Synthesis and selected reactivity studies of a dissymmetric (phosphinoylmethylpyridine N-oxide) methylamine platform

Sabrina Ouizem, Sylvie L. Pailloux, Alisha D. Ray, Eileen N. Duesler, Diane A. Dickie, Robert T. Paine, Benjamin P. Hay

Research output: Contribution to journalArticlepeer-review

4 Scopus citations

Abstract

Efficient syntheses for the precursor molecules, 2-{6- [((diphenylphosphoryl)methyl)pyridin-2-yl]methyl}isoindoline-1,3-dione (2), 2-[(1,3-dioxoisoindolin-2-yl)methyl]-6-[(diphenylphosphoryl)methyl]pyridine 1-oxide (3), and their 6-[bis(2-(trifluoromethyl)phenyl)phosphoryl]methyl analogues are reported along with their transformations into the dissymmetric ligands, [(6-(aminomethyl)pyridin-2-yl)methyl]diphenylphosphine oxide (4), 2-(aminomethyl)-6-[(diphenylphosphoryl)methyl]pyridine 1-oxide (5) and 2-(aminomethyl)-6-{[bis(2-(trifluoromethyl)phenyl)phosphoryl]methyl}pyridine 1-oxide (5-F). Selected reactivity of the aminomethyl substituent of 4 and 5, as well as complexation reactions of several of the compounds with lanthanide(III) ions are described. Molecular structures of three uniquely different complexes, {Pr{2-[HC(O)N(H)CH2]-6-[Ph2P(O)CH2]C 5H3NO}(NO3)3(MeOH)}2, {Eu{2-[(Me2N)2CN(H+)CH2]-6-[Ph 2P(O)CH2]C5H3N(H) +}(NO3)4(OMe)} and {Er{2-[(C8H 4O2)NCH2]-6-[Ph2P(O)CH 2]C5H3N(O)}(NO3)3(MeOH)} ·(CH3)2CO, have been determined by single-crystal X-ray diffraction methods. The observed and computationally modeled structures that employ bidentate and tridentate ligand/metal interactions are compared. These results suggest further ligand modifications that should provide improved solvent extraction reagents.

Original languageEnglish (US)
Pages (from-to)3132-3148
Number of pages17
JournalEuropean Journal of Organic Chemistry
Volume2014
Issue number15
DOIs
StatePublished - May 2014

Keywords

  • Chelates
  • Lanthanides
  • Ligand design
  • N ligands
  • Nitrogen oxides

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