Synthesis, characterization, crystal structure and DFT studies on 1-acetyl-3-(2,4-dichloro-5-fluoro-phenyl)-5-phenyl-pyrazoline

Jian, Fang‐Fang; Zhao, Pusu; Guo, Huan-Mei; Li, Yufeng

doi:10.1016/j.saa.2007.05.016

Cited by 24 publications

(13 citation statements)

References 22 publications

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“…In the pyrazolinyl ring, the C8-N2 and C10=N1 bond lengths, 1.483 (2) and 1.2860 (18) Å, respectively, are comparable with those in similar structures [C-N 1.482 (2)-1.515 (9) A°, C=N 1.291 (2)-1.300 (10) A°]. The N1-N2 bond length of 1.3867 (16) Å is slightly longer than that found in a similar structure [N-N 1.373 (2)-1.380 (8) A°] (Jian et al, 2008). The plane containing the pyrazoline moiety is inclined to the adjacent phenyl ring (C16-C21) by 6.49 (9)\%, while the 4-methoxy substituted phenyl ring (C2-C7) is inclined to the pyrazoline moiety by 82.99 (9) °.…”

Section: D-hásupporting

confidence: 83%

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1-[5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone

et al. 2010

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The title molecule, C18H18N2O2, is V-shaped with the pyrazoline moiety being inclined to the adjacent phenyl ring by an angle of 6.49 (9)°, while the 4-methoxy-substituted ring is inclined to the pyrazoline ring by 82.99 (9)°. In the crystal, adjacent molecules are linked by C—H⋯O interactions, forming chains propagating in [100]. There are also C—H⋯π interactions involving adjacent molecules and those related by an inversion center.

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Section: D-hásupporting

confidence: 83%

“…For the synthesis and crystal structure of alkoxy group-bearing 2-pyrazoline derivatives, see: Abbas et al (2010); Bai et al (2009) ;Lu et al (2008); Fahrni et al (2003); Jian et al (2008 Table 1 Hydrogen-bond geometry (Å , ).…”

Section: Related Literaturementioning

confidence: 99%

1-[5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone

et al. 2010

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“…23 A number of papers have recently appeared in the literature concerning the calculation of vibrational assignments by quantum-chemistry methods. [24][25][26][27][28] These papers indicate that geometry optimization is a crucial factor in an accurate determination of computed vibrational frequencies. Moreover, it is known that the density functional theory (DFT) adequately takes into account electron correlation contributions, which are especially important in systems containing extensive electron conjugation and/or electron lone pairs.…”

Section: Introductionmentioning

confidence: 99%

Experimental and ab initio Computational Studies on Dimethyl-(4-{4-{3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-hydrazonomethyl}-phenyl)-amine

Yüksektepe¹,

Saraçoğlu²,

Çalışkan³

et al. 2010

Bulletin of the Korean Chemical Society

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A new hydrazone derivative compound has been synthesized and characterized by IR, 1 H-NMR, 13 C-NMR and UV-vis. spectroscopy techniques, elemental analysis and single-crystal X-ray diffraction (XRD). The new compound crystallizes in monoclinic space group C2/c. In addition to the crystal structure from X-ray experiment, the molecular geometry, vibrational frequencies and frontier molecular orbitals analysis of the title compound in the ground state have been calculated by using the HF/6-31G(d, p), B3LYP/6-311G(d, p) and B3LYP/6-31G(d, p) methods. The computed vibrational frequencies are used to determine the types of molecular motions associated with each of the observed experimental bands. To determine conformational flexibility, molecular energy profile of (1) was obtained by semi-empirical (AM1) calculation with respect to a selected degree of torsional freedom, which was varied from -180 o to +180 o in steps of 10 o . Molecular electrostatic potential of the compound was also performed by the theoretical method.

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“…These values indicate that the rings are planar in both compounds. This situation together with the shorter C9-C3 bond distances, 1.431(3) and 1.456(6) Å , respectively, which indicates double bond character [48,49], proves the conjugation between pyrazoline and heterocyclic rings. The conjugation causes also to lengthen the N2-C3 bonds in 3 and 4, with 1.291(2) and 1.287(5) Å , respectively.…”

Section: Resultsmentioning

confidence: 84%

Synthesis, Crystal Structure and Thermal Properties of N-Acetyl-3-(2-furyl)-5-ferrocenyl-2-pyrazoline and N-Acetyl-3-(2-thienyl)-5-ferrocenyl-2-pyrazoline

et al. 2012

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Two novel ferrocenyl substituted N-acetyl-2-pyrazolines, N-acetyl-3-(2-furyl)-5-ferrocenyl-2-pyrazoline (3) and N-acetyl-3-(2-thienyl)-5-ferrocenyl-2-pyrazoline (4), have been synthesized and characterized by FTIR, 1 H-NMR, 13 C-NMR techniques, elemental analysis and X-ray structure analysis. Thermal properties of these compounds have been determined by TGA, DTA and DSC analysis. Compound 3 (C 19 H 18 N 2 O 2 Fe) crystallizes in the monoclinic space group P21/c and Z = 4, with a = 8.6970(4) Å , b = 18.4725(9) Å , c = 11.0041(5) Å , b = 110.942(3)°.Compound 4 (C 19 H 18 N 2 OSFe) crystallizes in the orthorhombic space group Fdd2 and Z = 16, with a = 84.242(2) Å , b = 13.5416(5) Å , c = 5.9405(2) Å , b = 90°. In terms of crystal packing, each compound shows different molecular arrangement, which are stabilized by C-HÁÁÁO intermolecular weak hydrogen bonds, and/or C-HÁÁÁp interactions.

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Synthesis, characterization, crystal structure and DFT studies on 1-acetyl-3-(2,4-dichloro-5-fluoro-phenyl)-5-phenyl-pyrazoline

Cited by 24 publications

References 22 publications

1-[5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone

1-[5-(4-Methoxyphenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl]ethanone

Experimental and ab initio Computational Studies on Dimethyl-(4-{4-{3-methyl-3-phenyl-cyclobutyl)-thiazol-2-yl]-hydrazonomethyl}-phenyl)-amine

Synthesis, Crystal Structure and Thermal Properties of N-Acetyl-3-(2-furyl)-5-ferrocenyl-2-pyrazoline and N-Acetyl-3-(2-thienyl)-5-ferrocenyl-2-pyrazoline

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