Crystal structure of the growth inhibitor, ‘maleic hydrazide’(1,2-dihydropyridazine-3,6-dione)

Abstract

The crystal structure of the title compound (I) has been determined by symbolic-addition and rotation-function procedures and refined by full-matrix least-squares methods to R 0.063 for 568 observed reflections. Crystals are triclinic, space group P i , with Z = 2 in a cell of dimensions a = 5.83(2), b = 5.78(2), c = 7.31 (2) 8, a = 79.0(3), p = 99.5(3)", y = 107.2(3)". Analysis of the molecular structure suggests that maleic hydrazide could act as a pyrimidine or a purine analogue.

2-Phenyl-4-hydroxyphthalazin-1-one: A Benzoannelated Derivative of Maleic Hydrazide

“…We ®nd similar differences between computed and measured values for maleic hydrazide: 0.058 A Ê at the HF/6-31G* level and 0.034 A Ê at the B3LYP/6-31G* level. Thus, allowance for electron correlation increases the computed C O bond length, Katrusiak (1993) and are between 1/5 and 1/3 of those given for the triclinic polymorph (Cradwick, 1976). More realistic s.u.…”

“…Occurrence of the lactim±lactam tautomer (II) in both the solid state and in solution is favoured by all the evidence: the crystal structures of triclinic (Cradwick, 1976) and monoclinic (Katrusiak, 1993) maleic hydrazide, and dichloromaleic hydrazide (Ottersen, 1973); IR spectroscopy of maleic hydrazide in the vapour phase (Rodionova & Levin, 1967) and in the crystal (Mashima, 1962; polymorph not speci®ed); 1 H broad-line NMR, IR and Raman spectroscopies (all in the solid state, but the polymorph not speci®ed; Lippert et al, 1975); NMR studies of maleic hydrazide and derivatives in dimethyl sulfoxide solution (Katritzky & Waring, 1964;Ohashi et al, 1964); UV spectroscopy of aqueous solutions (Barlin, 1974); other physico-chemical evidence is summarized by Katritzky & Lagowski (1963;see pp. 366±368).…”

A Theoretical Survey of Solvation Effects on Tautomerism Stability of Maleic Hydrazide

“…www.orientjchem.org Key words: Maleic hydrazide, Tautomer, PCM model, NBO Charge poly-morphs [13][14][15][16][17][18] and, in all the polymorphs, MH adopts exclusively the oxo-hydroxy form (Scheme 1). Tautomerism of solid maleic hydrazide was studied experimentally using infrared 19,20 and Raman spectroscopies.…”

Polymorphism and phase transitions in maleic hydrazide

“…There are now many reported applications including sensors, medical diagnostics and phase transfer agents. [1] Use in polymerisation catalysis for a variety of chemical systems has, however, only recently gained attention with mixed success. [2][3][4][5][6] This paper focuses on our discoveries with early transition metal (primarily vanadium) oxo or organoimido fragments supported on the hexahomotrioxacalix [3]arene ligand (see figure for an example) or by one of a range of new tripodal ligands.…”

“…The structural work has been undertaken using both laboratorybased conventional X-ray sources and synchrotron radiation at Daresbury Laboratory, all at low temperature. Maleic hydrazide (MH) was reported to crystallize in three polymorphic forms, one triclinic (MH1) [1], and two monoclinic ones (MH2 and MH3) [2,3]. The crystal structures of these polymorphs are built of OH--O and NH--O bonded aggregates.…”