Tuning amidoximate to enhance uranyl binding: A density functional theory study

Journal of Physical Chemistry A

Volumn 117, Issue 45, 2013, Pages 11558-11565

  Abney, Carter W ^a   Liu, Shubin ^b   Lin, Wenbin ^a  

^a UNIVERSITY OF CHICAGO   (United States)

^b UNIVERSITY OF NORTH CAROLINA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AVERAGE ERRORS; BINDING STRENGTH; DENSITY FUNCTIONAL THEORY STUDIES; ELECTRON DONATION; ELECTRONIC EFFECTS; FUNCTIONALIZED; HAMMETT CONSTANTS; THERMOCHEMICAL PROPERTIES;

DENSITY FUNCTIONAL THEORY; ELECTRONIC STRUCTURE; URANIUM ALLOYS; URANIUM COMPOUNDS;

URANIUM;

EID: 84887885013     PISSN: 10895639     EISSN: 15205215     Source Type: Journal    
DOI: 10.1021/jp408460x     Document Type: Article

References (48)

1. Davies, R. V.; Kennedy, J.; McIlroy, R. W.; Spence, R.; Hill, K. M. Extraction of Uranium from Sea Water Nature 1964, 203, 1110-1115
2. Kim, J.; Tsouris, C.; Mayes, R. T.; Oyola, Y.; Saito, T.; Janke, C. J.; Dai, S.; Schneider, E.; Sachde, D. Recovery of Uranium from Seawater: A Review of Current Status and Future Research Needs Sep. Sci. Technol. 2013, 48 (3) 367-387
3. Oguma, K.; Suzuki, T.; Saito, K. Determination of uranium in seawater by flow-injection preconcentration on dodecylamidoxime-impregnated resin and spectrophotometric detection Talanta 2011, 84 (5) 1209-1214
4. Schenk, H. J.; Astheimer, L.; Witte, E. G.; Schwochau, K. Development of Sorbers for the Recovery of Uranium from Seawater. 1. Assessment of Key Parameters and Screening Studies of Sorber Materials Sep. Sci. Technol. 1982, 17 (11) 1293-1308
5. Astheimer, L.; Schenk, H. J.; Witte, E. G.; Schwochau, K. Development of Sorbers for the Recovery of Uranium from Seawater. Part 2. The Accumulation of Uranium from Seawater by Resins Containing Amidoxime and Imidoxime Functional Groups Sep. Sci. Technol. 1983, 18 (4) 307-339
6. Seko, N.; Katakai, A.; Hasegawa, S.; Tamada, M.; Kasai, N.; Takeda, H.; Sugo, T.; Saito, K. Aquaculture of Uranium in Seawater by a Fabric-Adsorbent Submerged System Am. Nuc. Soc. 2003, 144 (2) 274-278
7. Seko, N.; Tamada, M.; Kasai, N.; Yoshii, F.; Simizu, T. Synthesis and Evaluation of Long Braid Adsorbent for Recovery of Uranium from Seawater Proc. Civil Eng. Ocean 2004, 20, 611-616
8. Goto, A.; Kusakabe, K.; Morooka, S.; Kago, T. A Test of Uranium Recovery from Seawater with a Packed Bed of Amidoxime Fiber Adsorbent Sep. Sci. Technol. 1993, 28 (6) 1273-1285
9. Kawai, T.; Saito, K.; Sugita, K.; Katakai, A.; Seko, N.; Sugo, T.; Kanno, J.-i.; Kawakami, T. Comparison of Amidoxime Adsorbents Prepared by Cografting Methacrylic Acid and 2-Hydroxyethyl Methacrylate with Acrylonitrile onto Polyethylene Ind. Eng. Chem. Res. 2000, 39 (8) 2910-2915
10. Takeda, T.; Saito, K.; Uezu, K.; Furusaki, S.; Sugo, T.; Okamoto, J. Adsorption and elution in hollow-fiber-packed bed for recovery of uranium from seawater Ind. Eng. Chem. Res. 1991, 30 (1) 185-190
11. Hirotsu, T.; Katoh, S.; Sugasaka, K.; Seno, M.; Itagaki, T. Binding ability of acetamide oxime with proton, copper(II), and dioxouranium(VI) in aqueous solutions J. Chem. Soc., Dalton Trans. 1986, 8, 1609-1611
12. Park, Y.-Y.; Kim, S.-Y.; Kim, J.-S.; Harada, M.; Tomiyasu, H.; Nogami, M.; Ikeda, Y. Complex Formation of U(VI) with Benzamidoxime in Non-aqueous Solvents J. Nucl. Sci. Technol. 2000, 37 (4) 344-348
13. Vukovic, S.; Watson, L. A.; Kang, S. O.; Custelcean, R.; Hay, B. P. How Amidoximate Binds the Uranyl Cation Inorg. Chem. 2012, 51 (6) 3855-3859
14. Barber, P. S.; Kelley, S. P.; Rogers, R. D. Highly selective extraction of the uranyl ion with hydrophobic amidoxime-functionalized ionic liquids via [small eta]2 coordination RSC Adv. 2012, 2 (22) 8526-8530
15. Tian, G.; Teat, S.; Zhang, Z.; Rao, L. Sequestering uranium from seawater: binding strength and modes of uranyl complexes with glutarimidedioxime Dalton. Trans. 2012, 41 (38) 11579-11586
16. Tian, G.; Teat, S.; Rao, L. Thermodynamic studies of U(VI) complexation with glutardiamidoxime for sequestration of uranium from seawater Dalton. Trans. 2013, 42 (16) 5690-5696
17. Xu, C.; Tian, G.; Teat, S. J.; Rao, L. Complexation of U(VI) with Dipicolinic Acid: Thermodynamics and Coordination Modes Inorg. Chem. 2013, 52 (5) 2750-2756
18. Vukovic, S.; Hay, B. P. De Novo Structure-Based Design of Bis-amidoxime Uranophiles Inorg. Chem. 2013, 52 (13) 7805-7810
19. Frisch, M. J. Gaussian 09; Gaussian, Inc.: Wallingford, CT, 2009.
20. Becke, A. D. Density-functional thermochemistry. III. The role of exact exchange J. Chem. Phys. 1993, 98 (7) 5648-5652
21. Lee, C.; Yang, W.; Parr, R. G. Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density Phys. Rev. B 1988, 37 (2) 785-789
22. Dolg, M.; Stoll, H.; Preuss, H.; Pitzer, R. M. Relativistic and correlation effects for element 105 (hahnium, Ha): a comparative study of M and MO (M = Nb, Ta, Ha) using energy-adjusted ab initio pseudopotentials J. Phys. Chem. 1993, 97 (22) 5852-5859
23. McLean, A. D.; Chandler, G. S. Contracted Gaussian-basis sets for molecular calculations. 2nd row atoms, Z=11-18 J. Chem. Phys. 1980, 72, 5639-5648
24. Raghavachari, K.; Binkley, J. S.; Seeger, R.; Pople, J. A. Self-consistent molecular orbital methods. Basis set for correlated wave-functions J. Chem. Phys. 1980, 72, 650-654
25. de Jong, W. A.; Aprà, E.; Windus, T. L.; Nichols, J. A.; Harrison, R. J.; Gutowski, K. E.; Dixon, D. A. Complexation of the Carbonate, Nitrate, and Acetate Anions with the Uranyl Dication: Density Functional Studies with Relativistic Effective Core Potentials J. Phys. Chem. A 2005, 109 (50) 11568-11577
26. Kang, S. O.; Vukovic, S.; Custelcean, R.; Hay, B. P. Cyclic Imide Dioximes: Formation and Hydrolytic Stability Ind. Eng. Chem. Res. 2012, 51 (19) 6619-6624
27. Wang, C. Z.; Lan, J. H.; Zhao, Y. L.; Chai, Z. F.; Wei, Y. Z.; Shi, W. Q. Density Functional Theory Studies of UO(2)(2+) and NpO(2)(+) Complexes with Carbamoylmethylphosphine Oxide Ligands Inorg Chem 2013, 52 (1) 196-203
28. Odoh, S. O.; Schreckenbach, G. DFT Study of Uranyl Peroxo Complexes with H2O, F-, OH-, CO32-, and NO3- Inorg. Chem. 2013, 52 (9) 5590-5602
29. Scalmani, G.; Frisch, M. J. Continuous surface charge polarizable continuum models of solvation J. Chem. Phys. 2010, 132, 114110-1-114110-15
30. Barone, V.; Cossi, M. Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model J. Phys. Chem. A 1998, 102, 1995-2001
31. Cossi, M.; Rega, N.; Scalmani, G.; Barone, V. Energies, structures, and electronic properties of molecules in solution with the C-PCM solvation model J. Comput. Chem. 2003, 24, 669-681
32. Shamov, G. A.; Schreckenbach, G. Density Functional Studies of Actinyl Aquo Complexes Studied Using Small-Core Effective Core Potentials and a Scalar Four-Component Relativistic Method J. Phys. Chem. A 2005, 109 (48) 10961-10974
33. Wiberg, K. B. Application of the pople-santry-segal CNDO method to the cyclopropylcarbinyl and cyclobutyl cation and to bicyclobutane Tetrahedron 1968, 24 (3) 1083-1096
34. Foster, J. P.; Weinhold, F. Natural hybrid orbitals J. Am. Chem. Soc. 1980, 102 (24) 7211-7218
35. Reed, A. E.; Weinstock, R. B.; Weinhold, F. Natural population analysis J. Chem. Phys. 1985, 83 (2) 735-746
36. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint Chem. Rev. 1988, 88 (6) 899-926
37. Gorelsky, S. I., AOMix program, v. 6.81. http://www.sg-chem.net.
38. Gorelsky, S. I.; Ghosh, S.; Solomon, E. I. Mechanism of N2O Reduction by the μ4-S Tetranuclear CuZ Cluster of Nitrous Oxide Reductase J. Am. Chem. Soc. 2005, 128 (1) 278-290
39. Allen, P. G.; Bucher, J. J.; Shuh, D. K.; Edelstein, N. M.; Reich, T. Investigation of Aquo and Chloro Complexes of UO22+, NpO2+, Np4+, and Pu3+ by X-ray Absorption Fine Structure Spectroscopy Inorg. Chem. 1997, 36 (21) 4676-4683
40. Hay, P. J.; Martin, R. L.; Schreckenbach, G. Theoretical Studies of the Properties and Solution Chemistry of AnO22+ and AnO2+ Aquo Complexes for An = U, Np, and Pu J. Phys. Chem. A 2000, 104 (26) 6259-6270
41. Denning, R. G. Electronic Structure and Bonding in Actinyl Ions and their Analogs J. Phys. Chem. A 2007, 111 (20) 4125-4143
42. Carboni, M.; Abney, C.; Liu, S.; Lin, W. Highly porous and stable metal-organic frameworks for uranium extraction Chem. Sci. 2013, 4 (6) 2396-2402
43. Hammett, L. P. The Effect of Structure upon the Reactions of Organic Compounds. Benzene Derivatives J. Am. Chem. Soc. 1937, 59 (1) 96-103
44. Kitaura, K.; Morokuma, K. A new energy decomposition scheme for molecular interactions within the Hartree-Fock approximation Int. J. Quantum Chem. 1976, 10 (2) 325-340
45. Ziegler, T.; Rauk, A. On the calculation of bonding energies by the Hartree Fock Slater method Theor. Chim. Acta 1977, 46 (1) 1-10
46. McClelland, R. A.; Roderick Fuller, J.; Esther Seaman, N.; Michael Rauth, A.; Battistella, R. 2-hydroxylaminoimidazoles-unstable intermediates in the reduction of 2-nitroimidazoles Biochem. Pharmacol. 1984, 33 (2) 303-309
47. Bolton, J. L.; McClelland, R. A. Kinetics and mechanism of the decomposition in aqueous solutions of 2-(hydroxyamino)imidazoles J. Am. Chem. Soc. 1989, 111 (21) 8172-8181
48. 2+ with amidoxime-related ligands: thermodynamics, kinetics, and structure; Oak Ridge National Laboratory: Oak Ridge, TN, 2013; pp 20-33.