Spectroscopy, Crystal and Molecular Structures of New 4-Acylpyrazolone Dinitrophenylhydrazones

Still looking at the development of new materials with unique properties and taking advantage of the nucleophilic properties of amines to form stable azomethines, dinitrophenylhydrazine was reacted with 4-ethyl-5-methyl-2-phenyl-pyrazol-3-one and then with 4-propyl-5-methyl-2-phenyl-pyrazol-3-one to...

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Bibliographic Details
Published in:Crystals (Basel) 2016-10, Vol.6 (10), p.127-127
Main Authors: Idemudia, Omoruyi G, Hosten, Eric C
Format: Article
Language:English
Subjects:
acylpyrazolone
chemical shift
Condensation
Crystal structure
Crystals
Diffraction
dinitrophenylhydrazone
Imines
monoclinic
NMR spectroscopy
Schiff base
single crystal
Single crystals
spectroscopy
Tautomers
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Summary:Still looking at the development of new materials with unique properties and taking advantage of the nucleophilic properties of amines to form stable azomethines, dinitrophenylhydrazine was reacted with 4-ethyl-5-methyl-2-phenyl-pyrazol-3-one and then with 4-propyl-5-methyl-2-phenyl-pyrazol-3-one to get 4-ethyl-5-methyl-2-phenyl-pyrazol-3-one dinitrophenylhydrazone (Empp-Dh) and 4-propyl-5-methyl-2-phenyl-pyrazol-3-one dinitrophenylhydrazone (Pmpp-Dh), respectively, via a simple condensation reaction in a one-pot synthesis system. Careful interpretations of results from elemental analysis, mass and NMR spectroscopy were in agreement with single-crystal X-ray diffraction data. Reported Schiff bases in their single-crystal solid state exist in imine keto tautomer form, each crystallizing in a monoclinic crystal system, with a space group of C2/c (No. 15) in Empp-Dh and P21/c (No. 14) in Pmpp-Dh. They have extensive intra- and inter-molecular hydrogen as well as C-H***π-ring interactions.
ISSN:2073-4352
2073-4352
DOI:10.3390/cryst6100127