Synthesis, crystal structure, and antidiabetic property of hydrazine functionalized Schiff base: 1,2-Di(benzylidene)hydrazine

Nilankar Diyali; Meena Chettri; Abhranil De; Bhaskar Biswas

doi:10.5155/eurjchem.13.2.234-240.2265

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Published: Jun 30, 2022

DOI: https://doi.org/10.5155/eurjchem.13.2.234-240.2265

Keywords:

Synthesis, Hydrazine, Schiff base, Antidiabetic activity, X-ray crystal structure, Structural characterization

Section

Research Article

Issue

Vol. 13 No. 2 (2022): June 2022

Dates

Received 2022-03-10
Accepted 2022-04-09
Published 2022-06-30

Nilankar Diyali

Department of Chemistry, University of North Bengal, Darjeeling, 734013, India

https://orcid.org/0000-0002-1064-8308

Meena Chettri

Department of Chemistry, University of North Bengal, Darjeeling, 734013, India

https://orcid.org/0000-0003-2821-8880

Abhranil De

Department of Chemistry, University of North Bengal, Darjeeling, 734013, India

https://orcid.org/0000-0002-6131-2548

Bhaskar Biswas

Department of Chemistry, University of North Bengal, Darjeeling, 734013, India

https://orcid.org/0000-0002-5447-9729

Abstract

Hydrazine functionalized Schiff base, 1,2-di(benzylidene)hydrazine has been synthesized through a condensation between hydrazine and benzaldehyde under reflux, and structurally characterized. The crystal structure analysis reveals that the Schiff base crystallizes in an orthorhombic crystal system with the Pbcn space group. Crystal data for C₁₄H₁₂N₂: a = 13.130(2) Å, b = 11.801(2) Å, c = 7.5649(16) Å, V = 1172.1(4) Å³, Z = 4, T = 298.0(2) K, μ(MoKα) = 0.071 mm^-1, Dcalc = 1.180 g/cm³, 10252 reflections measured (6.206° ≤ 2Θ ≤ 65.352°), 2027 unique (R_int = 0.0381, R_sigma = 0.0283) which were used in all calculations. The final R₁ was 0.0627 (I > 2σ(I)) and wR₂ was 0.2462 (all data). It is evident that the imine protons are intramolecularly locked with the imine-N bond, and the phenyl rings exist in anti orientation with respect to the =N-N= bond adopting a nearly planar conformation. The Schiff base grows a one-dimensional framework in the crystalline phase through long-distant C-H···π interaction. Hirshfeld surface and energy framework analyses have also been performed to understand the supramolecular forces and their contributions meticulously. The hydrazine functionalized Schiff base showed an excellent antidiabetic activity through α-amylase inhibitory assay relative to a standard compound, acarbose under an identical condition.

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Diyali, N.; Chettri, M.; De, A.; Biswas, B. Synthesis, Crystal Structure, and Antidiabetic Property of Hydrazine Functionalized Schiff Base: 1,2-Di(benzylidene)hydrazine. Eur. J. Chem. 2022, 13, 234-240.

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