Synthesis, selected coordination chemistry and extraction behavior of a (phosphinoylmethyl)pyridyl N-oxide-functionalized ligand based upon a 1,4-diazepane platform
Abstract
For syntheses of new multidentate chelating ligands ((6,6'4(1,4-diazepane-1,4-diyl)bis(methylene))bis(pyridine-6,2-diyl))bis(methylene))bis(diphenylphosphine oxide) (2) and 6,6'-((1,4-diazepane1,4-diyl)bis(methylene))bis(2-((diphenylphosphoryl)methyl)pyridine 1-oxide) (3), based upon a 1,4-diazepane platform functionalized with 2-(diphenylphosphinoylmethyl)pyridine P-oxide and 2-(diphenylphosphinoylmethyl)pyridine NP-dioxide fragments, respectively, the results are reported. Our results from studies of the coordination chemistry of the ligands with selected lanthanide nitrates and Cu(BF4)(2) are outlined, and crystal structures for two complexes, [Cu(2)](BF4)2 and [Cu(3)](BF4)2, are described along with survey Eu(III) and Am(III) solvent extraction analysis, for 3.
- Authors:
-
- Univ. of New Mexico, Albuquerque, NM (United States)
- Univ. of Hawaii, Honolulu, HI (United States)
- Bruker AXS Inc., Madison, WI (United States)
- Supramolecular Design Inst., Oak Ridge, TN (United States)
- Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)
- Publication Date:
- Research Org.:
- Oak Ridge National Laboratory (ORNL), Oak Ridge, TN (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)
- OSTI Identifier:
- 1261469
- Alternate Identifier(s):
- OSTI ID: 1249607
- Grant/Contract Number:
- AC05-00OR22725; FG02-03ER15419; CHE-0443580
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Polyhedron
- Additional Journal Information:
- Journal Volume: 97; Journal Issue: C; Journal ID: ISSN 0277-5387
- Publisher:
- Elsevier
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY; Diazepane; Pyridyl; Phosphine oxide; Coordination chemistry; X-ray crystal structures; MM3 FORCE-FIELD; MOLECULAR-MECHANICS; CRYSTAL-STRUCTURE; COPPER(II) COMPLEXES; DECORATED PYRIDINE; SOLVENT-EXTRACTION; N; P; P'-TRIOXIDE; LANTHANIDE; THERMODYNAMICS; AMERI
Citation Formats
Ouizem, Sabrina, Rosario Amorin, Daniel, Dickie, Diane A., Cramer, Roger E., Campana, Charles F., Hay, Benjamin P., Podair, Julien, Delmau, Laetitia H., and Paine, Robert T. Synthesis, selected coordination chemistry and extraction behavior of a (phosphinoylmethyl)pyridyl N-oxide-functionalized ligand based upon a 1,4-diazepane platform. United States: N. p., 2015.
Web. doi:10.1016/j.poly.2015.05.006.
Ouizem, Sabrina, Rosario Amorin, Daniel, Dickie, Diane A., Cramer, Roger E., Campana, Charles F., Hay, Benjamin P., Podair, Julien, Delmau, Laetitia H., & Paine, Robert T. Synthesis, selected coordination chemistry and extraction behavior of a (phosphinoylmethyl)pyridyl N-oxide-functionalized ligand based upon a 1,4-diazepane platform. United States. https://doi.org/10.1016/j.poly.2015.05.006
Ouizem, Sabrina, Rosario Amorin, Daniel, Dickie, Diane A., Cramer, Roger E., Campana, Charles F., Hay, Benjamin P., Podair, Julien, Delmau, Laetitia H., and Paine, Robert T. Sat .
"Synthesis, selected coordination chemistry and extraction behavior of a (phosphinoylmethyl)pyridyl N-oxide-functionalized ligand based upon a 1,4-diazepane platform". United States. https://doi.org/10.1016/j.poly.2015.05.006. https://www.osti.gov/servlets/purl/1261469.
@article{osti_1261469,
title = {Synthesis, selected coordination chemistry and extraction behavior of a (phosphinoylmethyl)pyridyl N-oxide-functionalized ligand based upon a 1,4-diazepane platform},
author = {Ouizem, Sabrina and Rosario Amorin, Daniel and Dickie, Diane A. and Cramer, Roger E. and Campana, Charles F. and Hay, Benjamin P. and Podair, Julien and Delmau, Laetitia H. and Paine, Robert T.},
abstractNote = {For syntheses of new multidentate chelating ligands ((6,6'4(1,4-diazepane-1,4-diyl)bis(methylene))bis(pyridine-6,2-diyl))bis(methylene))bis(diphenylphosphine oxide) (2) and 6,6'-((1,4-diazepane1,4-diyl)bis(methylene))bis(2-((diphenylphosphoryl)methyl)pyridine 1-oxide) (3), based upon a 1,4-diazepane platform functionalized with 2-(diphenylphosphinoylmethyl)pyridine P-oxide and 2-(diphenylphosphinoylmethyl)pyridine NP-dioxide fragments, respectively, the results are reported. Our results from studies of the coordination chemistry of the ligands with selected lanthanide nitrates and Cu(BF4)(2) are outlined, and crystal structures for two complexes, [Cu(2)](BF4)2 and [Cu(3)](BF4)2, are described along with survey Eu(III) and Am(III) solvent extraction analysis, for 3.},
doi = {10.1016/j.poly.2015.05.006},
journal = {Polyhedron},
number = C,
volume = 97,
place = {United States},
year = {Sat May 09 00:00:00 EDT 2015},
month = {Sat May 09 00:00:00 EDT 2015}
}
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Figures / Tables:
Table 1.: Crystallographic Data for 1a, [Cu(2)](BF4)2 and [Cu(3)](BF4)2
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Works referenced in this record:
Complexation and Separation of Lanthanides(III) and Actinides(III) by Heterocyclic N-Donors in Solutions
journal, October 2008
- Kolarik, Zdenek
- Chemical Reviews, Vol. 108, Issue 10
Separation of long-lived radionuclides from high active nuclear waste
journal, September 2002
- Madic, Charles; Lecomte, Michaël; Baron, Pascal
- Comptes Rendus Physique, Vol. 3, Issue 7-8
Multicoordinate ligands for actinide/lanthanide separations
journal, January 2007
- Dam, Henk H.; Reinhoudt, David N.; Verboom, Willem
- Chem. Soc. Rev., Vol. 36, Issue 2
Chemistry of Diglycolamides: Promising Extractants for Actinide Partitioning
journal, November 2011
- Ansari, Seraj A.; Pathak, Priyanath; Mohapatra, Prasanta K.
- Chemical Reviews, Vol. 112, Issue 3
Aqueous Partitioning of Minor Actinides by Different Processes
journal, February 2011
- Ansari, Seraj A.; Pathak, Priyanath; Mohapatra, Prashanta K.
- Separation & Purification Reviews, Vol. 40, Issue 1
Clean separation technologies of rare earth resources in China
journal, April 2013
- Liao, Chunsheng; Wu, Sheng; Cheng, Fuxiang
- Journal of Rare Earths, Vol. 31, Issue 4
Chelating properties of 2-((diphenylphosphino)methyl)pyridine N,P-dioxide and 2,6-bis((diphenylphosphino)methyl)pyridine N,P,P'-trioxide toward f-element ions
journal, May 1993
- Rapko, B. M.; Duesler, E. N.; Smith, P. H.
- Inorganic Chemistry, Vol. 32, Issue 10
Synthesis and molecular structures of complexes of bismuth(III) nitrate with tridentate ligands : 2,6-BIS(-CH2 P((O)R2) substituted pyridine-N-oxides
journal, August 1995
- Engelhardt, U.; Rapko, B. M.; Duesler, E. N.
- Polyhedron, Vol. 14, Issue 17-18
Coordination chemistry and extraction properties of phosphonopyridyl N,P oxides
journal, June 1998
- Bond, E. M.; Gan, X.; Fitzpatrick, J. R.
- Journal of Alloys and Compounds, Vol. 271-273
Synthesis and Molecular Structure of a Plutonium(IV) Coordination Complex: [Pu(NO 3 ) 2 {2,6-[(C 6 H 5 ) 2 P(O)CH 2 ] 2 C 5 H 3 NO} 2 ](NO 3 ) 2 •1.5H 2 O•0.5MeOH
journal, September 2000
- Bond, Evelyn M.; Duesler, Eileen N.; Paine, Robert T.
- Inorganic Chemistry, Vol. 39, Issue 18
Isolation and structure of a europium(III) chloride complex of 2,6-bis[(diphenylphosphino)methyl]pyridine N,P,P′-trioxide
journal, October 2000
- Bond, E. M.; Duesler, E. N.; Paine, R. T.
- Polyhedron, Vol. 19, Issue 20-21
Synthesis, Characterization, and Coordination Chemistry of a New Geometrically Hindered Trifunctional Ligand, 4,5-Bis(diphenylphosphino)- sym -octahydroacridine N , P , P ‘-Trioxide
journal, October 2000
- Gan, Xin-Min; Parveen, Sahrah; Smith, Wayne L.
- Inorganic Chemistry, Vol. 39, Issue 20
Synthesis and crystal structure of a ten-coordinate plutonium(iv) ion complexed by 2-[(diphenylphosphino)methyl]pyridine N,P-dioxide: [Pu(NO3)3{2-[(C6H5)2P(O)CH2]C5H4NO}2][Pu(NO3)6]0.5
journal, April 2002
- Matonic, John H.; Neu, Mary P.; Enriquez, Alejandro E.
- Journal of the Chemical Society, Dalton Transactions, Issue 11
Synthesis and Coordination Properties of New Bis(phosphinomethyl)pyridine N , P , P ‘-Trioxides
journal, August 2001
- Gan, Xin-Min; Duesler, Eileen N.; Paine, Robert T.
- Inorganic Chemistry, Vol. 40, Issue 17
Synthesis and Coordination Properties of 1-(Diphenylphosphine oxide)-1-(2‘-pyridyl N -oxide)-3-(diphenylphosphine oxide)propane
journal, January 2002
- Paine, Robert T.; Bond, Evelyn M.; Parveen, S.
- Inorganic Chemistry, Vol. 41, Issue 2
Synthesis and coordination chemistry of arene soluble 4-alkyl-2,6-bis[(diphenylphosphino)methyl]pyridine N,P,P′-trioxide ligands
journal, January 2003
- Gan, Xin-Min; T. Paine, Robert; Duesler, Eileen N.
- Dalton Trans., Issue 1
The synthesis and lanthanide coordination chemistry of 2,6-bis[(dicyclohexyl)phosphino-methyl]pyridine N,P,P′-trioxide
journal, March 2005
- Gan, Xinmin; Rapko, Brian M.; Duesler, Eileen N.
- Polyhedron, Vol. 24, Issue 4
Synthesis and Coordination Properties of Trifluoromethyl Decorated Derivatives of 2,6-Bis[(diphenylphosphinoyl)methyl]pyridine N-Oxide Ligands with Lanthanide Ions
journal, February 2009
- Pailloux, Sylvie; Shirima, Cornel Edicome; Ray, Alisha D.
- Inorganic Chemistry, Vol. 48, Issue 7
Synthesis and lanthanide coordination chemistry of trifluoromethyl derivatives of phosphinoylmethyl pyridine N-oxides
journal, January 2009
- Pailloux, Sylvie; Shirima, Cornel Edicome; Ray, Alisha D.
- Dalton Transactions, Issue 36
THE SOLVENT EXTRACTION OF AMERICIUM(III) IN HNO 3 SOLUTIONS BY 2,6-BIS[(DIPHENYIJHOSPHINO) METHYL]PYRIDINE N,P,P′ TRIOXIDE
journal, May 1997
- Bond, Evelyn M.; Engelhardt, Udo; Deere, Timothy P.
- Solvent Extraction and Ion Exchange, Vol. 15, Issue 3
THE SOLVENT EXTRACTION OF AMERICIUM(III) IN HCl SOLUTIONS BY 2,6-BIS[(DIPHENYLPHOSPHINO)METHYL]PYRIDINE N,P,P'- TRIOXIDE
journal, July 1998
- Bond, Evelyn M.; Engelhardt, Udo; Deere, Timothy P.
- Solvent Extraction and Ion Exchange, Vol. 16, Issue 4
Features of the Thermodynamics of Two-Phase Distribution Reactions of Americium(III) and Europium(III) Nitrates into Solutions of 2,6-Bis[(bis(2-ethylhexyl)phosphino)methyl]pyridine N , P , P ‘-Trioxide
journal, November 2002
- Nash, Kenneth L.; Lavallette, Claire; Borkowski, Marian
- Inorganic Chemistry, Vol. 41, Issue 22
Synthesis of a tetradentate piperazine ligand and a structural study of its coordination compounds
journal, July 1999
- Ratilainen, Jari; Airola, Karri; Fröhlich, Roland
- Polyhedron, Vol. 18, Issue 17
Copper(II) Complexes of Pyridyl-Appended Diazacycloalkanes: Synthesis, Characterization, and Application to Catalytic Olefin Aziridination
journal, September 2000
- Halfen, Jason A.; Uhan, Joseph M.; Fox, Derek C.
- Inorganic Chemistry, Vol. 39, Issue 21
Novel Iron(III) Complexes of Sterically Hindered 4N Ligands: Regioselectivity in Biomimetic Extradiol Cleavage of Catechols
journal, July 2008
- Mayilmurugan, Ramasamy; Stoeckli-Evans, Helen; Palaniandavar, Mallayan
- Inorganic Chemistry, Vol. 47, Issue 15
Synthesis of aluminium complexes bearing a piperazine-based ligand system
journal, January 2010
- Johnstone, Nick C.; Aazam, Elham S.; Hitchcock, Peter B.
- Journal of Organometallic Chemistry, Vol. 695, Issue 2
Effect of the chelate ring size on the cleavage activity of DNA by copper(II) complexes containing pyridyl groups
journal, April 2013
- Massoud, Salah S.; Perkins, Richard S.; Knierim, Kathleen D.
- Inorganica Chimica Acta, Vol. 399
Synthesis and spectroscopic characterization of dicyanamido–Cu(II) complexes. Part 2: Crystal structure of the complexes of tris[2-(2-pyridylethyl)]amine, tris(2-pyridylmethyl)amine and 1,4-bis[2-(2-pyridylethyl)]piperazine
journal, October 2008
- Mautner, Franz A.; Soileau, Jesse B.; Bankole, Paul K.
- Journal of Molecular Structure, Vol. 889, Issue 1-3
Iron(II) Complexes of Two Amine/Imine N 5 Chelate Ligands Containing a 1,4-Diazepane Core - To Crossover or Not To Crossover
journal, January 2013
- Schmidt, Marc; Wiedemann, Dennis; Moubaraki, Boujemaa
- European Journal of Inorganic Chemistry, Vol. 2013, Issue 5-6
Manganese(II) complexes of pyridyl-appended diazacyclo-alkanes: Effect of ligand backbone ring size on catalytic olefin oxidation
journal, April 2012
- Saravanan, Natarajan; Palaniandavar, Mallayan
- Inorganica Chimica Acta, Vol. 385
Coordination chemistry of heterocycle-functionalized diazamesocycles: tuning the productive NiII complexes through altering the pendants of ligands
journal, March 2005
- Guo, Ya-Mei; Du, Miao; Bu, Xian-He
- Inorganica Chimica Acta, Vol. 358, Issue 6, p. 1887-1896
[Gd-AAZTA] - : A New Structural Entry for an Improved Generation of MRI Contrast Agents
journal, November 2004
- Aime, Silvio; Calabi, Luisella; Cavallotti, Camilla
- Inorganic Chemistry, Vol. 43, Issue 24
Variation of water exchange dynamics with ligand structure and stereochemistry in lanthanide complexes based on 1,4-diazepine derivatives
journal, January 2009
- Elemento, Elisa M.; Parker, David; Aime, Silvio
- Organic & Biomolecular Chemistry, Vol. 7, Issue 6
Synthesis and comparative anion binding profiles of two di-aqua Eu(iii) complexes
journal, January 2010
- Imperio, Daniela; Giovenzana, Giovanni B.; Law, Ga-lai
- Dalton Transactions, Vol. 39, Issue 41
Preparation, crystallographic and theoretical study on a bifunctional Gd-AAZTA derivative as potential MRI contrast agent precursor
journal, October 2013
- Artali, R.; Bombieri, G.; Giovenzana, G. B.
- Inorganica Chimica Acta, Vol. 407
BYPASS: an effective method for the refinement of crystal structures containing disordered solvent regions
journal, March 1990
- van der Sluis, P.; Spek, A. L.
- Acta Crystallographica Section A Foundations of Crystallography, Vol. 46, Issue 3
Molecular mechanics. The MM3 force field for hydrocarbons. 1
journal, November 1989
- Allinger, Norman L.; Yuh, Young H.; Lii, Jenn Huei
- Journal of the American Chemical Society, Vol. 111, Issue 23
Molecular mechanics. The MM3 force field for hydrocarbons. 2. Vibrational frequencies and thermodynamics
journal, November 1989
- Lii, Jenn Huei; Allinger, Norman L.
- Journal of the American Chemical Society, Vol. 111, Issue 23
Molecular mechanics. The MM3 force field for hydrocarbons. 3. The van der Waals' potentials and crystal data for aliphatic and aromatic hydrocarbons
journal, November 1989
- Lii, Jenn Huei; Allinger, Norman L.
- Journal of the American Chemical Society, Vol. 111, Issue 23
Methods for molecular mechanics modeling of coordination compounds
journal, July 1993
- Hay, Benjamin P.
- Coordination Chemistry Reviews, Vol. 126, Issue 1-2
Conformational equilibria in six-membered rings
journal, January 1979
- Niemeyer, Hermann M.
- Journal of Molecular Structure, Vol. 57
Open-chain polyamine ligands with more rigid double connecting bridges. Study of their metal ion selectivities by molecular mechanics calculation, crystallography, and thermodynamics
journal, January 1990
- Hancock, Robert D.; Ngwenya, M. Patrick; Evers, Ann
- Inorganic Chemistry, Vol. 29, Issue 2
Complexation of N4-Tetradentate Ligands with Nd(III) and Am(III)
journal, December 2012
- Ogden, Mark D.; Sinkov, Serguei I.; Meier, G. Patrick
- Journal of Solution Chemistry, Vol. 41, Issue 12
Search for Improved Host Architectures: Application of de Novo Structure-Based Design and High-Throughput Screening Methods To Identify Optimal Building Blocks for Multidentate Ethers
journal, December 2005
- Hay, Benjamin P.; Oliferenko, Alexander A.; Uddin, Jamal
- Journal of the American Chemical Society, Vol. 127, Issue 48
Structural design principles for self-assembled coordination polygons and polyhedra
journal, January 2013
- Young, Neil J.; Hay, Benjamin P.
- Chem. Commun., Vol. 49, Issue 14
Synthesis and Coordination Chemistry of Phosphine Oxide Decorated Dibenzofuran Platforms
journal, June 2012
- Rosario-Amorin, Daniel; Duesler, Eileen N.; Paine, Robert T.
- Inorganic Chemistry, Vol. 51, Issue 12
Synthesis and Properties of New (Phosphinoylmethyl)Pyridine N-Oxides
journal, April 2013
- Pailloux, Sylvie L.; Rosario-Amorin, Daniel; Chakravarty, Manab
- Zeitschrift für anorganische und allgemeine Chemie, Vol. 639, Issue 7
Synthesis, Lanthanide Coordination Chemistry, and Liquid–Liquid Extraction Performance of CMPO-Decorated Pyridine and Pyridine N -Oxide Platforms
journal, March 2013
- Rosario-Amorin, Daniel; Ouizem, Sabrina; Dickie, Diane A.
- Inorganic Chemistry, Vol. 52, Issue 6
Synthesis and f-element ligation properties of N CMPO-decorated pyridine N-oxide platforms
journal, January 2014
- Ouizem, Sabrina; Rosario-Amorin, Daniel; Dickie, Diane A.
- Dalton Trans., Vol. 43, Issue 22
Synthesis and Selected Reactivity Studies of a Dissymmetric (Phosphinoylmethylpyridine N -Oxide) Methylamine Platform: A (Phosphinoylmethyl Pyridine N -Oxide) Methyl Amine Platform
journal, April 2014
- Ouizem, Sabrina; Pailloux, Sylvie L.; Ray, Alisha D.
- European Journal of Organic Chemistry, Vol. 2014, Issue 15
The Cambridge Structural Database: a quarter of a million crystal structures and rising
journal, May 2002
- Allen, Frank H.
- Acta Crystallographica Section B Structural Science, Vol. 58, Issue 3
Di-, Tri-, Tetra-, and Hexanuclear Copper(II) Mono-organophosphates: Structure and Nuclearity Dependence on the Choice of Phosphorus Substituents and Auxiliary N-Donor Ligands
journal, December 2008
- Murugavel, Ramaswamy; Kuppuswamy, Subramaniam; Maity, Amarendra Nath
- Inorganic Chemistry, Vol. 48, Issue 1
Works referencing / citing this record:
Ligands for f-element extraction used in the nuclear fuel cycle
journal, January 2017
- Leoncini, Andrea; Huskens, Jurriaan; Verboom, Willem
- Chemical Society Reviews, Vol. 46, Issue 23
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