3880-50-0Relevant articles and documents
Synthesis and characterization of acetone hydrazones
Miro Sabate, Carles,Delalu, Henri
experimental part, p. 57 - 63 (2012/03/13)
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 ( 1H, 13C and 15N) 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, P21/n, Z = 4, a = 5.666(1) A, b = 6.254(1) A, c = 15.277(4) A, β = 91.30(2)°, V = 541.2(2) A3). 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. Copyright