A predictive quantitative structure-property relationship for glass transition temperature of 1,3-dialkyl imidazolium ionic liquids: Part 1. The linear approach

Journal of Thermal Analysis and Calorimetry

Volumn 111, Issue 1, 2013, Pages 235-246

  Mousavisafavi, Seyed Mahmoud ^a   Mirkhani, Seyyed Alireza ^a   Gharagheizi, Farhad ^a   Akbari, Jafar ^a  

^a ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

Genetic function approximation; Glass transition temperature; Ionic liquids; Quantitative structure property relationship; Reliable model

Indexed keywords

ABSOLUTE AVERAGE DEVIATION; EXPERIMENTAL VALUES; FUNCTION APPROXIMATION; IMIDAZOLIUM IONIC LIQUIDS; LINEAR APPROACH; MOLECULAR DESCRIPTORS; PARAMETER SELECTION; QSPR MODEL; QUANTITATIVE STRUCTURE PROPERTY RELATIONSHIPS; RELIABLE MODELS; ROOT MEAN SQUARE; SQUARED CORRELATION COEFFICIENTS; STATISTICAL PARAMETERS;

ELECTROLYTES; GLASS TRANSITION;

IONIC LIQUIDS;

EID: 84872490299     PISSN: 13886150     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10973-012-2207-8     Document Type: Article

References (94)

1. Jagadeeswara Rao C, Venkata Krishnan R, Venkatesan KA, Nagarajan K, Srinivasan TG. Thermochemical properties of some bis(trifluoromethyl-sulfonyl) imide based room temperature ionic liquids. J Therm Anal Calorim. 2009;97(3):937-43.
2. Murillo-Hernández JA, López-Ramírez S, Domínguez JM, Duran-Valencia C, García-Cruz I, González-Guevara JA. Survey on ionic liquids effect based on metal anions over the thermal stability of heavy oil. J Therm Anal Calorim. 2009;95(1):173-9.
3. Andrade CKZ, Matos RAF, Oliveira VB, Duraes JA, Sales MJA. Thermal study and evaluation of new menthol-based ionic liquids as polymeric additives. J Therm Anal Calorim. 2010;99(2):539-43.
4. Stefan CS, Lemordant D, Biensan P, Siret C, Claude-Montigny B. Thermal stability and crystallization of N-alkyl-N-alkyl-pyrrolidinium imides. J Therm Anal Calorim. 2010;102(2):685-93.
5. Zhang ZH, Cui T, Zhang JL, Xiong H, Li GP, Sun LX, et al. Thermodynamic investigation of room temperature ionic liquid: the heat capacity and thermodynamic functions of BMIPF6. J Therm Anal Calorim. 2010;101(3):1143-8.
6. Amarasekara AS, Owereh OS. Thermal properties of sulfonic acid group functionalized Brönsted acidic ionic liquids. J Therm Anal Calorim. 2011;103(3):1027-30.
7. Arellano IHJ, Guarino JG, Paredes FU, Arco SD. Thermal stability and moisture uptake of 1-alkyl-3-methylimidazolium bromide. J Therm Anal Calorim. 2011;103(2):725-30.
8. Keating MY, Gao F, Ramsey JB. TGA-MS study of the decomposition of phosphorus-containing ionic liquids trihexyl(tetradecyl)phosphonium decanoate and trihexyltetradecylphosphonium bis[(trifluoromethyl)sulfonyl] amide. J Therm Anal Calorim. 2011;106(1):207-11.
9. Porcedda S, Marongiu B, Schirru M, Falconieri D, Piras A. Excess enthalpy and excess volume for binary systems of two ionic liquids + water. J Therm Anal Calorim. 2011;103(1):29-33.
10. Yue D, Jing Y, Ma J, Yao Y, Jia Y. Physicochemical properties of ionic liquid analogue containing magnesium chloride as temperature and composition dependence. J Therm Anal Calorim. 2011:1-8.
11. Ohno H. Electrolytes ionic liquids. In: Jürgen G, editor. Encyclopedia of electrochemical power sources. Amsterdam: Elsevier; 2009. p. 153-9.
12. Manuel Stephan A. Review on gel polymer electrolytes for lithium batteries. Eur Polym J. 2006;42(1):21-42. doi: 10.1016/j.eurpolymj.2005.09.017.
13. Gray FM. Solid polymer electrolytes: fundamentals and technological applications. New York: VCH; 1991.
14. Meindersma GW, Maase M, De Haan AB. Ionic liquids, Ullmann's encyclopedia of industrial chemistry. Weinham: Wiley-VCH Verlag GmbH & Co. KGaA; 2000.
15. Schalkwijk WAv, Scrosati B. Advances in lithium-ion batteries. New York: Kluwer Academic/Plenum; 2002.
16. Angell CA. Glass transition. In: Buschow KHJ, Robert WC, Merton CF, Bernard I, Edward JK, Subhash M, et al., editors. Encyclopedia of materials: science and technology. Oxford: Elsevier; 2004. p. 1-11.
17. Freemantle M. An introduction to ionic liquids. Cambridge, MA: Royal Society of Chemistry; 2010. p. 2-3.
18. Gharagheizi F. QSPR studies for solubility parameter by means of genetic algorithm-based multivariate linear regression and generalized regression neural network. QSAR Comb Sci. 2008;27(2):165-70.
19. Vatani A, Mehrpooya M, Gharagheizi F. Prediction of standard enthalpy of formation by a QSPR model. Int J Mol Sci. 2007;8(5):407-32.
20. Gharagheizi F, Sattari M, Tirandazi B. Prediction of crystal lattice energy using enthalpy of sublimation: A group contribution-based model. Ind Eng Chem Res. 2011;50(4):2482-6.
21. Gharagheizi F. QSPR analysis for intrinsic viscosity of polymer solutions by means of GA-MLR and RBFNN. Comput Mater Sci. 2007;40(1):159-67.
22. Gharagheizi F. Quantitative structure-property relationship for prediction of the lower flammability limit of pure compounds. Energy Fuels. 2008;22(5):3037-9.
23. Gharagheizi F. A QSPR model for estimation of lower flammability limit temperature of pure compounds based on molecular structure. J Hazard Mater. 2009;169(1-3):217-20.
24. Gharagheizi F, Eslamimanesh A, Mohammadi AH, Richon D. QSPR approach for determination of parachor of non-electrolyte organic compounds. Chem Eng Sci. 2011;66(13):2959-67.
25. Gharagheizi F, Gohar MRS, Vayeghan MG. A quantitative structure-property relationship for determination of enthalpy of fusion of pure compounds. J Therm Anal Calorim. 2011:1-6.
26. Gharagheizi F, Babaie O, Mazdeyasna S. Prediction of vaporization enthalpy of pure compounds using a group contribution-based method. Ind Eng Chem Res. 2011;50(10):6503-7.
27. Gharagheizi F, Tirandazi B, Barzin R. Estimation of aniline point temperature of pure hydrocarbons: a quantitative structure-property relationship approach. Ind Eng Chem Res. 2009;48(3):1678-82.
28. Bonhôte P, Dias A-P, Papageorgiou N, Kalyanasundaram K, Grätzel M. Hydrophobic, highly conductive ambient-temperature molten salts. Inorg Chem. 1996;35(5):1168-78. doi: 10.1021/ic951325x.
29. Branco LC, Rosa JN, Moura Ramos JJ, Afonso CAM. Preparation and characterization of new room temperature ionic liquids. Chem A Eur J. 2002;8(16):3671-7. doi: 10.1002/1521-3765(20020816)8:16<3671:AID- chem3671>3.0.co;2-9.
30. Cha EH, Lim SA, Park JH, Kim DW, Macfarlane DR. Ionic conductivity studies of gel polyelectrolyte based on ionic liquid. J Power Sources. 2008;178(2):779-82. doi: 10.1016/j.jpowsour.2007.10.033.
31. Chun S, Dzyuba SV, Bartsch RA. Influence of structural variation in room-temperature ionic liquids on the selectivity and efficiency of competitive alkali metal Salt extraction by a crown ether. Anal Chem. 2001;73(15):3737-41. doi: 10.1021/ac010061v.
32. Crosthwaite JM, Muldoon MJ, Dixon JK, Anderson JL, Brennecke JF. Phase transition and decomposition temperatures, heat capacities and viscosities of pyridinium ionic liquids. J Chem Thermodyn. 2005;37(6):559-68. doi: 10.1016/j.jct.2005.03.013.
33. D. Holbrey J, R. Seddon K. The phase behaviour of 1-alkyl-3- methylimidazolium tetrafluoroborates; ionic liquids and ionic liquid crystals. J Chem Soc Dalton Trans. 1999(13):2133-40.
34. Domańska U, Bogel-Łukasik E, Bogel-Łukasik R. 1-Octanol/water partition coefficients of 1alkyl-3-methylimidazolium chloride. Chem A Eur J. 2003;9(13):3033-41. doi: 10.1002/chem.200204516.
35. Dzyuba SV, Bartsch RA. Influence of structural variations in 1-alkyl(aralkyl)-3-methylimidazolium hexafluorophosphates and bis(trifluoromethylsulfonyl)imides on physical properties of the ionic liquids. ChemPhysChem. 2002;3(2):161-6. doi: 10.1002/1439-7641(20020215)3:2<161:aid- cphc161>3.0.co;2-3.
36. Dzyuba SV, Bartsch RA. Expanding the polarity range of ionic liquids. Tetrahedron Lett. 2002;43(26):4657-9. doi: 10.1016/s0040-4039(02)00858-4.
37. Fredlake CP, Crosthwaite JM, Hert DG, Aki SNVK, Brennecke JF. Thermophysical properties of imidazolium-based ionic liquids. J Chem Eng Data. 2004;49(4):954-64. doi: 10.1021/je034261a.
38. Fukumoto K, Yoshizawa M, Ohno H. Room temperature ionic liquids from 20 natural amino acids. J Am Chem Soc. 2005;127(8):2398-9. doi: 10.1021/ja043451i.
39. Holbrey JD, Turner MB, Reichert WM, Rogers RD. New ionic liquids containing an appended hydroxyl functionality from the atom-efficient, one-pot reaction of 1-methylimidazole and acid with propylene oxide. Green Chem. 2003;5(6):731. doi: 10.1039/b311717k.
40. Huddleston JG, Visser AE, Reichert WM, Willauer HD, Broker GA, Rogers RD. Characterization and comparison of hydrophilic and hydrophobic room temperature ionic liquids incorporating the imidazolium cation. Green Chem. 2001;3(4):156-64. doi: 10.1039/b103275p.
41. J. Earle M, B. McCormac P, R. Seddon K. Regioselective alkylation in ionic liquids. Chem Commun. 1998(20):2245-6.
42. Jodry JJ, Mikami K. New chiral imidazolium ionic liquids: 3D-network of hydrogen bonding. Tetrahedron Lett. 2004;45(23):4429-31. doi: 10.1016/j.tetlet.2004.04.063.
43. Kulkarni PS, Branco LC, Crespo JG, Nunes MC, Raymundo A, Afonso CAM. Comparison of physicochemical properties of new ionic liquids based on imidazolium, quaternary ammonium, and guanidinium cations. Chem A Eur J. 2007;13(30):8478-88. doi: 10.1002/chem.200700965.
44. MacFarlane DR, Golding J, Forsyth S, Forsyth M, Deacon GB. Low viscosity ionic liquids based on organic salts of the dicyanamide anion. Chem Commun. 2001;16:1430-1.
45. Matsumoto K, Hagiwara R. A new room temperature ionic liquid of oxyfluorometallate anion: 1-ethyl-3-methylimidazolium oxypentafluorotungstate (EMImWOF5). J Fluor Chem. 2005;126(7):1095-100. doi: 10.1016/j.jfluchem.2005.03. 018.
46. Matsumoto K, Hagiwara R, Ito Y. Room temperature molten fluorometallates: 1-ethyl-3-methylimidazolium hexafluoroniobate(V) and hexafluorotantalate(V). J Fluor Chem. 2002;115(2):133-5. doi: 10.1016/s0022-1139(02)00037-4.
47. McEwen AB, Ngo HL, LeCompte K, Goldman JL. Electrochemical properties of imidazolium salt electrolytes for electrochemical capacitor applications. J Electrochem Soc. 1999;146(5):1687-95. doi: 10.1149/1.1391827.
48. Moura Ramos J, Afonso C, Branco L. Glass transition relaxation and fragility in two room temperature ionic liquids. J Therm Anal Calorim. 2003;71(2):659-66. doi: 10.1023/a:1022884716750.
49. Mu ZG, Zhou F, Zhang SX, Liang YM, Liu WM. Preparation and characterization of new phosphonyl-substituted imidazolium ionic liquids. Helvetica Chimica Acta. 2004;87(10):2549-55. doi: 10.1002/hlca.200490227.
50. Ngo HL, LeCompte K, Hargens L, McEwen AB. Thermal properties of imidazolium ionic liquids. Thermochim Acta. 2000;357-358:97-102. doi: 10.1016/s0040-6031(00)00373-7.
51. Nishida T. Physical and electrochemical properties of 1-alkyl-3-methylimidazolium tetrafluoroborate for electrolyte. J Fluor Chem. 2003;120(2):135-41. doi: 10.1016/s0022-1139(02)00322-6.
52. Noda A, Hayamizu K, Watanabe M. Pulsed-gradient spin-echo 1H and 19F NMR ionic diffusion coefficient, viscosity, and ionic conductivity of non-chloroaluminate room-temperature ionic liquids. J Phys Chem B. 2001;105(20):4603-10. doi: 10.1021/jp004132q.
53. Ogihara W, Washiro S, Nakajima H, Ohno H. Effect of cation structure on the electrochemical and thermal properties of ion conductive polymers obtained from polymerizable ionic liquids. Electrochim Acta. 2006;51(13):2614-9. doi: 10.1016/j.electacta.2005.07.043.
54. Ohno H. Ion conductive characteristics of ionic liquids prepared by neutralization of alkylimidazoles. Solid State Ionics. 2002;154-155:303-9. doi: 10.1016/s0167-2738(02)00526-x.
55. Omotowa BA, Shreeve JnM. Triazine-based polyfluorinated triquaternary liquid salts: synthesis, characterization, and application as solvents in rhodium(I)-catalyzed hydroformylation of 1-octene. Organometallics. 2004;23(4):783-91. doi: 10.1021/om0342311.
56. Ouadi A, Gadenne B, Hesemann P, Moreau JJE, Billard I, Gaillard C, et al. Task-specific ionic liquids bearing 2-hydroxybenzylamine units: synthesis and americium-extraction studies. Chem A Eur J. 2006;12(11):3074-81. doi: 10.1002/chem.200500741.
57. Park HS, Choi YS, Jung YM, Hong WH. Intermolecular interaction-induced hierarchical transformation in 1D nanohybrids: analysis of conformational changes by 2D correlation spectroscopy. J Am Chem Soc. 2007;130(3):845-52. doi: 10.1021/ja073074k.
58. Pringle JM, Golding J, Baranyai K, Forsyth CM, Deacon GB, Scott JL, et al. The effect of anion fluorination in ionic liquids-physical properties of a range of bis(methanesulfonyl)amide salts. New J Chem. 2003;27(10):1504-10.
59. Qi M, Wu G, Li Q, Luo Y. γ-Radiation effect on ionic liquid [bmim][BF4]. Radiat Phys chem. 2008;77(7):877-83. doi: 10.1016/j.radphyschem. 2007.12.007.
60. Sato T. Electrochemical properties of novel ionic liquids for electric double layer capacitor applications. Electrochimica Acta. 2004;49(21):3603-11. doi: 10.1016/j.electacta.2004.03.030.
61. Song Y, Liu L, Zhu X, Wang X, Jia H, Xiao X, et al. Physicochemical properties of ionic liquids based on imidazolium/pyrrolidinium cations and maleate/phthalate anions. Solid State Ionics. 2008;179(13-14):516-21. doi: 10.1016/j.ssi.2008.03.035.
62. Strechan AA, Paulechka YU, Blokhin AV, Kabo GJ. Low-temperature heat capacity of hydrophilic ionic liquids [BMIM][CF3COO] and [BMIM][CH3COO] and a correlation scheme for estimation of heat capacity of ionic liquids. J Chem Thermodyn. 2008;40(4):632-9. doi: 10.1016/j.jct.2007.11.004.
63. Suarez PAZ, Dullius JEL, Einloft S, De Souza RF, Dupont J. The use of new ionic liquids in two-phase catalytic hydrogenation reaction by rhodium complexes. Polyhedron. 1996;15(7):1217-9. doi: 10.1016/0277-5387(95)00365-7.
64. Suarez PAZ, Einloft S, Dullius JEL, De Souza RF, Dupont J. Synthesis and physical-chemical properties of ionic liquids based on 1-n-butyl-3- methylimidazolium cation. Journal de Chimie Physique et de Physico-Chimie Biologique. 1998;95(7):1626-39.
65. Tosoni M, Laschat S, Baro A. Synthesis of novel chiral ionic liquids and their phase behavior in mixtures with smectic and nematic liquid crystals. Helvetica Chimica Acta. 2004;87(11):2742-9. doi: 10.1002/hlca.200490247.
66. Valkenburg M, Vaughn R, Williams M, Wilkes J. Thermochemistry of ionic liquid heat-transfer fluids. Thermochim Acta. 2005;425(1-2):181-8. doi: 10.1016/j.tca.2004.11.013.
67. Visser Ann E, Reichert WM, Swatloski Richard P, Willauer Heather D, Huddleston Jonathan G, Rogers Robin D. Characterization of hydrophilic and hydrophobic ionic liquids: alternatives to volatile organic compounds for liquid-liquid separations. Ionic liquids. ACS symposium Series 818. Washington DC: American Chemical Society; 2002. p. 289-308.
68. Xu W, Wang L-M, Nieman RA, Angell CA. Ionic liquids of chelated orthoborates as model ionic glassformers. J Phys Chem B. 2003;107(42):11749-56. doi: 10.1021/jp034548e.
69. Yagupolskii YL, Sokolenko TM, Petko KI, Yagupolskii LM. Novel ionic liquids - Imidazolium salts with a difluoromethylene fragment directly bonded to the nitrogen atom. J Fluor Chem. 2005;126(4):669-72.
70. Ye C, Shreeve JNM. Syntheses of very dense halogenated liquids. J Org Chem. 2004;69(19):6511-3. doi: 10.1021/jo0490649.
71. Yeon S, Kim K, Choi S, Lee H, Kim H. Physical and electrochemical properties of 1-(2-hydroxyethyl)-3-methyl imidazolium and N-(2-hydroxyethyl)-N- methyl morpholinium ionic liquids. Electrochimica Acta. 2005;50(27):5399-407. doi: 10.1016/j.electacta.2005.03.020.
72. Yoshida Y, Muroi K, Otsuka A, Saito G, Takahashi M, Yoko T. 1-Ethyl-3-methylimidazolium based ionic liquids containing cyano groups: synthesis, characterization, and crystal structure. Inorg Chem. 2004;43(4):1458-62. doi: 10.1021/ic035045q.
73. Zhou Z-B, Matsumoto H, Tatsumi K. Low-melting, low-viscous, hydrophobic ionic liquids: 1-alkyl(alkyl ether)-3-methylimidazolium perfluoroalkyltrifluoroborate. Chem A Eur J. 2004;10(24):6581-91. doi: 10.1002/chem.200400533.
74. Zhou Z-B, Matsumoto H, Tatsumi K. Structure and properties of new ionic liquids based on alkyl- and alkenyltrifluoroborates. ChemPhysChem. 2005;6(7):1324-32. doi: 10.1002/cphc.200500094.
75. Rogers D, Hopfinger AJ. Application of genetic function approximation to quantitative structure-activity relationships and quantitative structure-property relationships. J Chem Inf Comput Sci. 1994;34(4):854-66.
76. Friedman JH. Multivariate adaptive regression splines. Ann Stat. 1991;19(1):1-67. doi: 10.1214/aos/1176347963.
77. Holland JH. Adaptation in natural and artificial systems: an introductory analysis with applications to biology, control, and artificial intelligence. 1st ed. Cambridge, MA: MIT Press; 1992.
78. Ahmed SSSJ, Ahameethunisa A, Santosh W. QSAR and pharmacophore modeling of 4-arylthieno [3, 2-d] pyrimidine derivatives against adenosine receptor of Parkinson's disease. J Theor Comput Chem. 2010;9(6):975-91.
79. Chhabria MT, Jani M, Parmar K, Singh M. QSAR study of a series of 2,3-dihydroimidazo[1,2-c]pyrimidines as antibacterial agents. Medicinal Chemistry Research. 2010:1-8.
80. Chhabria MT, Suhagia BN, Mandhare AB, Brahmkshatriya PS. QSAR study of a series of cholesteryl ester transfer protein inhibitors. Collect Czech Chem Commun. 2011;76(7):803-13.
81. Khaled KF. Modeling corrosion inhibition of iron in acid medium by genetic function approximation method: a QSAR model. Corros Sci. 2011;53(11):3457-65.
82. Ojha PK, Roy K. Chemometric modelling of antimalarial activity of aryltriazolylhydroxamates. Mol Simul. 2010;36(12):939-52.
83. Reyes OJ, Patel SJ, Mannan MS. Quantitative structure property relationship studies for predicting dust explosibility characteristics (Kst, Pmax) of organic chemical dusts. Ind Eng Chem Res. 2011;50(4):2373-9.
84. Sivakumar PM, Iyer G, Doble M. QSAR studies on substituted 3- or 4-phenyl-1,8-naphthyridine derivatives as antimicrobial agents. Med Chem Res. 2011:1-8.
85. Gharagheizi F. An accurate model for prediction of autoignition temperature of pure compounds. J Hazard Mater. 2011;189(1-2):211-21.
86. Liu H, Yao X, Zhang R, Liu M, Hu Z, Fan B. Accurate quantitative structure-property relationship model to predict the solubility of C60 in various solvents based on a novel approach using a least-squares support vector machine. J Phys Chem B. 2005;109(43):20565-71.
87. Burden FR. Molecular identification number for substructure searches. J Chem Inf Comput Sci. 1989;29(3):225-7. doi: 10.1021/ci00063a011.
88. Pearlman RS, Smith KM. Metric validation and the receptor-relevant subspace concept. J Chem Inf Comput Sci. 1999;39(1):28-35. doi: 10.1021/ci980137x.
89. Gao H. Application of BCUT metrics and genetic algorithm in binary QSAR analysis. J Chem Inf Comput Sci. 2001;41(2):402-7. doi: 10.1021/ci000306p.
90. Stanton DT. Evaluation and use of BCUT descriptors in QSAR and QSPR studies. J Chem Inf Comput Sci. 1998;39(1):11-20. doi: 10.1021/ci980102x.
91. Todeschini R, Consonni V. Molecular descriptors for chemoinformatics. 2nd ed. Weinheim: Wiley-VCH; 2009.
92. Krzanowski WJ. Principles of multivariate analysis: a user's perspective. Oxford: Oxford University Press; 2000.
93. Todeschini R, Consonni V, Mauri A, Pavan M. Detecting "bad" regression models: multicriteria fitness functions in regression analysis. Analytica Chimica Acta. 2004;515(1):199-208. doi: 10.1016/j.aca.2003.12.010.
94. Chiou J. Hybrid method of evolutionary algorithms for static and dynamic optimization problems with application to a fed-batch fermentation process. Comput Chem Eng. 1999;23(9):1277-91. doi: 10.1016/s0098-1354(99)00290-2.