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Synthesis and Characterization of Acetone Hydrazones
Author(s) -
Miró Sabaté Carles,
Delalu Henri
Publication year - 2012
Publication title -
zeitschrift für anorganische und allgemeine chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.354
H-Index - 66
eISSN - 1521-3749
pISSN - 0044-2313
DOI - 10.1002/zaac.201100400
Subject(s) - chemistry , monoclinic crystal system , anhydrous , acetone , infrared spectroscopy , raman spectroscopy , hydrazone , mass spectrometry , crystal structure , methylhydrazine , spectroscopy , elemental analysis , natural bond orbital , crystallography , inorganic chemistry , molecule , organic chemistry , chromatography , physics , quantum mechanics , optics , phenylhydrazine
1‐Isopropylidene‐2‐methylhydrazine ( 1 ), 1‐isopropylidene‐2‐hydroxyethylhydrazine ( 2 ) and 1‐isopropylidene‐2‐formylhydrazine ( 3 ) were synthesized by reaction of the corresponding hydrazine with an excess of acetone in the presence of a drying agent (anhydrous sodium sulfate or barium oxide). All compounds 1 – 3 were characterized by elemental analysis, coupled gas chromatography‐mass spectrometry (GC–MS), multinuclear NMR spectroscopy ( 1 H, 13 C and 15 N) and vibrational spectroscopy (infrared and Raman). Compounds 1 and 2 are liquid at room conditions and their density was measured by means of a picnometer, however, (at room conditions) compound 3 is a solid and its crystal density and structure were determined by low temperature X‐ray diffraction techniques (monoclinic, P 2 1 / n , Z = 4, a = 5.666(1) Å, b = 6.254(1) Å, c = 15.277(4) Å, β = 91.30(2)°, V = 541.2(2) Å 3 ). The structure of hydrazone 3 is discussed in detail and compared to that of monoformylhydrazine. Finally, the (gas phase) structure of compound 3 was optimized using DFT calculations (B3LYP/6‐31+G(d, p)) and its NBO charges are reported.