Compound 26: Tris((4-(ethoxycarbonyl)-1H-pyrazol-5-yl)oxy)scandium

DOI: 10.14469/hpc/11714 Metadata

Created: 2022-11-05 15:10

Last modified: 2024-06-03 14:00

Author: Henry Rzepa

License: Creative Commons: Public Domain Dedication 1.0

Funding: (none given)

Description

Tris((4-(ethoxycarbonyl)-1H-pyrazol-5-yl)oxy)scandium (26): Sc(OTf)3 (143 mg, 0.290 mmol, 1.00 equiv) was added with stirring to pyrazolone 5 (136 mg, 0.871 mmol, 3.00 equiv) in EtOH (3.5 mL) at 79 °C. NaOMe (0.5 M in MeOH; 1.75 mL, 0.871 mmol, 3.00 equiv) was added and the mixture was heated at reflux for 15 h, after which the mixture was cooled to room temperature, H2O was added (20 mL), the precipitate was collected by filtration and dried in vacuo. Sc-pyrazolone complex 26 (125 mg, 0.240 mmol, 84%) 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 26. 1H-NMR (400 MHz, (CD3)2SO): δ (ppm) = 11.49 (s, 1H), 7.41 (s, 1H), 4.37 (t, J = 5.0 Hz, 1H), 4.12 (q, J = 7.1 Hz, 2H), 3.49 – 3.38 (m, 1H), 1.18 (t, J = 7.0 Hz, 4H), 1.05 (t, J = 7.0 Hz, 2H). 13C{1H}-NMR (101 MHz, (CD3)2SO): δ (ppm) = 166.3, 163.6, 149.6, 138.9, 92.2, 59.6, 56.1, 18.6, 14.4. IR (Diamond-ATR, neat) νmax (cm-1) = 3335, 1690, 1623, 1588, 1558, 1522, 1457, 1320, 1135, 1111, 932, 786, 775. HRMS (ES-ToF) m/z: [M + H]+ calc. for (C18H22N6O9Sc)+: 511.1002, found: 511.1014. m.p.: >275 °C (EtOH) (decomp.). Anal. Calcd for C18H21N6O9Sc ∙ Et2O: C, 45.21; H, 5.35; N, 14.38. Found: C, 45.51; H, 5.36; N, 13.34.

Files

FilenameSizeTypeDescription
26.cdxml 12KB chemical/x-cdxml Chemdraw connection table
26.png 40KB image/png Image representation
26.cdxml 11KB chemical/x-cdxml Chemdraw connection table v2
26.mol 3KB chemical/x-mdl-molfile MDL Molfile

Member of collection / collaboration

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

Subject Keywords

KeywordValue
inchi InChI=1S/3C6H8N2O3.Sc/c3*1-2-11-6(10)4-3-7-8-5(4)9;/h3*3H,2H2,1H3,(H2,7,8,9);/q;;;+3/p-3
inchikey LGDMWPFAARSMRW-UHFFFAOYSA-K
SMILES O=C(C1=C(O[Sc](OC2=C(C(OCC)=O)C=NN2)OC3=C(C(OCC)=O)C=NN3)NN=C1)OCC

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