Compound 16: bis(4-(ethoxycarbonyl)-1-phenyl-1H-pyrazol-5-olate)magnesium

DOI: 10.14469/hpc/11335 Metadata

Created: 2022-10-09 10:47

Last modified: 2024-11-22 13:50

Author: Henry Rzepa

License: Creative Commons: Public Domain Dedication 1.0

Funding: (none given)

Description

1H and 13C primary NMR, IR and crystal data for Bis(ethanol) bis(4-(ethoxycarbonyl)-1-phenyl-1H-pyrazol-5-olate)magnesium (16): MgCl2 (48.0 mg,0.499 mmol, 1.00 equiv) in EtOH and H2O (1 : 1; 2.0 mL) was added with stirring to pyrazolone 6 (232 mg, 0.999 mmol, 2.00 equiv) in EtOH (3.0 mL) at 79 °C. Aqueous NaOH (2 M; 0.5 mL, 0.999 mmol, 2.00 equiv) was added with stirring and the mixture was heated at reflux for 15 h, after which the mixture was cooled to room temperature, the precipitate was collected by filtration and dried in vacuo. Mg-pyrazolone complex 16 (205 mg, 0.354 mmol, 71%) was obtained as a white solid, essentially pure by its 1H NMR spectrum. Crystals suitable for X-ray crystallography were obtained by slow evaporation from an EtOH solution of complex 16. 1H-NMR (400 MHz, OC(CD3)2): δ (ppm) = 8.15 (d, J = 8.1 Hz, 2H), 7.57 (s, 1H), 7.33 (t, J = 7.8 Hz, 2H), 7.10 (t, J = 7.4 Hz, 1H), 4.24 (q, J = 7.1 Hz, 2H), 3.63 – 3.53 (m, 2H), 1.28 (t, J = 7.1 Hz, 3H), 1.12 (t, J = 7.0 Hz, 2H). 13C{1H}-NMR (101 MHz, OC(CD3)2): δ (ppm) = 170.0, 166.9, 141.6, 139.6, 129.1, 124.6, 119.8, 93.1, 60.6, 58.5, 18.9, 14.8. IR (Diamond-ATR, neat) νmax (cm-1) = 1680, 1647, 1599, 1566, 1527, 1499, 1465, 1457, 1420, 1360, 1331, 1231, 1208, 1081, 948, 784, 752. m.p.: 273 – 277 °C (EtOH). Anal. Calcd for C24H22MgN4O6 ∙ 2 EtOH ∙ H2O: C, 56.34; H, 6.08; N, 9.39. Found: C, 56.11; H, 5.39; N, 9.65.

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DOIDescription
10.14469/hpc/10386 Syntheses and Characterization of Main Group, Transition Metal, Lanthanide and Actinide Complexes of Bidentate Acylpyrazolone Ligands

Members

DOIDescription
10.14469/hpc/11691 Compound 16: bis(4-(ethoxycarbonyl)-1-phenyl-1H-pyrazol-5-olate)magnesium. NMR and IR prediction, G = -2107.704571
10.14469/hpc/11542 NMR Data for Compound 16.
10.14469/hpc/11543 IR data for Compound 16.
10.14469/hpc/11336 Primary crystal structure data for compound 16 Bis(ethanol) bis(4-(ethoxycarbonyl)-1-phenyl-1H-pyrazol-5-olate)magnesium

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