Synthesis, Characterization and Crystal Structures of 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide and 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide

doi:10.3390/cryst2031108

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Crystals 2012, 2(3), 1108-1115; doi:10.3390/cryst2031108

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Synthesis, Characterization and Crystal Structures of 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide and 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide

Jerry P. Jasinski^1,* , James A. Golen¹, Seranthimata Samshuddin², Badiadka Narayana² and Hemmige S. Yathirajan³

¹ Department of Chemistry, Keene State College, 229 Main Street, Keene, NH 03435-2001, USA ² Department of Studies in Chemistry, Mangalore University, Mangalagangotri-574 199, India ³ Department of Studies in Chemistry, University of Mysore, Manasagangotri, Mysore-570 006, India

* Author to whom correspondence should be addressed.

Received: 28 June 2012; in revised form: 19 July 2012 / Accepted: 24 July 2012 / Published: 15 August 2012

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Abstract: Two new pyrazoline derivatives, 3,5-bis(4-fluorophenyl)-4,5-dihydropyrazole-1-carboxamide (1) and 3,5-bis(4-fluorophenyl)-4,5-dihydropyrazole-1-carbothioamide (2), were synthesized by reacting 4,4'-difluoro chalcone with semicarbazide hydrochloride and thiosemicarbazide in ethanolic sodium hydroxide solution. Both the compounds were confirmed by single crystal X-ray diffraction data and supported by IR, NMR, and mass spectral data. In 1, crystal packing is stabilized by N–H…O hydrogen bonds and weak N–H...N, N–H…F and C–H…F intermolecular interactions. In 2, only weak N–H…F and N–H…S intermolecular interactions are observed. Crystal data: C₁₆H₁₃F₂N₃O, (1), M_r= 301.29, monoclinic, C2/c, a = 17.6219(6) Å, b = 10.8735(3) Å, c = 15.3216(5) Å, β = 102.864(3)°, V = 2862.11(16) Å³, Z = 8, T = 173 K, R(F) = 0.0511, wR(F²) = 0.1333; C₁₆H₁₃F₂N₃S, (2), M_r= 317.35, monoclinic, P2₁/c, a = 14.339(2) Å, b = 11.1478(17) Å, c = 9.541(2)(5) Å, β = 107.007(18)°, V = 1458.5(5) Å³, Z = 4, T = 173 K, R(F) = 0.0413, wR(F²) = 0.0959.

Keywords: pyrazoline derivatives; X-ray crystal structure; hydrogen bonds; weak intermolecular interactions

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MDPI and ACS Style

Jasinski, J.P.; Golen, J.A.; Samshuddin, S.; Narayana, B.; Yathirajan, H.S. Synthesis, Characterization and Crystal Structures of 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide and 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide. Crystals 2012, 2, 1108-1115.

AMA Style

Jasinski JP, Golen JA, Samshuddin S, Narayana B, Yathirajan HS. Synthesis, Characterization and Crystal Structures of 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide and 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide. Crystals. 2012; 2(3):1108-1115.

Chicago/Turabian Style

Jasinski, Jerry P.; Golen, James A.; Samshuddin, Seranthimata; Narayana, Badiadka; Yathirajan, Hemmige S. 2012. "Synthesis, Characterization and Crystal Structures of 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carboxamide and 3,5-Bis(4-fluorophenyl)-4,5-dihydro-1H-pyrazole-1-carbothioamide." Crystals 2, no. 3: 1108-1115.

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