Compound 20: bis(4-(ethoxycarbonyl)-1-phenyl-1H-pyrazol-5-olate) calcium

DOI: 10.14469/hpc/11347 Metadata

Created: 2022-10-09 18:51

Last modified: 2024-07-03 11:31

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 (Aqua)(ethanol) bis(4-(ethoxycarbonyl)-1-phenyl-1H-pyrazol-5-olate)calcium (20): CaCl2 (111 mg,1.00 mmol, 1.00 equiv) in H2O and EtOH (1 : 2; 3.0 mL) was added with stirring to pyrazolone 6 (464 mg, 2.00 mmol, 2.00 equiv) in EtOH (3.0 mL) at 79 °C. Aqueous NaOH (2 M; 1.0 mL, 2.00 mmol, 2.00 equiv) was added with stirring and the mixture was heated at reflux for 14 h, cooled to room temperature and the precipitate was collected by filtration and dried in vacuo. Ca-pyrazolone complex 20 (173 mg,0.305 mmol, 31%) 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 20. 1H-NMR (400 MHz, OC(CD3)2): δ (ppm) = 8.15 (d, J = 7.9 Hz, 4H), 7.54 (d, J = 1.0 Hz, 2H), 7.29 (t, J = 7.8 Hz, 4H), 7.05 (td, J = 7.4, 1.3 Hz, 2H), 4.23 – 4.13 (m, 4H), 3.57 (q, J = 7.0 Hz, 1H), 3.00 (s, 3H), 1.25 (td, J = 7.1, 1.0 Hz, 6H), 1.12 (td, J = 7.0, 1.0 Hz, 2H). 13C{1H}-NMR (101 MHz, OC(CD3)2): δ (ppm) = 168.6, 166.6, 141.9, 140.1, 129.0, 124.1, 119.7, 93.4, 59.8, 57.8, 19.2, 14.9. IR (Diamond-ATR, neat) νmax (cm-1) = 1653, 1599, 1565, 1543, 1523, 1498, 1420, 1372, 1357, 1325, 11227, 1204, 1081, 951, 751. m.p.: >270 °C (EtOH) (decomp.). Anal. Calcd for C24H22CaN4O6 ∙ 2 H2O ∙ EtOH: C, 53.42; H, 5.52; N, 9.58. Found: C, 53.02; H, 4.70; N, 9.74.

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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/11522 NMR Data for Compound 20.
10.14469/hpc/11521 IR Data for Compound 20.
10.14469/hpc/11348 Crystal data for Compound 20. (Aqua)(ethanol) bis(4-(ethoxycarbonyl)-1-phenyl-1H-pyrazol-5-olate)calcium

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