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

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 (Rint = 0.0381, Rsigma = 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.

A new hydrazide functionalized Schiff’s base derivative: Insights into crystallography, Hirshfeld surface, and energy framework analysis

“…This target is achieved through self-assembly of molecular subunits, called supramolecular synthons, through noncovalent interactions. Desiraju et al coined the building blocks of supramolecular synthesis as supramolecular synthons, an entity that is very similar to covalent synthons in retrosynthesis, as put forward by Corey et al [6][7][8]. Reddy and coworkers advanced this idea to a greater extent by adding the context of supramolecular shape synthons, which focus on shape complementarity along with isotropic/anisotropic weak contacts for the rational design of mechanically flexible molecular single crystals [5].…”

“…Noncovalent interactions like hydrogen bonding, π•••π interaction, σ-hole interactions like chalcogen bonding, halogen bonding, spodium bonding, etc. play a decisive role in the molecular packing inside the crystal lattice to develop the crystal framework [4][5][6][7][8][9][10][11][12][13]. For a feasible weak interaction to happen, the strength of an interaction should be above kT in energy (k = Boltzmann constant) whose value is 0.6 kcal/mol at room temperature.…”

“…Another significant aspect for supramolecular crystal architecture formation is directionality of involved weak interactions. Desiraju et al pointed out that the most important directional interaction in molecular crystals is hydrogen bonding whose anisotropic property helps in designing molecular crystals with pre-desired packing and properties [1,[6][7][8][9][10][11][12][13][14][15][16]. Therefore, the holistic approach to the study of such weak interactions is very essential to understand the structure-mechanical property relationship of organic molecular crystals [15,16].…”