Nanostructural Reorganization Manifests in Sui-Generis Density Trend of Imidazolium Acetate/Water Binary Mixtures

Journal of Physical Chemistry B

Volumn 119, Issue 34, 2015, Pages 10911-10920

  Ghoshdastidar, Debostuti ^a   Senapati, Sanjib ^a  

^a INDIAN INSTITUTE OF TECHNOLOGY MADRAS   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALINITY; IONIC LIQUIDS; MIXTURES; MOLECULAR DYNAMICS; POSITIVE IONS; THERMODYNAMIC PROPERTIES;

BIO-CHEMICAL APPLICATIONS; BIOCHEMICAL RESEARCH; IMIDAZOLIUM CATION; IONIC LIQUID (ILS); MODERATE CONCENTRATION; MOLECULAR DYNAMICS SIMULATIONS; SPATIAL CORRELATIONS; WATER CONCENTRATIONS;

BINARY MIXTURES;

ACETIC ACID DERIVATIVE; HYGROSCOPIC AGENT; IMIDAZOLE DERIVATIVE; NANOMATERIAL; WATER;

CHEMISTRY; MOLECULAR DYNAMICS;

ACETATES; HYGROSCOPIC AGENTS; IMIDAZOLES; MOLECULAR DYNAMICS SIMULATION; NANOSTRUCTURES; WATER;

EID: 84940480327     PISSN: 15206106     EISSN: 15205207     Source Type: Journal    
DOI: 10.1021/acs.jpcb.5b00433     Document Type: Article

References (69)

1. Petkovic, M.; Seddon, K. R.; Rebelo, L. P. N.; Pereira, C. S. Ionic Liquids: A Pathway to Environmental Acceptability Chem. Soc. Rev. 2011, 40, 1383-1403
2. Cevascoa, G.; Chiappe, C. Are Ionic Liquids a Proper Solution to Current Environmental Challenges? Green Chem. 2014, 16, 2375-2385
3. Hu, Y.-F.; Liu, Z.-C.; Xu, C.-M.; Zhang, X.-M. The Molecular Characteristics Dominating the Solubility of Gases in Ionic Liquids Chem. Soc. Rev. 2011, 40, 3802-3823
4. Lopes, J. N. C.; Gomes, M. F. C.; Pádua, M. F. C. Nonpolar, Polar, and Associating Solutes in Ionic Liquids J. Phys. Chem. B 2006, 110, 16816-16818
5. Pádua, A. A. H.; Gomes, M. F. C.; Lopes, J. N. C. Molecular Solutes in Ionic Liquids: A Structural Perspective Acc. Chem. Res. 2007, 40, 1087-1096
6. Rogers, R. D.; Seddon, K. R. Ionic Liquids-Solvents of the Future? Science 2003, 302, 792-793
7. Giernoth, R. Task-Specific Ionic Liquids Angew. Chem., Int. Ed. 2010, 49, 2834-2839
8. Greaves, T. L.; Drummond, C. J. Ionic Liquids as Amphiphile Self-assembly Media Chem. Soc. Rev. 2008, 37, 1709-1726
9. Hallett, J. P.; Welton, T. Room-Temperature Ionic Liquids: Solvents for Synthesis and Catalysis Chem. Rev. 2011, 111, 3508-3576
10. van Rantwijk, F.; Sheldon, R. A. Biocatalysis in Ionic Liquids Chem. Rev. 2007, 107, 2757-2785
11. Garcia, H.; Ferreira, R.; Petkovic, M.; Ferguson, J. L.; Leitao, M. C.; Gunaratne, H. Q. N.; Seddon, K. R.; Rebelo, L. P. N.; Pereira, C. S. Dissolution of Cork Biopolymers in Biocompatible Ionic Liquids Green Chem. 2010, 12, 367-369
12. Araújo, J. M. M.; Pereiro, A. B.; Lopes, J. N. C.; Rebelo, L. P. N.; Marrucho, I. M. Hydrogen-Bonding and the Dissolution Mechanism of Uracil in an Acetate Ionic Liquid: New insights from NMR Spectroscopy and Quantum Chemical Calculations J. Phys. Chem. B 2013, 117, 4109-4120
13. Zhao, H.; Baker, G. A.; Song, Z.; Olubajo, O.; Crittle, T.; Peters, D. Designing Enzyme-Compatible Ionic Liquids That Can Dissolve Carbohydrates Green Chem. 2008, 10, 696-705
14. Vijayaraghavan, R.; Izgorodin, A.; Ganesh, V.; Surianarayanan, M.; MacFarlane, D. R. Long-term Structural and Chemical Stability of DNA in Hydrated Ionic Liquids Angew. Chem., Int. Ed. 2010, 49, 1631-1633
15. Zhao, H. Methods for Stabilizing and Activating Enzymes in Ionic Liquids -A Review J. Chem. Technol. Biotechnol. 2010, 85, 891-907
16. Armand, M.; Endres, F.; Macfarlane, D. R.; Ohno, H.; Scrosati, B. Ionic-Liquid Materials for the Electrochemical Challenges of the Future Nat. Mater. 2009, 8, 621-629
17. Swatloski, R. P.; Spear, S. K.; Holbrey, J. D.; Rogers, R. D. Dissolution of Cellulose with Ionic Liquids J. Am. Chem. Soc. 2002, 124, 4974-4975
18. Seddon, K. R.; Stark, A.; Torres, M.-J. Influence of Chloride, Water, and Organic Solvents on the Physical Properties of Ionic Liquids Pure Appl. Chem. 2000, 72, 2275-2287
19. Jacquemin, J.; Husson, J. P.; Padua, A. A. H.; Majer, V. Density and Viscosity of Several Pure and Water-Saturated Ionic Liquids Green Chem. 2006, 8, 172-180
20. Rodriguez, H.; Brennecke, J. F. Temperature and Composition Dependence of the Density and Viscosity of Binary Mixtures of Water + Ionic Liquid J. Chem. Eng. Data 2006, 51, 2145-2155
21. Liu, W.; Cheng, L.; Zhang, Y.; Wang, H.; Yu, M. The Physical Properties of Aqueous Solution of Room-Temperature Ionic Liquids Based on Imidazolium: Database and Evaluation J. Mol. Liq. 2008, 140, 68-72
22. Tariq, M.; Freire, M. G.; Saramago, B.; Coutinho, J. A. P.; Lopes, J. N. C.; Rebelo, L. P. N. Surface Tension of Ionic Liquids and Ionic Liquid Solutions Chem. Soc. Rev. 2012, 41, 829-868
23. Freire, M. G.; Carvalho, P. J.; Fernandes, A. M.; Marrucho, I. M.; Queimada, A. J.; Coutinho, J. A. P. Surface Tensions of Imidazolium Based Ionic Liquids: Anion, Cation, Temperature and Water Effect J. Colloid Interface Sci. 2007, 314, 621-630
24. Widegren, J. A.; Saurer, E. M.; Marsh, K. N.; Magee, J. W. Electrolytic Conductivity of Four Imidazolium-Based Room-Temperature Ionic Liquids and the Effect of a Water Impurity J. Chem. Thermodyn. 2005, 37, 569-575
25. Kohno, Y.; Ohno, H. Temperature-Responsive Ionic Liquid/Water interfaces: Relation Between Hydrophilicity of Ions and Dynamic Phase Change Phys. Chem. Chem. Phys. 2012, 14, 5063-5070
26. Bahadur, I.; Letcher, T. M.; Singh, S.; Redhi, G. G.; Venkatesu, P.; Ramjugernath, D. Excess Molar Volumes of Binary Mixtures (an Ionic Liquid + Water): A Review J. Chem. Thermodyn. 2015, 82, 34-46
27. García-Miaja, G.; Troncoso, J.; Romaní, L. Excess Enthalpy, Density, and Heat Capacity for Binary Systems of Alkylimidazolium-Based Ionic Liquids + Water J. Chem. Thermodyn. 2009, 41, 161-166
28. Stevanovic, S.; Podgoršek, A.; Pádua, A. A. H.; Gomes, M. F. C. Effect of Water on the Carbon Dioxide Absorption by 1-Alkyl-3-Methylimidazolium Acetate Ionic Liquids J. Phys. Chem. B 2012, 116, 14416-14425
29. Quijada-Maldonado, E.; van der Boogaart, S.; Lijbers, J. H.; Meindersma, G. W.; de Haan, A. B. Experimental Densities, Dynamic Viscosities and Surface Tensions of the Ionic Liquids Series 1-Ethyl-3-Methylimidazolium Acetate and Dicyanamide and their Binary and Ternary Mixtures with Water and Ethanol at T = (298.15 to 343.15 K) J. Chem. Thermodyn. 2012, 51, 51-58
30. Hall, C. A.; Le, K. A.; Rudaz, C.; Radhi, A.; Lovell, C. S.; Damion, R. A.; Budtova, T.; Ries, M. E. Macroscopic and Microscopic Study of 1-Ethyl-3-Methyl-Imidazolium Acetate-Water Mixtures J. Phys. Chem. B 2012, 116, 12810-12818
31. Guan, W.; Ma, X.-X.; Li, L.; Tong, J.; Fang, D.-W.; Yang, J.-Z. Ionic Parachor and Its Application in Acetic Acid Ionic Liquid Homologue 1-Alkyl-3-Methylimidazolium Acetate {[Cnmim][Oac](N = 2,3,4,5,6)} J. Phys. Chem. B 2011, 115, 12915-12920
32. 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
33. 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
34. Russina, O.; Triolo, A.; Gontrani, L.; Caminiti, R. Mesoscopic Structural Heterogeneities in Room-Temperature Ionic Liquids J. Phys. Chem. Lett. 2012, 3, 27-33
35. Shimizu, K.; Gomes, M. F. C.; Pádua, A. A. H.; Rebelo, L. P. N.; Lopes, J. N. C. Three Commentaries on the Nano-Segregated Structure of Ionic Liquids J. Mol. Struct.: THEOCHEM 2010, 946, 70-76
36. Zheng, W.; Mohammed, A.; Hines, L. G., Jr. ; Xiao, D.; Martinez, O. J.; Bartsch, R. A.; Simon, S. L.; Russina, O.; Triolo, A.; Quitevis, E. L. Effect of Cation Symmetry on the Morphology and Physicochemical Properties of Imidazolium Ionic Liquids J. Phys. Chem. B 2011, 115, 6572-6584
37. 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
38. Lopes, J. N. C.; Padua, A. A. H. Nanostructural Organization in Ionic Liquids J. Phys. Chem. B 2006, 110, 3330-3335
39. Wang, Y.; Voth, G. A. Tail Aggregation and Domain Diffusion in Ionic Liquids J. Phys. Chem. B 2006, 110, 18601-18606
40. Jiang, W.; Wang, Y.; Voth, G. A. Molecular Dynamics Simulation of Nanostructural Organization in Ionic Liquid/Water Mixtures J. Phys. Chem. B 2007, 111, 4812-4818
41. Feng, S.; Voth, G. A. Molecular Dynamics Simulations of Imidazolium-Based Ionic Liquid/Water Mixtures: Alkyl Side Chain Length and Anion Effects Fluid Phase Equilib. 2010, 294, 148-156
42. Bhargava, B. L.; Klein, M. L. Initial Stages of Aggregation in Aqueous Solutions of Ionic Liquids: Molecular Dynamics Studies J. Phys. Chem. B 2009, 113, 9499-9505
43. Bernardes, C. E. S.; da Piedade, M. E. M.; Lopes, J. N. C. The Structure of Aqueous Solutions of a Hydrophilic Ionic Liquid: The Full Concentration Range of 1-Ethyl-3-Methylimidazolium Ethylsulfate and Water J. Phys. Chem. B 2011, 115, 2067-2074
44. Sturlaugson, A. L.; Fruchey, K. S.; Fayer, M. D. Orientational Dynamics of Room Temperature Ionic Liquid/Water Mixtures: Water-induced Structure J. Phys. Chem. B 2012, 116, 1777-1787
45. Ramya, K. R.; Kumar, P.; Kumar, A.; Venkatnathan, A. Interplay of Phase Separation, Tail Aggregation, and Micelle formation in the Nanostructured Organization of Hydrated Imidazolium Ionic Liquid J. Phys. Chem. B 2014, 118, 8839-8847
46. Tokuda, H.; Hayamizu, K.; Ishii, K.; Hasan Susan, A. B.; Md; Watanabe, M. Physicochemical Properties and Structures of Room Temperature Ionic Liquids. 2. Variation of Alkyl Chain Length in Imidazolium Cation J. Phys. Chem. B 2005, 109, 6103-6110
47. Wu, Y.; Ma, X.; Li, Y.; Guan, W.; Tong, J.; Hu, N. Theoretical and Experimental Determination of the Number of Water Molecules Breaking the Structure of a Glycine-Based Ionic Liquid R. Soc. Chem. Adv. 2014, 4, 10531-10541
48. Frisch, M. J.; et al., Gaussian 09, revision B.01; Gaussian, Inc.: Wallingford, CT, 2010.
49. 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
50. Liu, Z.; Huang, S.; Wang, W. A Refined force Field for Molecular Simulation of Imidazolium-Based Ionic Liquids J. Phys. Chem. B 2004, 108, 12978-12989
51. Chandran, A.; Prakash, K.; Senapati, S. Structure and Dynamics of Acetate Anion-Based Ionic Liquids from Molecular Dynamics Study Chem. Phys. 2010, 374, 46-54
52. Case, D. A.; et al., AMBER 12; University of California, San Francisco: San Francisco, CA, 2012.
53. Rilo, E.; Pico, J.; García-Garabal, S.; Varela, L. M.; Cabeza, O. Density and Surface Tension in Binary Mixtures of Cnmim-BF4 Ionic Liquids with Water and Ethanol Fluid Phase Equilib. 2009, 285, 83-89
54. Wang, J.; Jiang, H.-C.; Liu, Y.-M.; Hu, Y.-Q. Density and Surface Tension of Pure 1-Ethyl-3-Methylimidazolium l -Lactate Ionic Liquid and its Binary Mixtures with Water J. Chem. Thermodyn. 2011, 43, 800-804
55. González, E. J.; Domínguez, A.; Macedo, E. A. Physical and Excess Properties of Eight Binary Mixtures Containing Water and Ionic Liquids J. Chem. Eng. Data 2012, 57, 2165-2176
56. Gomez, E.; Gonzalez, B.; Calvar, N.; Tojo, E.; Dominguez, A. Physical Properties of Pure 1-Ethyl-3-Methylimidazolium Ethylsulfate and Its Binary Mixtures with Ethanol and Water at Several Temperatures J. Chem. Eng. Data 2006, 51, 2096-2102
57. Alvarez, V. H.; Mattedi, S.; Martin-Pastor, M.; Aznar, M.; Iglesias, M. Thermophysical Properties of Binary Mixtures of {Ionic Liquid 2-Hydroxy Ethylammonium Acetate + (Water, Methanol, Or Ethanol)} J. Chem. Thermodyn. 2011, 43, 997-1010
58. Vercher, E.; Miguel, P. J.; Llopis, F. J.; Orchillés, A. V.; Martínez-Andreu, A. Volumetric and Acoustic Properties of Aqueous Solutions of Trifluoromethanesulfonate-Based Ionic Liquids at Several Temperatures J. Chem. Eng. Data 2012, 57, 1953-1963
59. Fredlake, C. P.; Crosthwaite, J. M.; Hert, D. G.; Aki, S. N. V. K.; Brennecke, J. F. Thermophysical Properties of Imidazolium-Based Ionic Liquids J. Chem. Eng. Data 2004, 49, 954-964
60. Yang, Q.; Zhang, H.; Su, B.; Yang, Y.; Ren, Q.; Xing, H. Volumetric Properties of Binary Mixtures of 1-Butyl-3-Methylimidazolium Chloride + Water or Hydrophilic Solvents at Different Temperatures J. Chem. Eng. Data 2010, 55, 1750-1754
61. Luzar, A.; Chandler, D. Hydrogen-Bond Kinetics in Liquid Water Nature 1996, 379, 55-57
62. Rahman, H. M. A.; Hefter, G.; Buchner, R. Hydration of Formate and Acetate Ions by Dielectric Relaxation Spectroscopy J. Phys. Chem. B 2012, 116, 314-323
63. Bowron, D. T.; D'Agostino, C.; Gladden, L. F.; Hardacre, C.; Holbrey, J. D.; Lagunas, M. C.; Mcgregor, J.; Mantle, M. D.; Mullan, C. L.; Youngs, T. G. A. Structure and Dynamics of 1-Ethyl-3-Methylimidazolium Acetate via Molecular Dynamics and Neutron Diffraction J. Phys. Chem. B 2010, 114, 7760-7768
64. Hunt, P. A.; Ashworth, C. R.; Matthews, R. P. Hydrogen Bonding in Ionic Liquids Chem. Soc. Rev. 2015, 44, 1257-1288
65. Shi, W.; Damodaran, K.; Nulwala, H. B.; Luebke, D. R. Theoretical and Experimental Studies of Water interaction in Acetate Based Ionic Liquids Phys. Chem. Chem. Phys. 2012, 14, 15897-15908
66. Zhang, Y.; Maginn, E. J. A Simple AIMD Approach to Derive Atomic Charges for Condensed Phase Simulation of Ionic Liquids J. Phys. Chem. B 2012, 116, 10036-10048
67. Mondal, A.; Balasubramanian, S. Quantitative Prediction of Physical Properties of Imidazolium Based Room Temperature Ionic Liquids through Determination of Condensed Phase Site Charges: A Refined force Field J. Phys. Chem. B 2014, 118, 3409-3422
68. Gontrani, L.; Bodo, E.; Triolo, A.; Leonelli, F.; d'Angelo, P.; Migliorati, V.; Caminiti, R. The Interpretation of Diffraction Patterns of Two Prototypical Protic Ionic Liquids: A Challenging Task for Classical Molecular Dynamics Simulations J. Phys. Chem. B 2012, 116, 13024-13032
69. van der Spoel, D.; van Maaren, P. J.; Berendsen, H. J. C. A Systematic Study of Water Models for Molecular Simulation: Derivation of Water Models Optimized for Use with a Reaction Field J. Chem. Phys. 1998, 108, 10220-10230