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Title: Synthesis, characterization, crystal structure, and thermal analysis of 2-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) acetamide

Abstract

The title compound, C{sub 13}H{sub 14}O{sub 2}N{sub 3}Cl, has been synthesized by the reaction of chloroacetyl chloride with 4-aminoantipyrine in basic media and characterized by FT-IR, CHN elemental analysis, UV-Vis, TGA, DTA, DSC and single crystal X-ray diffraction. crystals are monoclinic, sp. gr. P2{sub 1}/c, a = 6.9994(6), b = 12.4035(13), c = 15.836(2) Å, β = 100.367(9)°, Z = 4. The crystal structure is stabilized by N–H···O and C–H···O interactions, the former interactions result in the formation of dimers corresponding to R{sub 2}{sup 2} (10) graphset motif and the dimers are further connected by C–H···O hydrogen bonding forming chains. In addition, the thermal stability of the compound was determined by TGA, DTA, DSC analysis, and absorption at λ{sub max} = 298 nm was determined by UV-Vis spectrophotometer.

Authors:
 [1]; ;  [2];  [1]
  1. University of Jammu, X-ray Crystallography Laboratory, Post-Graduate Department of Physics & Electronics (India)
  2. Mangalore University, Mangalagangotri, Department of Studies in Chemistry (India)
Publication Date:
OSTI Identifier:
22472044
Resource Type:
Journal Article
Resource Relation:
Journal Name: Crystallography Reports; Journal Volume: 60; Journal Issue: 7; Other Information: Copyright (c) 2015 Pleiades Publishing, Inc.; Country of input: International Atomic Energy Agency (IAEA)
Country of Publication:
United States
Language:
English
Subject:
75 CONDENSED MATTER PHYSICS, SUPERCONDUCTIVITY AND SUPERFLUIDITY; ACETAMIDE; CALORIMETRY; CHEMICAL BONDS; CHLORIDES; DIFFERENTIAL THERMAL ANALYSIS; DIMERS; FOURIER TRANSFORMATION; INFRARED SPECTRA; LATTICE PARAMETERS; MONOCLINIC LATTICES; MONOCRYSTALS; SPECTROPHOTOMETRY; SYNTHESIS; THERMAL GRAVIMETRIC ANALYSIS; X-RAY DIFFRACTION

Citation Formats

Sharma, R., Nayak, P. S., Narayana, B., and Kant, R., E-mail: rkvk.paper11@gmail.com. Synthesis, characterization, crystal structure, and thermal analysis of 2-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) acetamide. United States: N. p., 2015. Web. doi:10.1134/S1063774515070226.
Sharma, R., Nayak, P. S., Narayana, B., & Kant, R., E-mail: rkvk.paper11@gmail.com. Synthesis, characterization, crystal structure, and thermal analysis of 2-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) acetamide. United States. doi:10.1134/S1063774515070226.
Sharma, R., Nayak, P. S., Narayana, B., and Kant, R., E-mail: rkvk.paper11@gmail.com. 2015. "Synthesis, characterization, crystal structure, and thermal analysis of 2-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) acetamide". United States. doi:10.1134/S1063774515070226.
@article{osti_22472044,
title = {Synthesis, characterization, crystal structure, and thermal analysis of 2-chloro-N-(1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) acetamide},
author = {Sharma, R. and Nayak, P. S. and Narayana, B. and Kant, R., E-mail: rkvk.paper11@gmail.com},
abstractNote = {The title compound, C{sub 13}H{sub 14}O{sub 2}N{sub 3}Cl, has been synthesized by the reaction of chloroacetyl chloride with 4-aminoantipyrine in basic media and characterized by FT-IR, CHN elemental analysis, UV-Vis, TGA, DTA, DSC and single crystal X-ray diffraction. crystals are monoclinic, sp. gr. P2{sub 1}/c, a = 6.9994(6), b = 12.4035(13), c = 15.836(2) Å, β = 100.367(9)°, Z = 4. The crystal structure is stabilized by N–H···O and C–H···O interactions, the former interactions result in the formation of dimers corresponding to R{sub 2}{sup 2} (10) graphset motif and the dimers are further connected by C–H···O hydrogen bonding forming chains. In addition, the thermal stability of the compound was determined by TGA, DTA, DSC analysis, and absorption at λ{sub max} = 298 nm was determined by UV-Vis spectrophotometer.},
doi = {10.1134/S1063774515070226},
journal = {Crystallography Reports},
number = 7,
volume = 60,
place = {United States},
year = 2015,
month =
}
  • The title compound N-(4-acetyl-5,5-dimethyl-4,5-dihydro-1,3,4-thiadiazol-2-yl)acetamide (III) was obtained from the reaction of 2-(propan-2-ylidene)hydrazinecarbothioamide (II) with acetic anhydride instead of formation of the desired thiosemcarbazide derivative of Meldrum acid. The structures of II and III were established by elemental analysis, IR, NMR, Mass and X-ray crystallographic studies. II crystallizes in triclinic system, sp. gr. P-bar1 Z = 2; III crystallizes in the monoclinic system, sp. gr. P2{sub 1}/c, Z = 8. Density functional theory (DFT) calculations have been carried out for III. {sup 1}H and {sup 13}C NMR of III has been calculated and correlated with experimental results.
  • Two oxazolines compound 1a and 1b, 2-[4(S)-4,5-dihydro-4-phenyl-2-ozazolinyl-benzenamine, and (C{sub 15}H{sub 14}N{sub 2}O), 2-[4(S)-4,5-dihydro-4-benzyl-2-ozazolinyl-benzenamine (C{sub 16}H{sub 16}N{sub 2}O) were obtained in moderate yield from the reactions of 2-aminobenzonitrile with optically active L-(+)-Phenylglycinol and L-(+)-Phenylalaninol, respectively, in chlorobenzene under dry, anaerobic conditions. ZnCl{sub 2} was dried under vacuum and acted as a Lewis acid catalyst in this reaction. The structures of 1a and 1b were determined by X-ray diffraction and NMR. There exist intra- and intermolecular N-H-N hydrogen bonds in the crystal structure.
  • We studied the extraction of trivalent Y, La, Pr, Nd, Sm, Eu, Gd, Dy, Er, and Lu from aqueous perchlorate solutions using a mixture of 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione (HBMPPT) and trioctylphosphine oxide (TOPO). The metal ion distribution coefficients (D-values) as a function of increasing lanthanide atomic number increased initially, reached a maximum value at Nd, then decreased to a nearly constant value for Gd and the later lanthanides. The D-values vary slightly across the lanthanide series, the maximum difference being a factor of 14 between La and Nd. Analysis of slopes of plots of log D versus pH, log [HBMPPT], and logmore » [TOPO] indicated that the stoichiometries of the extraction complexes varied across the lanthanide series showing a decrease in the number of HBMPPT (and/or BMPPT) units and an increase in the number of TOPO molecules involved in the major extraction species. This extraction system can provide a good way to separate the trivalent actinides from the trivalent lanthanides. 21 refs., 2 figs., 3 tabs.« less
  • The first measurements of distribution coefficients (k{sub d}) for Cm(III), Bk(III), Cf(III), Es(III), and Fm(III) between aqueous perchlorate solutions and solutions of 4-benzoyl-2,4-dihydro-5-methyl-2-phenyl-3H-pyrazol-3-thione (BMPPT) and the synergist tri-n-octylphosphine oxide (TOPO) in toluene are reported. Curium-243, berkelium-250, californium-249, einsteinium-254, and fermium-253 were used in these studies. The K{sub d} for {sup 241}Am was also measured and is in agreement with previously published results. Our new results show that the K{sub d}`s decrease gradually with increasing atomic number for the actinides with a dip at Cf. In general, the K{sub d}`s for these actinides are about about a factor of 10 greatermore » than the K{sub d}`s for the homologous lanthanides at a pH of 2.9, a BMPPT concentration of 0.2 M, and a TOPO concentration of 0.04 M. The larger K{sub d}`s for the actinides are consistent with greater covalent bonding between the actinide metal ion and the sulfur bonding site in the ligand. 9 refs., 2 figs., 1 tab.« less
  • The mechanism of the extraction of copper(II), nickel(II), cobalt(II) and thorium(IV) from aqueous buffer media with 4-dinitrobenzoyl1-2,4-dihydro-5-methy1-3H-pyrazol-3-one (DMPP) in benzene has been investigated. The values of log K where K refers to the extraction equilibrium Mn/sup +/ + nHL in equilibrium MLn + nH/sup +/ are Cu(II)(+0.3), Co(II)(-6.65), Ni(II)(-5.04) and Th(IV)(+6.1). Solid complexes synthesized have the composition CuL/sub 2/ x 2H/sub 2/O and ThL/sub 4/ respectively (L=anion of the ligand). DMPP seems to be superior to the corresponding 4-benzoyl and 4-nitrobenzoyl derivatives of 2,4-dihydro-5-methyl-2-phenyl1-3H-pyrazol-3-one (MPP) and also better than thenoyltrifluoroacetone, the popularly employed fluorinated ..beta..-diketone in the systems investigated. 2more » figures.« less