Molecular and crystal engineering of a semicarbazide–ketone condensate: A multitechnique characterization

  • Fatou Dieng Laboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Sénégal
  • Papa Aly Gueye Laboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Sénégal
  • Mouhamadou Birame Diop Laboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Sénégal
  • Adrienne Ndiolene Laboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Sénégal
  • Mouhamadou Sembene Boye Département de Physique Chimie, Faculté des Sciences et Technologies de l’éducation et de la formation, Boulevard Habib Bourguiba, Université Cheikh Anta Diop, 5036 Fann-Dakar, Sénégal
  • Shova Sergiu Inorganic Polymers Department, “Petru Poni” Institute of Macromolecular Chemistry, Alea Gr. Ghica Voda 41A, Iasi 700487, Romania
  • Aminata Diassé-Sarr Laboratoire de Chimie Minérale et Analytique, Département de Chimie, Faculté des Sciences et Techniques, Université Cheikh Anta Diop, Dakar, Sénégal
DOI: https://doi.org/10.34198/ejcs.12425.379396
Keywords: single crystal X-ray, semicarbazide condensation, spectroscopic characterization, Hirshfeld surface analysis, supramolecular assembly

Abstract

The studied organic compound, namely (2Z)-2-(2-chloro-1-phenylethylidene)hydrazine-1-carboxamide was synthesized via a condensation reaction between semicarbazide hydrochloride and α-chloroacetophenone, affording a hydrazone–carboxamide derivative in good yield. Its structure was elucidated using single crystal X-ray crystallography, ATR-FTIR, 1H NMR, 13CNMR, DEPT 135°, and Hirshfeld surface analysis. The compound [C6H5-C(CH2Cl)N=NH-C(O)NH2] (1), crystallizes in the monoclinic space group P21/C with Z = 4, a = 10.6213(8) Å, b = 7.2518(5) Å, c = 13.6791(9) Å, β = 101.018(7)° and V = 1034.19(13) Å3. ATR-FTIR and NMR data confirmed the presence of a monosubstituted aromatic ring, a chloromethyl side chain, and a conjugated hydrazone–amide moiety. Single-crystal X-ray analysis revealed typical metrics consistent with a C=N double bond and a urea-like C=O(–NH2) fragment. In the crystal, molecules are linked by directional N–H···O and N–H···N hydrogen bonding patterns, giving rise to centrosymmetric  dimers, extended  rings, and larger  macrocyclic assemblies, generating a two-dimensional supramolecular network parallel to the (100) plane. Hirshfeld surface analysis supported the dominance of hydrogen bonding in the packing arrangement and confirmed the absence of significant π···π stacking interactions. These results achieve the critical role of hydrogen bonding in directing the crystal architecture and stabilizing the structure.

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Published
2025-09-11
How to Cite
Dieng, F., Gueye, P. A., Diop, M. B., Ndiolene, A., Boye, M. S., Sergiu, S., & Diassé-Sarr, A. (2025). Molecular and crystal engineering of a semicarbazide–ketone condensate: A multitechnique characterization . Earthline Journal of Chemical Sciences, 12(4), 379-396. https://doi.org/10.34198/ejcs.12425.379396
Issue
Vol 12 No 4 (2025): In progress
Section
Articles


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