Crystal and molecular structure and vibrational spectra of 2,6-bis(diphenylphosphorylmethyl)-4-methylphenol and its complex with cerium(III) nitrate

Матвеева, А. Г.; Starikova, Z. A.; Matrosov, E. I.; Бодрин, Г. В.; Матвеев, С. В.; Нифантьев, Э. Е.

doi:10.1134/s0036023606020136

Cited by 6 publications

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“…16,17 Unlike these compounds, molecules L 2 in the crystalline state contain a strong intramolecular O-H...O=P hydrogen bond (X ray diffraction data), which is retained in solu tion (IR spectroscopic data). 9 The 31 P and 1 H NMR spectroscopic data (see Table 1), which remain virtually unchanged upon dilution (solu tions in dichloromethane, chloroform, acetone, and DMSO), are also consistent with the proposed structure.…”

Section: Resultssupporting

confidence: 77%

“…The yellow crystalline precipitate that formed was separated, washed with a 1 : 4 benzene-hexane mixture, and dried at 140 °C in vacuo (1)(2) 3 • •(Me 2 CO)] (2b) was prepared by the reaction of equimolar amounts of ligand L 2 and the salt Ce(NO 3 ) 3 •6H 2 O according to a procedure described earlier. 9 The characteristics of 2b corre The white precipitate that formed was filtered off, washed with anhydrous diethyl ether, and dried at room temperature in vacuo (1 Torr). Complex 3a was obtained in a yield of 0.1416 g (65%).…”

Section: Methodsmentioning

confidence: 99%

“…Mod els of Ce III complexes were constructed with the use of the corresponding polyhedra and the Ce...O(C) and Ce...O(P) co ordination bond lengths (2.66 Å and 2.41 Å, respectively), which were calculated by averaging the bond lengths determined by X ray diffraction analysis in the present study and those pub lished earlier. 9 The strain energy of the conformation (∆E) was estimated as the difference between the calculated energies of this conformer and the conformer corresponding to the global minimum.…”

Section: Methodsmentioning

confidence: 99%

“…Complexes with L 2 of composition Ln(L 2 )(NO 3 ) 3 •nSolv, where Solv is the sol vent molecule (water or acetone), are readily formed in solvents of different polarity with the use of the reagents in a ratio of 1 : 1. Earlier, 9 we have studied and structur ally characterized the [Ce(L 2 )(NO 3 ) 3 •Me 2 CO] com plex (2b). In this complex, the neutral phenol molecule is tridentately coordinated.…”

Section: Complexationmentioning

confidence: 99%

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Coordination chemistry of 2,6-bis(diphenylphosphorylmethyl)-4-methylphenol

et al. 2005

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The trifunctional ligand, 2,6 bis(diphenylphosphorylmethyl) 4 methylphenol (L 2 ), forms complexes with cerium(III) nitrate having a ligand to metal ratio of 1 : 1, 2 : 1, and 3 : 1. The structures of these complexes in the solid state and in solution were studied by X ray diffrac tion, IR and NMR ( 1 H and 31 P) spectroscopy, and conformational analysis (molecular me chanics). The 2 : 1 complexes of L 2 with lanthanum(III) and neodymium(III) nitrates were synthesized and characterized. In all complexes, the neutral ligand is coordinated through both phosphoryl oxygen atoms. The hydroxy oxygen atom is coordinated only in some complexes, and the hydrogen atom of the hydroxy group is involved in hydrogen bonding. The composi tions and structures of the resulting complexes depend on the method of synthesis and the nature of solvent. The ligand was found to undergo easy inner sphere oxidation. The structure of one of the transformation products was established by X ray diffraction. Unlike the coordi nated ligand, the free ligand is very stable to oxidation.Bis and polyphosphoryl compounds containing an aromatic moiety and the phosphorylmethyl groups in the ortho and meta positions of the benzene ring are conve nient extractants for separation of transuranium and rare earth metals from aqueous solutions of nitric acid. 1-6 In particular, reagents L 1 containing substituents in the meta positions exhibit high separation factors ( f ) with respect to the Eu III /Am III pair. However, the absolute partition coefficients D = [M] org /[M] aq are small. R = Ar, Alk, AlkOModified ligand L 2 containing an additional coordi nating center in the second position of the benzene ring would be expected to exhibit the coordination and extrac tion properties analogous to those of L 1 , because the main ligand contour remains unchanged. At the same time, additional coordination of the phenolic OH group should increase stability of the extracted complexes and, conse quently, increase the extraction coefficients with reten tion of the selectivity level typical of L 1 , because the phos phoryl groups will remain the main coordinating centers. Actually, already our first experiments on extraction of U VI , Am III , and Eu III from aqueous solutions of nitric acid with solutions of L 2 in dichloroethane have showed 7 that the efficiency of extraction (D) increases by an order of magnitude compared to that of the prototype, viz., dioxide L 1 (R = Ph), the separation factor of the met als ( f ) remaining the same (more detailed data will be published elsewhere).Coordination chemistry of ligand L 2 is poorly known. Only two 1 : 1 complexes with erbium 8 and cerium 9 ni trates were characterized.In the present study, the coordination ability of L 2 was studied using complexation with cerium(III) nitrate as an example. The 2 : 1 complexes with neodymium(III) and lanthanum(III) nitrates were examined in less detail. Here, we report only data necessary for comparison. Since the resulting complexes are unstable during storage, we stud ied also the...

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Section: Resultssupporting

confidence: 77%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Section: Complexationmentioning

confidence: 99%

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Coordination chemistry of 2,6-bis(diphenylphosphorylmethyl)-4-methylphenol

et al. 2005

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“…The literature shows few examples in which a phenol group is combined with other coordinating group, such as amines, which has greater affinity to metal cations, forming a polydentate ligand . Although usually phenols does not form strong coordination complexes, in these cases the accompanying donor group facilitates the participation of a phenol to the coordination of the metal cation.…”

Section: Introductionmentioning

confidence: 99%

Effect of the Pyridine Substituent on the Role of the Phenol Functional Group in [Cu(pOHBz)₂(dPy)₂] Complexes (pOHBz: p‐Hydroxybenzoate, dPy= 4‐Phenylpyridine, 4‐Benzylpyridine, 3‐Phenylpyridine).

et al. 2017

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The crystal structure of three new complexes of stoichiometry [Cu(pOHBz)2(dPy)2] (pOHBz: p‐hydroxybenzoate, dPy= 4‐phenylpyridine, 4‐benzylpyridine, 3‐phenylpyridine) and its comparison with the previously reported [Cu(pOHBz)2(Py)2] (1) indicate that the nature and position of the pyridine substituent determines different roles for the phenol group from the pOHBz ligand and, consequently, the coordination number and geometry of Cu(II) centers. Results herein reported show the versatility of the pOHBz ligand towards the coordination of Cu(II). Different carboxylate bonding modes are also observed: monodentate, bidentate chelating or bidentate bridge. Besides, this governs the different roles of the phenol group of the pOHBz ligand: founding of supramolecular hydrogen‐bond based network or direct bonding to the copper cation, yielding 2D coordination polymers.

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Seven‐Membered Intramolecular Hydrogen Bonding of Phenols: Database Analysis and Phloroglucinol Model Compounds

Castellano

Homan

et al. 2012

Eur J Org Chem

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Seven‐membered intramolecular hydrogen bonding (7MHB) arrangements involving phenolic hydroxyl group donors have been investigated through Cambridge Structural Database (CSD) and literature mining, and by the characterization of model compounds. The CSD reveals the numerous H‐bond accepting functional groups that can participate in 7MHB when they are proximal to a phenolic OH, including alcohols, amides, amines, ethers, N‐containing heterocycles, ketones, N‐oxides, phosphates, and phosphane oxides. The HB contacts are defined by Ophenol···N and Ophenol···O distances of ca. 2.7 Å, and two dihedral angles that fall within the range of typical peptide γ‐turns. Two of the identified 7MHB motifs have been readily mapped onto the phloroglucinol (1,3,5‐trihydroxybenzene) scaffold to provide eight model compounds; intramolecular hydrogen bonding involving all three hydroxyl groups is shown to persist in solution and the solid state for the compounds. Intramolecular 7MHB enforces nonplanar conformations that should be useful when designing molecular hosts and catalysts.

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Crystal and molecular structure and vibrational spectra of 2,6-bis(diphenylphosphorylmethyl)-4-methylphenol and its complex with cerium(III) nitrate

Cited by 6 publications

References 11 publications

Coordination chemistry of 2,6-bis(diphenylphosphorylmethyl)-4-methylphenol

Coordination chemistry of 2,6-bis(diphenylphosphorylmethyl)-4-methylphenol

Effect of the Pyridine Substituent on the Role of the Phenol Functional Group in [Cu(pOHBz)₂(dPy)₂] Complexes (pOHBz: p‐Hydroxybenzoate, dPy= 4‐Phenylpyridine, 4‐Benzylpyridine, 3‐Phenylpyridine).

Seven‐Membered Intramolecular Hydrogen Bonding of Phenols: Database Analysis and Phloroglucinol Model Compounds

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Crystal and molecular structure and vibrational spectra of 2,6-bis(diphenylphosphorylmethyl)-4-methylphenol and its complex with cerium(III) nitrate

Cited by 6 publications

References 11 publications

Coordination chemistry of 2,6-bis(diphenylphosphorylmethyl)-4-methylphenol

Coordination chemistry of 2,6-bis(diphenylphosphorylmethyl)-4-methylphenol

Effect of the Pyridine Substituent on the Role of the Phenol Functional Group in [Cu(pOHBz)2(dPy)2] Complexes (pOHBz: p‐Hydroxybenzoate, dPy= 4‐Phenylpyridine, 4‐Benzylpyridine, 3‐Phenylpyridine).

Seven‐Membered Intramolecular Hydrogen Bonding of Phenols: Database Analysis and Phloroglucinol Model Compounds

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Effect of the Pyridine Substituent on the Role of the Phenol Functional Group in [Cu(pOHBz)₂(dPy)₂] Complexes (pOHBz: p‐Hydroxybenzoate, dPy= 4‐Phenylpyridine, 4‐Benzylpyridine, 3‐Phenylpyridine).