TY - JOUR
T1 - Cyclic and acyclic products from the reactions between methyl 3-oxobutanoate and arylhydrazines
AU - Wardell, James L.
AU - Skakle, Jan
AU - Low, John N.
AU - Glidewell, Christopher
PY - 2007/8
Y1 - 2007/8
N2 - The molecules of methyl 3-(2-nitrophenylhydrazono) butanoate, C11H13N3O4, (I), and methyl 3-(2,4-dinitrophenylhydrazono) butanoate, C11H12N4O6, ( II), both prepared from methyl 3- oxobutanoate and the corresponding nitrophenylhydrazine, exhibit polarized molecular electronic structures; in each of ( I) and ( II), the molecules are linked into chains by a single C - H center dot center dot center dot O hydrogen bond. The molecules of 5- hydroxy-3- methyl- 1- phenyl- 1H- pyrazole, C10H10N2O, ( III), prepared by the reaction of methyl 3- oxobutanoate and phenylhydrazine, are linked into chains by a single O - H center dot center dot center dot N hydrogen bond. The reaction between methyl 3- oxobutanoate and 3- nitrophenylhydrazine yields 5- hydroxy- 3- methyl- 1-( 3-nitrophenyl)- 1H- pyrazole, ( IV), which when crystallized from acetone yields 4- isopropylidene- 3- methyl- 1-( 3- nitrophenyl)1H- pyrazol- 5( 4H)- one, C13H13N3O3, ( V).
AB - The molecules of methyl 3-(2-nitrophenylhydrazono) butanoate, C11H13N3O4, (I), and methyl 3-(2,4-dinitrophenylhydrazono) butanoate, C11H12N4O6, ( II), both prepared from methyl 3- oxobutanoate and the corresponding nitrophenylhydrazine, exhibit polarized molecular electronic structures; in each of ( I) and ( II), the molecules are linked into chains by a single C - H center dot center dot center dot O hydrogen bond. The molecules of 5- hydroxy-3- methyl- 1- phenyl- 1H- pyrazole, C10H10N2O, ( III), prepared by the reaction of methyl 3- oxobutanoate and phenylhydrazine, are linked into chains by a single O - H center dot center dot center dot N hydrogen bond. The reaction between methyl 3- oxobutanoate and 3- nitrophenylhydrazine yields 5- hydroxy- 3- methyl- 1-( 3-nitrophenyl)- 1H- pyrazole, ( IV), which when crystallized from acetone yields 4- isopropylidene- 3- methyl- 1-( 3- nitrophenyl)1H- pyrazol- 5( 4H)- one, C13H13N3O3, ( V).
KW - supramolecular structures
KW - X-RAY
KW - hydrogen
KW - nitroanilines
KW - bond
KW - diffraction
U2 - 10.1107/S0108270107029447
DO - 10.1107/S0108270107029447
M3 - Article
SN - 0108-2701
VL - 63
JO - Acta Crystallographica Section C, Crystal Structure Communications
JF - Acta Crystallographica Section C, Crystal Structure Communications
ER -