Synthesis, Crystal Structure, Hirshfeld Surface Analysis, DFT, and DNA-Binding Studies of (E)-2-(3-Hydroxy-4-Methoxybenzylidene)Hydrazinecarbothioamide

  • Pervaiz Ali Channar
  • Nasima ArshadEmail author
  • Shahid Iqbal Farooqi
  • Fayaz Ali Larik
  • Aamer SaeedEmail author
  • Tuncer Hökelek
  • Syeda Aaliya Shehzadi
  • Nasir Abbas
  • Ulrich Flörke


(E)-2-(3-Hydroxy-4-methoxybenzylidene)hydrazinecarbothioamide 3 was synthesized by reacting thiosemicarbazide with 2-hydorxy-3-methoxybenzaldehyde in dry ethanol. The structure was elucidated by spectroscopic (FT-IR, 1H NMR, and 13C NMR) and single crystal X-ray diffraction techniques. A detailed analysis of the intermolecular interactions has been performed based on the Hirshfeld surfaces and their associated two-dimensional fingerprint plots. DFT, spectroscopic, and electrochemical DNA-binding analysis confirmed that the compound is reactive to bind with DNA. Viscometric studies suggested that compound 3 has a mixed mode of interaction and intercalated into the DNA base pairs predominantly along with the possibility of electrostatic interactions.

Graphical Abstract


Azomethine X-ray analysis Hirshfeld surface analysis DFT analysis DNA-binding studies 



The authors would like to thank all the mentioned departments of national and international universities/institutes for the accomplishment of research explored in this paper.

Compliance with Ethical Standards

Conflicts of Interest

The authors declare that they have no conflict of interest.

Supplementary material

12010_2019_3008_MOESM1_ESM.txt (392 kb)
ESM 1 (TXT 391 kb)
12010_2019_3008_MOESM2_ESM.docx (31 kb)
ESM 2 (DOCX 31 kb)


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

Authors and Affiliations

  1. 1.Department of ChemistryQuaid-i-Azam UniversityIslamabadPakistan
  2. 2.Department of Chemistry, Faculty of SciencesAllama Iqbal Open UniversityIslamabadPakistan
  3. 3.Department of Physics, Faculty of EngineeringHacettepe UniversityBeytepeTurkey
  4. 4.Sulaiman Bin Abdullah Aba Al-Khail-Centre for Interdisciplinary Research in Basic Sciences (SA-CIRBS)International Islamic University, IslamabadIslamabadPakistan
  5. 5.Department Chemie, Fakultätfür NaturwissenschaftenUniversität PaderbornPaderbornGermany

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