TY - JOUR
T1 - The structure of the compounds resulting from the reaction of arylhydrazines with dehydroacetic acid: an NMR and crystallographic study
AU - Kumar, Devinder
AU - Singh, Shiv P.
AU - Martínez, Ana
AU - Fruchier, Alain
AU - Elguero, José
AU - Martínez-Ripoll, Martín
AU - Carrió, Juan Server
AU - Virgili, Albert
PY - 1995/4/17
Y1 - 1995/4/17
N2 - The structure of the product obtained by reacting phenylhydrazine, p-chlorophenylhydrazine and hydrazine itself with dehydroacetic acid has been established by a combined use of X-ray crystallography and NMR (1H and 13C) spectroscopy. The X-ray structure of 1-phenyl-3-methyl-4(1-phenyl-3-methyl-1H-pyrazol-5-yl)-2H-3-pyrazolin-5-one1d has been determined. The compound crystallizes in the space group P21 a [C20H18N4O, a = 11.801(2), b = 7.911(1), c = 18.363(2) A, α = 90.00°, β = 100.04°, γ = 90.00°, Z = 4]. The structure corresponds to the NH-tautomer of the pyrazolinone moiety; the angle of twist corresponding to pyrazole rings, defined as C1-C2-C4-C5, is -119.1(7)°. NMR spectrum allows to estimate the tautomeric equilibrium constant in solution and in the solid state. The X-ray structure of compound 1 (NH-tautomer) was determined and compared with NMR results (solution and solid state). © 1995.
AB - The structure of the product obtained by reacting phenylhydrazine, p-chlorophenylhydrazine and hydrazine itself with dehydroacetic acid has been established by a combined use of X-ray crystallography and NMR (1H and 13C) spectroscopy. The X-ray structure of 1-phenyl-3-methyl-4(1-phenyl-3-methyl-1H-pyrazol-5-yl)-2H-3-pyrazolin-5-one1d has been determined. The compound crystallizes in the space group P21 a [C20H18N4O, a = 11.801(2), b = 7.911(1), c = 18.363(2) A, α = 90.00°, β = 100.04°, γ = 90.00°, Z = 4]. The structure corresponds to the NH-tautomer of the pyrazolinone moiety; the angle of twist corresponding to pyrazole rings, defined as C1-C2-C4-C5, is -119.1(7)°. NMR spectrum allows to estimate the tautomeric equilibrium constant in solution and in the solid state. The X-ray structure of compound 1 (NH-tautomer) was determined and compared with NMR results (solution and solid state). © 1995.
U2 - 10.1016/0040-4020(95)00172-5
DO - 10.1016/0040-4020(95)00172-5
M3 - Article
VL - 51
SP - 4891
EP - 4906
JO - Tetrahedron
JF - Tetrahedron
SN - 0040-4020
IS - 16
ER -