Acidity of the amidoxime functional group in aqueous solution: A combined experimental and computational study

Journal of Physical Chemistry B

Volumn 119, Issue 8, 2015, Pages 3567-3576

  Mehio, Nada ^a   Lashely, Mark A ^b   Nugent, Joseph W ^b   Tucker, Lyndsay ^b   Correia, Bruna ^b   Do Thanh, Chi Linh ^a   Dai, Sheng ^a,c   Hancock, Robert D ^b   Bryantsev, Vyacheslav S ^c  

^a UNIVERSITY OF TENNESSEE   (United States)

^b UNIVERSITY OF NORTH CAROLINA WILMINGTON   (United States)

^c OAK RIDGE NATIONAL LABORATORY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPUTATION THEORY; SOLVENTS; URANIUM; URANIUM COMPOUNDS;

AMIDOXIME; BINDING CONSTANT; COMPUTATIONAL STUDIES; FUTURE GENERATIONS; OXO-ACIDS; ROOT MEAN SQUARE DEVIATIONS; SEVERAL PROTOCOLS; SOLVENT EFFECTS;

FUNCTIONAL GROUPS;

EID: 84923901995     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp512778x     Document Type: Article

References (66)

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. Saito, K.; Miyauchi, T. Chemical Forms of Uranium in Aritifical Seawater J. Nucl. Sci. Technol. 1982, 19, 145-150
3. Choppin, G. R. Soluble Rare Earth and Actinide Species in Seawater Mar. Chem. 1989, 28, 19-26
4. 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. 2012, 48 (3) 367-387
5. 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
6. 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, 307-339
7. Sodaye, H.; Nisan, S.; Poletiko, C.; Prabhakar, S.; Tewari, P. K. Extraction of Uranium from the Concentrated Brine Rejected by Integrated Nuclear Desalination Plants Desalination 2009, 235 (1-3) 9-32
8. Kawai, T.; Saito, K.; Sugita, K.; Katakai, A.; Seko, N.; Sugo, T.; Kawakami, T.; Kanno, J. Comparison of Amidoxime Adsorbents Prepared by Cografting Methacrylic Acid and 2-Hydroxyethyl Methacrylate with Acrylonitrile onto Polyethylene Ind. Eng. Res. Chem. 2000, 39, 2910-2915
9. Kawai, T.; Saito, K.; Sugita, K.; Kawakami, T.; Kanno, J.; Katakai, A.; Seko, N.; Sugo, T. Preparation of Hydrophilic Amidoxime Fibers by Cografting Acrylonitrile and Methacrylic Acid from an Optimized Monomer Composition Radiat. Phys. Chem. 2000, 59, 405-411
10. 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
11. Hay, B. P.; Chagnes, A.; Cote, A. G. On the Metal Ion Selectivity of Oxoacid Extractants Solvent Extr. Ion Exch. 2013, 31, 95-105
12. Dürüst, N.; Akay, M. A.; Dürüst, Y.; Kiliç, E. Protonation Constants of Some N-Substituted Amidoximes in a 50% Ethanol-Water Mixture (v/v) Anal. Sci. 2001, 16, 825-827
13. 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
14. Bunton, C. A.; Nelson, S. E.; Quan, C. Micellar Effects Upon Dephosphorylation by Amidoximes J. Org. Chem. 1982, 47, 1157-1160
15. Aubort, J. D.; Hudson, R. F. Enhanced reactivity of nucleophiles: orbital symmetry and the so-called "[small alpha]-effect" J. Chem. Soc. D: Chem. Commun. 1970, 15, 937-938
16. Simanenko, Y. S.; Prokopeva, T. M.; Belousova, I. A.; Popov, A. F.; Karpichev, E. A. Amidoximes as Effective Acceptors of Acyl Group Theor. Exp. Chem. 2001, 37, 288-295
17. Hohenberg, P.; Kohn, W. Inhomogeneous Electron Gas Phys. Rev. 1964, 136, B864-B871
18. Kohn, W.; Sham, L. J. Self-Consistent Equations Including Exchange and Correlation Effects Phys. Rev. 1965, 140, A1133-A1138
19. Møller, C.; Plesset, M. S. Note on an Approximation Treatment for Many-Electron Systems Phys. Rev. 1934, 46, 618-22
20. Head-Gordon, M.; Pople, J. A.; Frisch, M. J. MP2 Energy Evaluation by Direct Methods Chem. Phys. Lett. 1988, 153, 503-506
21. Purvis, G. D.; Bartlett, R. J. A Full Coupled-Cluster Singles and Doubles Model: The Inclusion of Disconnected Triples J. Chem. Phys. 1982, 76, 1910-1918
22. Raghavachari, K.; Trucks, G. W.; Pople, J. A.; Head-Gordon, M. A Fifth-Order Perturbation Comparison of Electron Correlation Theories Chem. Phys. Lett. 1989, 157, 479-483
23. Watts, J. D.; Gauss, J.; Bartlett, R. J. Coupled-Cluster Methods with Noniterative Triple Excitations for Restricted Open-Shell Hartree-Fock and Other General Single Determinant Reference Functions. Energies and Analytical Gradients J. Chem. Phys. 1993, 98, 8718-8733
24. Zhao, Y.; Truhlar, D. G. The M06 Suite of Density Functionals for Main Group Thermochemistry, Thermochemical Kinetics, Noncovalent Interactions, Excited States, and Transition Elements: Two New Functionals and Systematic Testing of Four M06-Class Functionals and 12 Other Functionals Theor. Chem. Acc. 2008, 120, 215-241
25. Marenich, A. V.; Cramer, C. J.; Truhlar, D. G. Universal Solvation Model Based on Solute Electron Density and a Continuum Model of the Solvent Defined by the Bulk Dielectric Constant and Atomic Surface Tensions J. Phys. Chem. B 2009, 113, 6378-6396
26. Kovács, D.; Wölfling, J.; Szabó, N.; Szécsi, M.; Kovács, I.; Zupkó, I.; Frank, é. An Efficient Approach to Novel 17-5′-(1′,2′,4′)-Oxadiazolyl Androstenes via the Cyclodehydration of Cytotoxic O-Steroidacylamidoximes, and an Evaluation of Their Inhibitory Action on 17α-Hydroxylase/C17,20-Lyase Eur. J. Med. Chem. 2013, 70, 649-660
27. García-álvarez, R.; Díaz-álvarez, A. E.; Borge, J.; Crochet, P.; Cadierno, V. Ruthenium-Catalyzed Rearrangement of Aldoximes to Primary Amides in Water Organometallics 2012, 31, 6482-6490
28. Billo, E. J. EXCEL for Chemists, 2 nd ed.; Wiley-CH: New York, 2001.
29. a Calculations of Aliphatic C-H Acids in Dimethyl Sulfoxide Chem. Phys. Lett. 2013, 558, 42-47
30. a Calculations of Aliphatic Amines, Diamines, and Aminoamides via Density Functional Theory with a Poisson-Boltzmann Continuum Solvent Model J. Phys. Chem. A 2007, 111, 4422-4430
31. Kelly, C. P.; Cramer, C. J.; Truhlar, D. G. Aqueous Solvation Free Energies of Ions and Ion-Water Clusters Based on an Accurate Value for the Absolute Aqueous Solvation Free Energy of the Proton J. Phys. Chem. B 2006, 110, 16066-16081
32. Frisch, M. J.; Gaussian 09 Revision D.01; Gaussian, Inc.: Wallingford, CT, 2009.
33. Valiev, M. NWChem: A Comprehensive and Scalable Open-Source Solution for Large Scale Molecular Simulations Comput. Phys. Commun. 2010, 181, 1477-1489
34. Becke, A. D. Density-Functional Thermochemistry. III. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
35. 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, 785-789
36. Andersson, M. P.; Uvdal, P. New Scale Factors for Harmonic Vibrational Frequencies Using the B3LYP Density Functional Method with the Triple-χ Basis Set 6-311+G(d,p) J. Phys. Chem. A 2005, 109, 2937-2941
37. Koch, H.; Fernández, B.; Christiansen, O. The Benzene-Argon Complex: A Ground and Excited State Ab Initio Study J. Chem. Phys. 1998, 108, 2784-2790
38. Cancès, E.; Mennucci, B.; Tomasi, J. A New Integral Equation Formalism for the Polarizable Continuum Model: Theoretical Background and Applications to Isotropic and Anisotropic Dielectrics J. Chem. Phys. 1997, 107, 3032-3041
39. Mennucci, B.; Cancès, E.; Tomasi, J. Evaluation of Solvent Effects in Isotropic and Anisotropic Dielectrics and in Ionic Solutions with a Unified Integral Equation Method: Theoretical Bases, Computational Implementation, and Numerical Applications J. Phys. Chem. B 1997, 101 (49) 10506-10517
40. Cancès, E.; Mennucci, B. New Applications of Integral Equations Methods for Solvation Continuum Models: Ionic Solutions and Liquid Crystals J. Mater. Chem. 1998, 23, 309-326
41. 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
42. 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
43. Klamt, A.; Schuurmann, G. COSMO: A New Approach to Dielectric Screening in Solvents with Explicit Expressions for the Screening Energy and Its Gradient J. Chem. Soc. Perkin Trans. 2 1993, 5) 799-805
44. Chipman, D. M. Charge Penetration in Dielectric Models of Solvation J. Chem. Phys. 1997, 106, 10194-10206
45. Zhan, C.-G.; Bentley, J.; Chipman, D. M. Volume Polarization in Reaction Field Theory J. Chem. Phys. 1998, 108, 177-192
46. Chipman, D. M. New Formulation and Implementation for Volume Polarization in Dielectric Continuum Theory J. Chem. Phys. 2006, 124, 224111
47. Schmidt, M. W. General Atomic and Molecular Electronic Structure System J. Comput. Chem. 1993, 14, 1347-1363
48. Martell, A. E.; Hancock, R. D. Metal Complexes in Aqueous Solutions. Plenum Press: New York, 1996.
49. Tsukube, H.; F., Hiroyuki; Odani, A.; Takeda, Y.; Kudo, Y.; Inoue, Y.; Liu, Y.; Sakamoto, H.; Kimura, K. Determination of Stability Constants. In Comprehensive Supramolecular Chemistry, Lehn, J. M.; Atwood, J. L.; Davis, J. E. D.; MacNicol, D. D.; Vogtle, F., Eds.; Pergamon: New York, 1996; Vol. 8.
50. 2 Mixed Oxides and Their Relationship to Catalyst Activities for 1-Butene Isomerization J. Catal. 1995, 157, 244-258
51. Hancock, R. D. Molecular Mechanics Calculations and Metal Ion Recognition Acc. Chem. Res. 1990, 23, 253-257
52. Zhao, Y.; Truhlar, D. G. A new local density functional for main-group thermochemistry, transition metal bonding, thermochemical kinetics, and noncovalent interactions J. Chem. Phys. 2006, 125, 194101
53. NIST Chemistry Webbook. NIST: Gaithersburg, MD, 2005. http://webbook.nist. gov/chemistry/.
54. Bryantsev, V. S.; Diallo, M. S.; van Duin, A. C. T.; Goddard, W. A. Evaluation of B3LYP, X3LYP, and M06-Class Density Functionals for Predicting the Binding Energies of Neutral, Protonated, and Deprotonated Water Clusters J. Chem. Theory Comput. 2009, 5, 1016-1026
55. Smith, R. M.; Martell, A. E. Critical Stability Constants. Plenum Press: New York, 1981.
56. a Scale J. Phys. Chem. A 2003, 107, 9380-9386
57. Eckert, F.; Leito, I.; Kaljurand, I.; Kütt, A.; Klamt, A.; Diedenhofen, M. Prediction of acidity in acetonitrile solution with COSMO-RS J. Comput. Chem. 2009, 30, 799-810
58. a Calculations for Carboxylic Acids Using Complete Basis Set and Gaussian-n Models Combined with CPCM Continuum Solvation Methods J. Am. Chem. Soc. 2001, 123, 7314-7319
59. a Determinations for Substituted Phenols J. Am. Chem. Soc. 2002, 124, 6421-6427
60. a Values; CRC Press: Boca Raton, FL, 2013; p 175.
61. Amado, A. M.; Fiuza, S. M.; Batista de Carvalho, L. A. E.; Ribeiro-Claro, P. J. A. On the Effects of Changing Gaussian Program Version and SCRF Defining Parameter: Isopropylamine as a Case Study Bull. Chem. Soc. Jpn. 2012, 85, 962-975
62. Cramer, C. J. Essentials of Computational Chemistry: Theories and Models, 2 nd ed.; John Wiley & Sons Ltd.: Chichester, West Sussex, England, 2004.
63. Barone, V.; Cossi, M.; Tomasi, J. A New Definition of Cavities for the Computation of Solvation Free Energies by the Polarizable Continuum Model J. Chem. Phys. 1997, 107, 3210
64. Marenich, A. V.; Ding, W.-D.; Cramer, C. J.; Truhlar, D. G. Resolution of a Challenge for Solvation Modeling: Calculation of Dicarboxylic Acid Dissociation Constants Using Mixed Discrete-Continum Solvation Models J. Phys. Chem. Lett. 2012, 3, 1437-1442
65. Pliego, J. R., Jr.; Riveros, J. M. The Cluster-Continuum Model for the Calculation of the Solvation Free Energy of Ionic Species J. Phys. Chem. A 2001, 105, 7241-7247
66. Abney, C. W.; Liu, S.; Lin, W.-B. Tuning Amidoximate to Enhance Uranyl Binding: A Density Functional Theory Study J. Phys. Chem. A 2013, 117, 11558-11565