work through the research group Project No. RGP-VPP-207.

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • Tze Shyang Chia
    • 1
  • Ching Kheng Quah
    • 1
  • Chin Wei Ooi
    • 1
  • B. Garudachari
    • 3
  • Nishitha A. Isloor
    • 4
  • Arun M. Isloor
    • 3
  • Hoong-Kun Fun
    • 1
    • 2
  1. 1.X- ray Crystallography Unit, School of PhysicsUniversiti Sains MalaysiaMindenMalaysia
  2. 2.Department of Pharmaceutical Chemistry, College of PharmacyKing Saud UniversityRiyadhSaudi Arabia
  3. 3.Medicinal Chemistry Laboratory, Department of ChemistryNational Institute of Technology KarnatakaSurathkal, MangaloreIndia
  4. 4.Biotechnology Division, Department of Chemical EngineeringNational Institute of Technology KarnatakaSurathkal, MangaloreIndia

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