Crystal structure of (Z)-2-[(E)-2-benzylidenehydrazin-1-ylidene]-1,2-diphenylethanone

Abstract

The title compound has an almost planar 1,2-di­benzyl­idenehydrazine backbone with an approximately orthogonal planar phenyl ethanone substituent on one of the imine C atoms. In the crystal, mol­ecules are linked via C—H⋯O hydrogen bonds and C—H⋯π inter­actions, forming a three-dimensional structure.

Crystal structure and molecular docking study of (E)-2-{[(E)-2-hydroxy-5-methylbenzylidene]hydrazinylidene}-1,2-diphenylethan-1-one

“…These results suggest single-bond character for C17-O2 and C15-C16 and double-bond character for the C15-N2 bond as expected for a phenol-imine structure (Kaştaş et al, 2020). The bond lengths and angles in the title molecule agree reasonably well with those found in closely related structures (Bouchama et al, 2015;Wieland et al, 2011). Based on the refinement parameters, the tautomeric form of the compound is the phenol-imine form in which the tautomeric proton (H2) is located on the phenolic oxygen atom (O2).…”

“…The C7-C8 bond distance of 1.523 (2) Å corresponding to the value expected for a Csp 2 -Csp 2 single bond, is slightly longer than observed for the title compound [1.472 ( 5) Å ]. This bond length is shorter than in NOTZIH [1.528 (3) Å ; Bouchama et al, 2015]. In HULFAX (Elmacı et al, 2015), the C15-N2 bond length [1.276 ( 4) Å ] is typical of for an azomethine C N bond and shorter than in the title compound [1.287 ( 5) Å ].…”

Synthesis, molecular structure analyses and DFT studies on new asymmetrical azines based Schiff bases

“…153°C). [30] A mixture of benzaldehyde (1.06 g, 0.01 mol), benzil (2.10 g; 0.01 mol) and hydrazine hydrate (0.32 g, 0.01 mol) in 50 ml of ethanol containing 2 drops of acetic acid was refluxed for about 2 h. The reaction was monitored by TLC until completion. Excess solvent was evaporated under vacuum and the resulting yellow solid product was recrystallized from absolute ethanol to afford yellow needles of the title compound (yield 75%; m.p.…”

“…In recent years, computational studies on azines have been conducted to study their molecular properties, which involves the theoretical and experimental characterization of their electronic structure [23][24][25][26], including their conformational equilibrium structure, their tautomerism, their NMR spectra and potential energy distribution (PED) vibration frequencies [27][28]. The importance given to azine derivatives due to their wide application in various scientific fields was considered a research project in our laboratory [29][30]. Different methods of synthesis of symmetrical and unsymmetrical azines are reported [3,13,31] where the first cited are easily obtained, while their asymmetrical counterparts, they are it under harsher conditions [31,[32][33].…”

“…We then borrowed this new method which proves efficient and practical, on which we made a minor modification of the reaction conditions as indicated in the experimental part. We report in this paper the synthesis of two new unsymmetrical azines (compounds (I) and (II)) isolated with relatively good yields whose structures were characterized using FT-IR, UV-Vis and single-crystal X-ray diffraction techniques performed on single crystals on the one hand and a Density Functional Theory (DFT) calculations and Time-Dependent DFT (TDDFT) calculations are performed to get better insight into the geometrical and electronic properties, and to give a detailed description of structures spectroscopic assignments of the IR and UV-visible for the three unsymmetrical azines compound : I, II, III on the other hand, whose crystalline structure of the latter is reported [30]. The general structures of these compounds are given in scheme 1.…”