Synthesis and Coordination Properties of Trifluoromethyl Decorated Derivatives of 2,6-Bis[(diphenylphosphinoyl)methyl]pyridine N-Oxide Ligands with Lanthanide Ions

Sylvie Pailloux; C. E. Shirima; Alisha D. Ray; Eileen N. Duesler; Robert T. Paine; John R. Klaehn; Michael E. McIlwain; Benjamin P. Hay

doi:10.1021/ic802390c

Synthesis and Coordination Properties of Trifluoromethyl Decorated Derivatives of 2,6-Bis[(diphenylphosphinoyl)methyl]pyridine N-Oxide Ligands with Lanthanide Ions

Sylvie Pailloux, C. E. Shirima, Alisha D. Ray, Eileen N. Duesler, Robert T. Paine, John R. Klaehn, Michael E. McIlwain, Benjamin P. Hay

Chemistry (Twin Cities)

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Abstract

Phosphinoyl Grignard-based substitutions on 2,6-bis(chloromethyl)pyridine followed by N-oxidation of the intermediate 2,6-bis(phosphinoyl)methylpyridine compounds with mCPBA give the target trifunctional ligands 2,6-bis[bis(2- trifluoromethylphenyl)phosphinoylmethyl]pyridine 1-oxide (2a) and 2,6-bis[bis(3,5-bis(trifluoromethyl)phenyl)phosphinoylmethyl] pyridine 1-oxide (2b) in high yields. The ligands have been spectroscopically characterized, the molecular structures confirmed by single crystal X-ray diffraction methods, and the coordination chemistry surveyed with lanthanide nitrates. Single crystal X-ray diffraction analyses are described for the coordination complexes Nd(2a)(NO ₃) ₃, Nd(2a)(NO ₃) ₃ · (CH ₃CN) _0.5, Eu(2a)(NO ₃) ₃, and Nd(2b)(NO ₃) ₃ · (H ₂O) _1.25 in each case the ligand binds in a trident-ate mode to the Ln(III) cation. These structures are compared with the structures found for lanthanide coordination complexes of the parent NOPOPO ligand, [Ph ₂P(O)CH ₂] ₂C ₅H ₃NO.

Original language	English (US)
Pages (from-to)	3104-3113
Number of pages	10
Journal	Inorganic Chemistry
Volume	48
Issue number	7
DOIs	https://doi.org/10.1021/ic802390c
State	Published - Apr 17 2009

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title = "Synthesis and Coordination Properties of Trifluoromethyl Decorated Derivatives of 2,6-Bis[(diphenylphosphinoyl)methyl]pyridine N-Oxide Ligands with Lanthanide Ions",

abstract = "Phosphinoyl Grignard-based substitutions on 2,6-bis(chloromethyl)pyridine followed by N-oxidation of the intermediate 2,6-bis(phosphinoyl)methylpyridine compounds with mCPBA give the target trifunctional ligands 2,6-bis[bis(2- trifluoromethylphenyl)phosphinoylmethyl]pyridine 1-oxide (2a) and 2,6-bis[bis(3,5-bis(trifluoromethyl)phenyl)phosphinoylmethyl] pyridine 1-oxide (2b) in high yields. The ligands have been spectroscopically characterized, the molecular structures confirmed by single crystal X-ray diffraction methods, and the coordination chemistry surveyed with lanthanide nitrates. Single crystal X-ray diffraction analyses are described for the coordination complexes Nd(2a)(NO 3) 3, Nd(2a)(NO 3) 3 · (CH 3CN) 0.5, Eu(2a)(NO 3) 3, and Nd(2b)(NO 3) 3 · (H 2O) 1.25 in each case the ligand binds in a trident-ate mode to the Ln(III) cation. These structures are compared with the structures found for lanthanide coordination complexes of the parent NOPOPO ligand, [Ph 2P(O)CH 2] 2C 5H 3NO.",

author = "Sylvie Pailloux and Shirima, {C. E.} and Ray, {Alisha D.} and Duesler, {Eileen N.} and Paine, {Robert T.} and Klaehn, {John R.} and McIlwain, {Michael E.} and Hay, {Benjamin P.}",

year = "2009",

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doi = "10.1021/ic802390c",

language = "English (US)",

volume = "48",

pages = "3104--3113",

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T1 - Synthesis and Coordination Properties of Trifluoromethyl Decorated Derivatives of 2,6-Bis[(diphenylphosphinoyl)methyl]pyridine N-Oxide Ligands with Lanthanide Ions

AU - Pailloux, Sylvie

AU - Shirima, C. E.

AU - Ray, Alisha D.

AU - Duesler, Eileen N.

AU - Paine, Robert T.

AU - Klaehn, John R.

AU - McIlwain, Michael E.

AU - Hay, Benjamin P.

PY - 2009/4/17

Y1 - 2009/4/17

N2 - Phosphinoyl Grignard-based substitutions on 2,6-bis(chloromethyl)pyridine followed by N-oxidation of the intermediate 2,6-bis(phosphinoyl)methylpyridine compounds with mCPBA give the target trifunctional ligands 2,6-bis[bis(2- trifluoromethylphenyl)phosphinoylmethyl]pyridine 1-oxide (2a) and 2,6-bis[bis(3,5-bis(trifluoromethyl)phenyl)phosphinoylmethyl] pyridine 1-oxide (2b) in high yields. The ligands have been spectroscopically characterized, the molecular structures confirmed by single crystal X-ray diffraction methods, and the coordination chemistry surveyed with lanthanide nitrates. Single crystal X-ray diffraction analyses are described for the coordination complexes Nd(2a)(NO 3) 3, Nd(2a)(NO 3) 3 · (CH 3CN) 0.5, Eu(2a)(NO 3) 3, and Nd(2b)(NO 3) 3 · (H 2O) 1.25 in each case the ligand binds in a trident-ate mode to the Ln(III) cation. These structures are compared with the structures found for lanthanide coordination complexes of the parent NOPOPO ligand, [Ph 2P(O)CH 2] 2C 5H 3NO.

AB - Phosphinoyl Grignard-based substitutions on 2,6-bis(chloromethyl)pyridine followed by N-oxidation of the intermediate 2,6-bis(phosphinoyl)methylpyridine compounds with mCPBA give the target trifunctional ligands 2,6-bis[bis(2- trifluoromethylphenyl)phosphinoylmethyl]pyridine 1-oxide (2a) and 2,6-bis[bis(3,5-bis(trifluoromethyl)phenyl)phosphinoylmethyl] pyridine 1-oxide (2b) in high yields. The ligands have been spectroscopically characterized, the molecular structures confirmed by single crystal X-ray diffraction methods, and the coordination chemistry surveyed with lanthanide nitrates. Single crystal X-ray diffraction analyses are described for the coordination complexes Nd(2a)(NO 3) 3, Nd(2a)(NO 3) 3 · (CH 3CN) 0.5, Eu(2a)(NO 3) 3, and Nd(2b)(NO 3) 3 · (H 2O) 1.25 in each case the ligand binds in a trident-ate mode to the Ln(III) cation. These structures are compared with the structures found for lanthanide coordination complexes of the parent NOPOPO ligand, [Ph 2P(O)CH 2] 2C 5H 3NO.

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Synthesis and Coordination Properties of Trifluoromethyl Decorated Derivatives of 2,6-Bis[(diphenylphosphinoyl)methyl]pyridine N-Oxide Ligands with Lanthanide Ions

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