New LSER model based on solvent empirical parameters for the prediction and description of the solubility of buckminsterfullerene in various solvents

Journal of Solution Chemistry

Volumn 42, Issue 8, 2013, Pages 1620-1632

  Yousefinejad, Saeed ^a   Honarasa, Fatemeh ^b   Abbasitabar, Fatemeh ^c   Arianezhad, Zeinab ^d  

^a SHIRAZ UNIVERSITY   (Iran)

^b ISLAMIC AZAD UNIVERSITY   (Iran)

^c ISLAMIC AZAD UNIVERSITY   (Iran)

^d ISLAMIC AZAD UNIVERSITY   (Iran)

Author keywords

C60 solubility; Fullerene; LSER; QSPR; Solvent empirical parameters

Indexed keywords

EID: 84884816212     PISSN: 00959782     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10953-013-0062-2     Document Type: Article

References (44)

1. Dodziuk, H., et al.: Fullerenes. In: Dodziuk, H. (ed.) Strained Hydrocarbons, pp. 299-315. Wiley, Weinheim (2000)
2. 60 in ionic liquids. Carbon 43, 1782-1785 (2005)
3. 60. Fullerene Sci. Technol. 5, 291-310 (1997)
4. 60 fullerene. Russ. J. Gen. Chem. 73, 1227-1232 (2003)
5. Semenov, K.N., Charykov, N.A., Keskinov, V.A., Piartman, A.K., Blokhin, A.A., Kopyrin, A.A.: Solubility of light fullerenes in organic solvents. J. Chem. Eng. Data 55, 13-36 (2010)
6. Le, T., Epa, V.C., Burden, F.R., Winkler, D.A.: Quantitative structure-property relationship modeling of diverse materials properties. Chem. Rev. 112, 2889-2919 (2012)
7. Yousefinejad, S., Hemmateenejad, B., Mehdipour, A.R.: New autocorrelation QTMS-based descriptors for use in QSAM of peptides. J. Iran. Chem. Soc. 9, 569-577 (2012)
8. Yousefinejad, S., Hemmateenejad, B.: A chemometrics approach to predict the dispersibility of graphene in various liquid phases using theoretical descriptors and solvent empirical parameters. Colloids Surf. A: Physicochem. Eng. Asp. (2013). doi: 10.1016/j.colsurfa.2013.03.020
9. Todeschini, R., Consonni, V., Gramatica, P.: Chemometrics in QSAR. In: Brown, S., Walczak, B., Taulér, R. (eds.) Comprehensive Chemometrics, vol. 4, pp. 129-172. Elsevier, Oxford (2009)
10. Kamlet, M.J., Abraham, M.H., Doherty, R.M., Taft, R.W.: Solubility properties in polymers and biologicalmedia. 4. Correlations of octanol/water partition coefficients with solvatochromic parameters. J. Am. Chem. Soc. 106, 464-466 (1984)
11. Kamlet, M.J., Doherty, R.M., Carr, P.W., Mackay, D., Abraham, M.H., Taft, R.W.: Linear solvation energy relationships. 44. Parameter estimation rules that allow accurate prediction of octanol/water partition coefficients and other solubility and toxicity properties of polychlorinated biphenyls and polycyclic aromatic hydrocarbons. Environ. Sci. Technol. 22, 503-509 (1988)
12. Marcus, Y.M., Kamlet, J., Tafts, R.W.: Linear solvation energy relationships. Standard molar Gibbs free energies and enthalpies of transfer of ions from water into nonaqueous solvents. J. Phys. Chem. 92, 3613-3622 (1988)
13. Hierlemann, A., Zellers, E.T., Ricco, A.J.: Use of linear solvation energy relationships for modeling responses from polymer-coated acoustic-wave vapor sensors. Anal. Chem. 73, 3458-3466 (2001)
14. Hemmateenejad, B., Safavi, A., Dorostkar, S.: Aggregation of imidazolium based ionic liquids in binary methanol-water solvents: a linear solvation free energy relationship study. J. Mol. Liq. 160, 35-39 (2011)
15. 60 in organic solvents using optimal descriptors calculated with SMILES. Chem. Phys. Lett. 441, 119-122 (2007)
16. 60 fullerene in various solvents. Fullerenes Nanotub. Carbon Nanostruct. 16, 40-57 (2008)
17. 60 in various organic solvents by genetic algorithm-multiple linear regression. Fullerenes Nanotub. Carbon Nanostruct. 19, 585-598 (2011)
18. 60 in various solvents based on a novel approach using a least-squares support vector machine. J. Phys. Chem. B 109, 20565-20571 (2005)
19. Marcus, Y.: Solubilities of buckminsterfullerene and sulfur hexafluoride in various solvents. J. Phys. Chem. B 101, 8617-8623 (1997)
20. 60 in various solvents. J. Phys. Chem. A 104, 8081-8088 (2000)
21. Kamlet, M.J., Abboud, J.L.M., Taft, R.W.: The solvatochromic comparison method. 6. The π scale of solvent polarities. J. Am. Chem. Soc. 99, 6027-6038 (1977)
22. Katritzky, A.R., Tamm, T., Wang, Y., Sild, S., Karelson, M.: QSPR treatment of solvent scales. J. Chem. Inf. Comput. Sci. 39, 684-691 (1999)
23. Katritzky, A.R., Fara, D.C., Wang, H., Tämm, K., Karelson, M.: Quantitative measures of solvent polarity. Chem. Rev. 104, 175-198 (2004)
24. Katritzky, A.R., Fara, D.C., Kuanar, M., Hur, E., Karelson, M.: The classification of solvents by combining classical QSPR methodology with principal component analysis. J. Phys. Chem. A 109, 10323-10341 (2005)
25. Eriksson, L., Jaworska, J., Worth, A.P., Cronin, M.T.D., Mcdowell, R.M., Gramatica, P.: Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs. Environ. Health 111, 1361-1375 (2003)
26. Shao, J.U.N.: Linear model selection by cross-validation. J. Am. Stat. Assoc. 88, 486-494 (2012)
27. Consonni, V., Ballabio, D., Todeschini, R.: Evaluation of model predictive ability by external validation techniques. J. Chemometr. 24, 194-201 (2010)
28. Hawkins, D.M., Basak, S.C., Mills, D.: Assessing model fit by cross-validation. J. Chem. Inf. Comput. Sci. 43, 579-586 (2003)
29. Tetko, I.V., Livingstone, D.J., Luik, A.I.: Neural network studies. 1. Comparison of overfitting and overtraining. J. Chem. Inf. Comput. Sci. 35, 826-833 (1995)
30. Livingstone, D.J., Salt, D.W.: Judging the significance of multiple linear regression models. J. Med. Chem. 48, 661-663 (2005)
31. Rücker, C., Rücker, G., Meringer, M.: Y-randomization and its variants in QSPR/QSAR. J. Chem. Inf. Model. 47, 2345-2357 (2007)
32. Netzeva, T.I., Worth, A.P., Aldenberg, T., Benigni, R., Cronin, M.T., Gramatica, P., Jaworska, J.S., Kahn, S., Klopman, G., Marchant, C.A., Myatt, G., Nikolova-Jeliazkova, N., Patlewicz, G.Y., Perkins, R., Roberts, R., Schultz, T., Stanton, D.W., van de Sandt, J.J., Tong, W., Veith, G., Yang, C.: Current status of methods for defining the applicability domain of (quantitative) structure-activity relationships. ATLA-Altern. Lab. Anim. 33, 1-19 (2005)
33. Eriksson, L., Jaworska, J., Cronin, M., Worth, A., Gramatica, P., McDowell, R.: Methods for reliability and uncertainty assessment and for applicability evaluations of classification- and regression-based QSARs. Environ. Health Perspect. 111, 1361-1375 (2003)
34. Craney, T.A., Surles, J.G.: Model-dependent variance inflation factor cutoff values. Quality Eng. 14, 391-403 (2002)
35. Slinker, B.K., Glantz, S.A.: Multiple regression for physiological data analysis: the problem of multicollinearity. Am. J. Physiol. Regul. Integr. Comp. Physiol. 249, R1-R12 (1985)
36. Fatemi, M.H., Baher, E., Ghorbanzade'h, M.: Predictions of chromatographic retention indices of alkylphenols with support vector machines and multiple linear regression. J. Sep. Sci. 32, 4133-4142 (2009)
37. Marcus, Y.: The properties of organic liquids that are relevant to their use as solvating solvents. Chem. Soc. Rev. 22, 409-416 (1993)
38. Kamlet, M.J., Abboud, J.-L.M., Abraham, M.H., Taft, R.W.: Linear solvation energy relationships. 23. A comprehensive collection of the solvatochromic parameters, π, α, and β, and some methods for simplifying the generalized solvatochromic equation. J. Org. Chem. 48, 2877-2887 (1983)
39. Krygowski, T.M., Milcrazek, E., Wrona, P.K.: An extension of the Kamlet-Taft basicity scale of solvents. J. Chem. Soc., Perkin Trans. 2, 1563-1568 (1980)
40. Kamlet, M.J., Taft, R.W.: Linear solvation energy relationships. Part 1. Solvent polarity-polarizability effects on infrared spectra. J. Chem. Soc., Perkin Trans. 2, 337-341 (1979)
41. Abraham, M.H., Whiting, G.S., Doherty, R.M., Shuely, W.J.: Hydrogen bonding. Part 13. A new method for the characterization of GLC stationary phases-the Laffort data set. J. Chem. Soc., Perkin Trans. 2, 1451-1460 (1990)
42. Abraham, M.H., Grellier, P.L., McGill, R.A.: Determination of olive oil-gas and hexadecane-gas partition coefficients, and calculation of the corresponding olive oil-water and hexadecane-water partition coefficients. J. Chem. Soc., Perkin Trans. 2, 797-803 (1987)
43. Robinson, J.L., Roninson, W.J., Marshall, M.A., Barnes, A.D., Johnson, K.J., Salas, D.S.: Liquid-solid chromatography on amberlite XAD-2 and other styrene-divinylbenzene adsorbents. I. Development of a solvent eluotropic scale. J. Chromatogr. 189, 145-167 (1980)
44. David, J.G., Hallam, H.E.: Infrared solvent shifts and molecular interactions. Triatomic molecules, carbon disulfide, carbonyl sulfide, and sulfur dioxide. Spectrochim. Acta A 23, 593-603 (1967)