Experimental and theoretical studies on 4-(2,4-dichlorobenzylideneamino)antipyrine and 4-(2,6-dichlorobenzylideneamino)antipyrine

Sun, Yuxi; Wei, Wen-Xian; Hao, Qingli; Lu, Lude; Wang, Xin

doi:10.1016/j.saa.2009.03.028

Cited by 31 publications

(7 citation statements)

References 41 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…From Table 5, it can be appreciated that the highest total energies of -87.8 kJ/mol (1) and -86.7 kJ/mol (2) correspond to the molecular pair formed by N-H•••O bonds generating 𝑅 2 2 (10) ring motifs (see Figures 1b and 2b) being the shorter contact and the strongest interaction of all the hydrogen bonds that are responsible of the crystal packing of 1 and 2.…”

Section: Energy Frameworkmentioning

confidence: 99%

“…Interest in antipyrine derivatives (APDs) can be traced back to the synthesis of the first of such derivatives, namely aminophenazone, by Knorr in 1833 and have been the subject matter of research in a variety of fields [1]. Aminophenazone derivatives have been shown to possess pharmacological applications as antipyretic [2], analgesic [3], and anti-inflammatory agents [4,5].…”

Section: Introductionmentioning

confidence: 99%

“…We report here the synthesis and X-ray crystal structure of two new antipyrine derivatives, namely 2-bromo-N- (2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4-yl)benzamide (1) and 2-chloro-N- (2,3-dihydro-1,5-dimethyl-3-oxo-2-phenyl-1H-pyrazol-4yl)benzamide (2). Hirshfeld surface analysis was used to determine quantitatively the intermolecular interactions controlling the crystal packing of both compounds.…”

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

Intermolecular interactions in antipyrine-like derivatives 2-halo-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations

et al. 2020

View full text Add to dashboard Cite

show abstract

Section: Energy Frameworkmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Intermolecular interactions in antipyrine-like derivatives 2-halo-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Natural population analysis indicates that the electronic transitions are mainly derived from the contributions of bands p ? p* as reported literature [27]. As shown from The compound was synthesized as in Scheme 1 by the following procedure.…”

Section: Absorption Spectramentioning

confidence: 99%

Synthesis, Crystal Structure, Spectroscopic and Electronic Properties of (E)-Trans-2-(2-(Biphenyl-4-ylmethylene)Hydrazinyl)-4-(3-Methyl-3-Phenylcyclobutyl)Thiazole

et al. 2010

View full text Add to dashboard Cite

A new compound of (C 27 H 25 N 3 S) has been synthesized and characterized by 1 H NMR, 13 C NMR, IR, UV-Visible spectroscopy, and single crystal X-ray diffraction. The compound crystallizes in the monoclinic space group P2 1 /c and crystals of (I) were found approximately 0.5:0.5 ratio to be twinned. The crystal structure is stabilized by N-HÁÁÁN inter molecular hydrogen bonding. In addition to the molecular geometry and dimeric structure from X-ray experiment, the optimized molecular geometry for monomer and dimer, vibrational frequencies, atomic charges distribution, and total energies of the title compound in the ground state have been calculated using ab initio method. Density Functional Theory (B3LYP) and Hartree-Fock (HF) methods with basis sets 6-31G(d, p) and 3-21G were used in the calculations. Calculated frequencies are in good agreement with the corresponding experimental data. UV-Vis absorption spectra of the compound have been ascribed to their corresponding molecular structure and electrons orbital transitions.

show abstract

“…The above said parameters fit excellently to imine materials. Hence, the imino heterojunction organic materials are used as bio-functional compounds with excellent NLO responses [13][14][15][16][17][18][19]. We also know that the heterojunction units are the core structures of a number of natural products like imine acids, bioelectric and photovoltaic materials.…”

Section: Introductionmentioning

confidence: 99%

Studies on the Synthesis, Growth and Characterization of ([Paranitrophenyl]Imino)Benzene NLO Crystal by Sankaranarayanan-Ramasamy Method

Anbarasu¹,

Kumar²,

Devarajan³

2013

JMMCE

View full text Add to dashboard Cite

The study of imine-bridged organics has been the hot spot synthesis of second order nonlinear optical (SONLO) and photo-responsive materials in recent years. Herein we present a study of synthesis, growth, and characterization of ([paranitrophenyl]imino)benzene (PNPIB) NLO single crystal. The title compound was synthesized in one step by Schiff base formation. <110> PNPIB single crystal of diameter of 40 mm and length 50 mm was successfully grown by SR method using a seed as the nucleus. The growth rate formula is derived for the SR method. PNPIB single crystals of 10 mm diameter and 60 mm height have been grown at an average growth rate of 3 mm per day from the point seed in a glass crystallizer. Almost 100% stable crystal conversion efficiency was achieved. The as grown PNPIB crystals were characterized using single crystal X-ray diffraction (XRD), X-ray powder diffraction (XRPD), Fourier Transform Infrared (FTIR), Ultraviolet-Visible-Near Infrared (UV-Vis-NIR), 1 H & 13C NMR spectral studies, dielectric measurement and NLO studies. Single crystal XRD analysis confirms that the grown ingot belongs to the space group of P 2 of monoclinic system thus exhibiting noncentrosymmetric structure. The crystalline perfection was assessed by XRPD. The powder diffraction pattern of the grown crystal has been indexed. The presence of C=N bond with intramolecular hydrogen bonding and the protonation of ions were confirmed by FTIR analysis. The UV-Vis-NIR spectrum of the crystal shows that the crystal has a cut-off at 298 nm. The 1 H & 13 C NMR spectra confirm the molecular structure. The dielectric behaviour was measured in the frequency range 1 KHz -10 KHz for the temperature range from 30˚C to 170˚C. The slight decrease in dielectric constant has been observed as the frequency is increased and the dielectric loss is very low for the entire frequency range. The second harmonic generation (SHG) in the crystal was observed by Kurtz powder technique.

show abstract

Experimental and theoretical studies on 4-(2,4-dichlorobenzylideneamino)antipyrine and 4-(2,6-dichlorobenzylideneamino)antipyrine

Cited by 31 publications

References 41 publications

Intermolecular interactions in antipyrine-like derivatives 2-halo-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations

Intermolecular interactions in antipyrine-like derivatives 2-halo-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl)benzamides: X-ray structure, Hirshfeld surface analysis and DFT calculations

Synthesis, Crystal Structure, Spectroscopic and Electronic Properties of (E)-Trans-2-(2-(Biphenyl-4-ylmethylene)Hydrazinyl)-4-(3-Methyl-3-Phenylcyclobutyl)Thiazole

Studies on the Synthesis, Growth and Characterization of ([Paranitrophenyl]Imino)Benzene NLO Crystal by Sankaranarayanan-Ramasamy Method

Contact Info

Product

Resources

About