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Synthesis and Spectral Correlation Study of some 3-(3,4-dichlorophenyl)-5-(Substituted Phenyl)-4,5-dihydro-1H-Pyrazole-1-yl-Ethanones

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Abstract:

Some N-acetyl pyrazoles including 3-(3,4-dichlorophenyl)-5-(substituted phenyl)-4,5-dihydro-1H-pyrazole-1-yl-ethanones have been synthesised by solvent free cyclization cum acetylation of chalcones including substituted styryl 3,4-dichlorophenyl ketones using hydrazine hydrate and acetic anhydride in presence of catalytic amount of fly-ash: H2SO4 catalyst. The yield of these N-acetyl pyrazole derivatives are more than 75%. The synthesised N-acetyl pyrazoline derivatives were characterized by their physical constants and spectral data. The infrared spectral νC=N and C=O (cm-1) frequencies, NMR chemical shifts (δ, ppm) of Ha, Hb, Hc, CH3 protons, C=N, C=O and CH3 carbons of 1-(3-(3,4-dichlorophenyl)-5-(substitutedphenyl)-4,5-dihydro-1H-pyrazole-1-yl) ethanones have been assigned and correlated with Hammett substituent constants and Swain-Lupton’s parameters using single and multi-regression analysis. From the results of statistical analyses the effect of substituents on the above group frequencies and chemical shifts of the acetylated pyrazoles were discussed.

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Periodical:
International Letters of Chemistry, Physics and Astronomy (Volume 19)
Pages:
44-57
Citation:
G. Thirunarayanan and K. Ravi, "Synthesis and Spectral Correlation Study of some 3-(3,4-dichlorophenyl)-5-(Substituted Phenyl)-4,5-dihydro-1H-Pyrazole-1-yl-Ethanones", International Letters of Chemistry, Physics and Astronomy, Vol. 19, pp. 44-57, 2013
Online since:
October 2013
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