Electrostatic potential within the free volume space of imidazole-based solvents: Insights into gas absorption selectivity

Journal of Physical Chemistry B

Volumn 118, Issue 1, 2014, Pages 255-264

  Liu, Haining ^a   Zhang, Zhongtao ^a   Bara, Jason E ^a   Turner, C Heath ^a  

^a University of Alabama   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION SELECTIVITIES; DIRECT CALCULATION; ELECTROSTATIC POTENTIAL CALCULATION; ELECTROSTATIC POTENTIALS; MOLECULAR SIMULATIONS; SELECTIVE ABSORPTION; TEMPERATURE RANGE; VOLUME CAVITIES;

CARBON DIOXIDE; ELECTROSTATICS; ETHERS; FREE VOLUME; GAS ABSORPTION; LIGHT ABSORPTION; SOLVENTS;

PLANTS (BOTANY);

EID: 84892584402     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/jp410143j     Document Type: Article

References (73)

1. 2 J. Phys. Chem. Lett. 2010, 1, 3478-3479
2. 2 So Soluble in Imidazolium-Based Ionic Liquids? J. Am. Chem. Soc. 2004, 126, 5300-5308
3. Lopes, J.; Padua, A. A. H. Nanostructural Organization in Ionic Liquids J. Phys. Chem. B 2006, 110, 3330-3335
4. DelPopolo, M. G.; Voth, G. A. On the Structure and Dynamics of Ionic Liquids J. Phys. Chem. B 2004, 108, 1744-1752
5. Liu, Z. P.; Huang, S. P.; Wang, W. C. A Refined Force Field for Molecular Simulation of Imidazolium-Based Ionic Liquids J. Phys. Chem. B 2004, 108, 12978-12989
6. Urahata, S. M.; Ribeiro, M. C. C. Structure of Ionic Liquids of 1-Alkyl-3-Methylimidazolium Cations: A Systematic Computer Simulation Study J. Chem. Phys. 2004, 120, 1855-1863
7. - J. Am. Chem. Soc. 2005, 127, 17842-17851
8. Margulis, C. J.; Stern, H. A.; Berne, B. J. Computer Simulation of a "Green Chemistry" Room-Temperature Ionic Solvent J. Phys. Chem. B 2002, 106, 12017-12021
9. Yan, T. Y.; Burnham, C. J.; Del Popolo, M. G.; Voth, G. A. Molecular Dynamics Simulation of Ionic Liquids: The Effect of Electronic Polarizability J. Phys. Chem. B 2004, 108, 11877-11881
10. Shah, J. K.; Brennecke, J. F.; Maginn, E. J. Thermodynamic Properties of the Ionic Liquid 1- n -Butyl-3-Methylimidazolium Hexafluorophosphate from Monte Carlo Simulations Green Chem. 2002, 4, 112-118
11. Hanke, C. G.; Atamas, N. A.; Lynden-Bell, R. M. Solvation of Small Molecules in Imidazolium Ionic Liquids: A Simulation Study Green Chem. 2002, 4, 107-111
12. Lynden-Bell, R. M.; Del Popolo, M. G.; Youngs, T. G. A.; Kohanoff, J.; Hanke, C. G.; Harper, J. B.; Pinilla, C. C. Simulations of Ionic Liquids, Solutions, and Surfaces Acc. Chem. Res. 2007, 40, 1138-1145
13. Cadena, C.; Zhao, Q.; Snurr, R. Q.; Maginn, E. J. Molecular Modeling and Experimental Studies of the Thermodynamic and Transport Properties of Pyridinium-Based Ionic Liquids J. Phys. Chem. B 2006, 110, 2821-2832
14. Shah, J. K.; Maginn, E. J. Monte Carlo Simulations of Gas Solubility in the Ionic Liquid 1- n -Butyl-3-Methylimidazolium Hexafluorophosphate J. Phys. Chem. B 2005, 109, 10395-10405
15. Maginn, E. J. Molecular Simulation of Ionic Liquids: Current Status and Future Opportunities J. Phys.: Condens. Matter 2009, 21, 373101-1-373101-17
16. Borodin, O.; Smith, G. D. Structure and Dynamics of n -Methyl- n -Propylpyrrolidinium Bis(Trifluoromethanesulfonyl)Imide Ionic Liquid from Molecular Dynamics Simulations J. Phys. Chem. B 2006, 110, 11481-11490
17. Bhargava, B. L.; Devane, R.; Klein, M. L.; Balasubramanian, S. Nanoscale Organization in Room Temperature Ionic Liquids: A Coarse Grained Molecular Dynamics Simulation Study Soft Matter 2007, 3, 1395-1400
18. - Ionic Liquids: Insight from Molecular Dynamics Simulations Phys. Chem. Chem. Phys. 2012, 14, 5164-5177
19. Liyana-Arachchi, T. P.; Hansel, A. K.; Stevens, C.; Ehrenhauser, F. S.; Valsaraj, K. T.; Hung, F. R. Molecular Modeling of the Green Leaf Volatile Methyl Salicylate on Atmospheric Air/Water Interfaces J. Phys. Chem. A 2013, 117, 4436-4443
20. - Confined inside Multiwalled Carbon Nanotubes J. Phys. Chem. C 2010, 114, 15478-15485
21. - Confined in a Slit Nanopore J. Phys. Chem. C 2011, 115, 16544-16554
22. Llovell, F.; Marcos, R. M.; Vega, L. F. Free-Volume Theory Coupled with Soft-SAFT for Viscosity Calculations: Comparison with Molecular Simulation and Experimental Data J. Phys. Chem. B 2013, 117, 8159-8171
23. Triolo, A.; Russina, O.; Bleif, H. J.; Di Cola, E. Nanoscale Segregation in Room Temperature Ionic Liquids J. Phys. Chem. B 2007, 111, 4641-4644
24. Bowers, J.; Butts, C. P.; Martin, P. J.; Vergara-Gutierrez, M. C.; Heenan, R. K. Aggregation Behavior of Aqueous Solutions of Ionic Liquids Langmuir 2004, 20, 2191-2198
25. 2 Separations in Imidazolium-Based Room-Temperature Ionic Liquids Ind. Eng. Chem. Res. 2009, 48, 2739-2751
26. 2 Capture and Natural Gas Sweetening Energy Fuels 2010, 24, 5817-5828
27. 2 Capture with Ionic Liquids Ind. Eng. Chem. Res. 2012, 51, 8149-8177
28. 2 Capture and Comparisons to Imidazolium-Based Ionic Liquids Ind. Eng. Chem. Res. 2011, 50, 8665-8677
29. Turner, C. H.; Cooper, A.; Zhang, Z.; Shannon, M. S.; Bara, J. E. Molecular Simulation of the Thermophysical Properties of N -Functionalized Alkylimidazoles J. Phys. Chem. B 2012, 116, 6529-6535
30. Hindman, M. S.; Stanton, A. D.; Irvin, A. C.; Wallace, D. A.; Moon, J. D.; Reclusado, K. R.; Liu, H.; Belmore, K. A.; Liang, Q.; Shannon, M. S.; Turner, C. H.; Bara, J. E. Synthesis of 1,2-Dialkyl-, 1,4(5)-Dialkyl-, and 1,2,4(5)-Trialkylimidazoles Via a One-Pot Method Ind. Eng. Chem. Res. 2013, 52, 11880-11887
31. Liu, H.; Bara, J. E.; Turner, C. H. DFT Study on the Effect of Exocyclic Substituents on the Proton Affinity of 1-Methylimidazole Chem. Phys. 2013, 416, 21-25
32. Wang, Y. T.; Voth, G. A. Tail Aggregation and Domain Diffusion in Ionic Liquids J. Phys. Chem. B 2006, 110, 18601-18608
33. Smith, G. D.; Borodin, O.; Li, L.; Kim, H.; Liu, Q.; Bara, J. E.; Gin, D. L.; Nobel, R. A Comparison of Ether- and Alkyl-Derivatized Imidazolium-Based Room-Temperature Ionic Liquids: A Molecular Dynamics Simulation Study Phys. Chem. Chem. Phys. 2008, 10, 6301-6312
34. Hess, B.; Kutzner, C.; van der Spoel, D.; Lindahl, E. Gromacs 4: Algorithms for Highly Efficient, Load-Balanced, and Scalable Molecular Simulation J. Chem. Theory Comput. 2008, 4, 435-447
35. Jorgensen, W. L.; Maxwell, D. S.; TiradoRives, J. Development and Testing of the OPLS All-Atom Force Field on Conformational Energetics and Properties of Organic Liquids J. Am. Chem. Soc. 1996, 118, 11225-11236
36. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, revision A.1; Gaussian, Inc.: Wallingford, CT, 2009.
37. Becke, A. D. Density-Functional Thermochemistry. 3. The Role of Exact Exchange J. Chem. Phys. 1993, 98, 5648-5652
38. Lee, C. T.; Yang, W. T.; 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
39. Becke, A. D. A New Mixing of Hartree-Fock and Local Density-Functional Theories J. Chem. Phys. 1993, 98, 1372-1377
40. Reed, A. E.; Curtiss, L. A.; Weinhold, F. Intermolecular Interactions from a Natural Bond Orbital, Donor-Acceptor Viewpoint Chem. Rev. 1988, 88, 899-926
41. Shim, Y.; Choi, M. Y.; Kim, H. J. A Molecular Dynamics Computer Simulation Study of Room-Temperature Ionic Liquids. II. Equilibrium and Nonequilibriurn Solvation Dynamics J. Chem. Phys. 2005, 122, 044511-1-044511-12
42. Morrow, T. I.; Maginn, E. J. Molecular Dynamics Study of the Ionic Liquid 1- n -Butyl-3-Methylimidazolium Hexafluorophosphate J. Phys. Chem. B 2002, 106, 12807-12813
43. Hanke, C. G.; Price, S. L.; Lynden-Bell, R. M. Intermolecular Potentials for Simulations of Liquid Imidazolium Salts Mol. Phys. 2001, 99, 801-809
44. Hoover, W. G. Canonical Dynamics-Equilibrium Phase-Space Distributions Phys. Rev. A 1985, 31, 1695-1697
45. Parrinello, M.; Rahman, A. Crystal-Structure and Pair Potentials-a Molecular-Dynamics Study Phys. Rev. Lett. 1980, 45, 1196-1199
46. Parrinello, M.; Rahman, A. Polymorphic Transitions in Single-Crystals-a New Molecular-Dynamics Method J. Appl. Phys. 1981, 52, 7182-7190
47. Allen, M. P.; Tildesley, D. J. Computer Simulation of Liquids; Oxford University Press: Oxford, U.K., 1989.
48. Essmann, U.; Perera, L.; Berkowitz, M. L.; Darden, T.; Lee, H.; Pedersen, L. G. A Smooth Particle Mesh Ewald Method J. Chem. Phys. 1995, 103, 8577-8593
49. Potoff, J. J.; Siepmann, J. I. Vapor-Liquid Equilibria of Mixtures Containing Alkanes, Carbon Dioxide, and Nitrogen AIChE J. 2001, 47, 1676-1682
50. Martin, M. G.; Siepmann, J. I. Transferable Potentials for Phase Equilibria. 1. United-Atom Description of N-Alkanes J. Phys. Chem. B 1998, 102, 2569-2577
51. Harris, J. G.; Yung, K. H. Carbon Dioxides Liquid-Vapor Coexistence Curve and Critical Properties as Predicted by a Simple Molecular Model J. Phys. Chem. 1995, 99, 12021-12024
52. 2 in Imidazolium-Based Ionic Liquids Using NPT Monte Carlo Simulation J. Phys. Chem. B 2011, 115, 13599-13607
53. 2N]) J. Phys. Chem. B 2008, 112, 2045-2055
54. 2 Absorption J. Phys. Chem. B 2011, 115, 12487-12498
55. Perez-Blanco, M. E.; Maginn, E. J. Molecular Dynamics Simulations of Carbon Dioxide and Water at an Ionic Liquid Interface J. Phys. Chem. B 2011, 115, 10488-10499
56. Kerle, D.; Ludwig, R.; Geiger, A.; Paschek, D. Temperature Dependence of the Solubility of Carbon Dioxide in Imidazolium-Based Ionic Liquids J. Phys. Chem. B 2009, 113, 12727-12735
57. Vega, L. F.; Vilaseca, O.; Llovell, F.; Andreu, J. S. Modeling Ionic Liquids and the Solubility of Gases in Them: Recent Advances and Perspectives Fluid Phase Equilib. 2010, 294, 15-30
58. Frenkel, D.; Smit, B. Understanding Molecular Simulations: From Algorithms to Applications; Academic Press: San Diego, CA, 2002.
59. Fennell, C. J.; Gezelter, J. D. Is the Ewald Summation Still Necessary? Pairwise Alternatives to the Accepted Standard for Long-Range Electrostatics J. Chem. Phys. 2006, 124, 234104-1-234104-12
60. Wolf, D.; Keblinski, P.; Phillpot, S. R.; Eggebrecht, J. Exact Method for the Simulation of Coulombic Systems by Spherically Truncated, Pairwise R(-1) Summation J. Chem. Phys. 1999, 110, 8254-8282
61. Margulis, C. J. Computational Study of Imidazolium-Based Ionic Solvents with Alkyl Substituents of Different Lengths Mol. Phys. 2004, 102, 829-838
62. Lopes, J. N. C.; Deschamps, J.; Padua, A. A. H. Modeling Ionic Liquids Using a Systematic All-Atom Force Field J. Phys. Chem. B 2004, 108, 2038-2047
63. Canongia Lopes, J. N.; Padua, A. A. H. Molecular Force Field for Ionic Liquids III: Imidazolium, Pyridinium, and Phosphonium Cations; Chloride, Bromide, and Dicyanamide Anions J. Phys. Chem. B 2006, 110, 19586-19592
64. Lopes, J. N. C.; Padua, A. A. H.; Shimizu, K. Molecular Force Field for Ionic Liquids IV: Trialkylimidazolium and Alkoxycarbonyl-Imidazolium Cations; Alkylsulfonate and Alkylsulfate Anions J. Phys. Chem. B 2008, 112, 5039-5046
65. 2 Separations Energy Fuels 2013, 27, 3349-3357
66. Chowdhury, P.; Bikkina, C.; Gumma, S. Gas Adsorption Properties of the Chromium-Based Metal Organic Framework MIL-101 J. Phys. Chem. C 2009, 113, 6616-6621
67. 4 Separation Ind. Eng. Chem. Res. 2012, 51, 515-522
68. Paluch, A. S.; Mobley, D. L.; Maginn, E. J. Small Molecule Solvation Free Energy: Enhanced Conformational Sampling Using Expanded Ensemble Molecular Dynamics Simulation J. Chem. Theory Comput. 2011, 7, 2910-2918
69. Moore, S. G.; Wheeler, D. R. Chemical Potential Perturbation: A Method to Predict Chemical Potentials in Periodic Molecular Simulations J. Chem. Phys. 2011, 134, 114514-1-114514-11
70. Kofke, D. A.; Cummings, P. T. Quantitative Comparison and Optimization of Methods for Evaluating the Chemical Potential by Molecular Simulation Mol. Phys. 1997, 92, 973-996
71. Wierzchowski, S. J.; Monson, P. A. Calculation of Free Energies and Chemical Potentials for Gas Hydrates Using Monte Carlo Simulations J. Phys. Chem. B 2007, 111, 7274-7282
72. Neimark, A. V.; Vishnyakov, A. A Simulation Method for the Calculation of Chemical Potentials in Small, Inhomogeneous, and Dense Systems J. Chem. Phys. 2005, 122, 234108-1-234108-11
73. Cichowski, E. C.; Schmidt, T. R.; Errington, J. R. Determination of Henry's Law Constants through Transition Matrix Monte Carlo Simulation Fluid Phase Equilib. 2005, 236, 58-65