Development of semi-empirical electrotopological index using the atomic charge in QSPR/QSRR models for alcohols

Journal of Chemometrics

Volumn 24, Issue 3-4, 2010, Pages 149-157

  Souza, Érica Silva ^a   Kuhnen, Carlos Alberto ^a   Junkes, Berenice da Silva ^b   Yunes, Rosendo Augusto ^a   Heinzen, Vilma Edite Fonseca ^a  

^a FEDERAL UNIVERSITY OF SANTA CATARINA   (Brazil)

^b Science and Technology of Santa Catarina   (Brazil)

Author keywords

Alcohols; Gas chromatographic retention indices; QSPR; Semi empirical electrotopological index

Indexed keywords

GAS CHROMATOGRAPHY; HYDROCARBONS;

ALIPHATIC ALCOHOL; ATOMIC CHARGE; CHROMATOGRAPHIC RETENTION; GAS CHROMATOGRAPHIC RETENTION INDICES; QUANTITATIVE STRUCTURE PROPERTY RELATIONSHIPS; QUANTITATIVE STRUCTURE-RETENTION RELATIONSHIP; RELATIONSHIP MODEL; SEMI-EMPIRICAL; SEMI-EMPIRICAL ELECTROTOPOLOGICAL INDEX; STATIONARY PHASE;

KETONES;

EID: 77951074135     PISSN: 08869383     EISSN: 1099128X     Source Type: Journal    
DOI: 10.1002/cem.1303     Document Type: Article

References (42)

1. Kaliszan R. Quantitative Structure-Chromatographic Retention Relation-ships. Wiley: New York, 1987.
2. Kaliszan R. QSRR: quantitative structure-(chromatographic) retention relationships. Chem. Rev. 2007; 107: 3212-3246.
3. Hérberger K. Quantitative structure-(chromatographic) retention relationships. J. Chromatogr. A 2007; 1158: 273-305.
4. Guo W, Lu Y, Zheng XM. The predicting study for chromatographic retention index of saturated alcohols by MLR and ANN. Talanta 2000; 51: 479-488.
5. Peng CT. Prediction of retention indices of retention indices V. Influence of electronic effects and column polarity on retention index. J. Chromatogr. A 2002; 903: 117-143.
6. Mu L, Feng C, Xu L. Study on QSPR of Alcohols with a Novel Edge Connectivity Index mF. MATCH Commun. Math. Comput. Chem. 2006; 56: 217-230.
7. Ivanciuc T, Ivanciuc O. Quantitative structure-retention relationship study of gas chromatographic retention indices for halogenated compounds. Internet Electron. J. Mol. Des. 2002; 1: 94-107. http://www.biocempress.com
8. Liu F, Ling Y, Cao, Zhou N. Theoretical prediction of the Kovat's index for oxygen oxygen-containing organic compounds using novel topological indices. Anal. Chim. Acta 2007; 594: 279-289.
9. Beteringhe A, Radutiu AC, Culita DC, Mischie A, Spafiu F. Quantitative structure-retention relationship (qsrr) study for predicting gas chromatographic retention times for some stationary phases. QSAR Comb. Sci. 2008; 27: 996-1005.
10. Farkas O, Héberger K. Comparison of ridge regression, partial least-squares, pairwise correlation, forward-and best subset selection methods for prediction of retention indices for aliphatic alcohols. J. Chem. Inf. Model. 2005; 45: 339-346.
11. Ren Y, Liu H, Yao X, Liu M. Three-dimensional topographic index applied to the prediction of acyclic C5-C8 alkenes Kováts retention indices on polydimethylsiloxane and squalane columns. J. Chromatogr. A 2007; 1155: 105-111.
12. Ren B. Application of novel atom-type AI topological indices in the structure-property correlations. J. Mol. Struct. (Theochem) 2002; 586: 137-148
13. Ren B. Novel atomic-level-based AI topological descriptors: application to QSPR/QSAR modeling. J. Chem. Inf. Comput. Sci. 2002; 42: 858-868
14. Ren B. Novel atom-type AI indices for QSPR studies of alcohols. Comput. Chem. 2002; 26: 223-235
15. Kier LB, Hall LH, Farzer JW. An index of electrotopological state for atoms in molecules. J. Math. Chem. 1991; 7: 229-241
16. Randic M. Wiener-Hosoya index-a novel graph theoretical molecu-lar descriptor. J. Chem. Inf. Comp. Sci. 2004; 44: 373-377
17. Randic M. On interpretation of well-known topological indices. J.Chem. Inf. Comp. Sci. 2001; 41: 550-560
18. Heinzen VEF, Soares MF, Yunes RA. Semi-empirical topological method for prediction of the chromatographic retention of cis-and trans-alkene isomers and alkanes. J. Chromatogr. A 1999; 849: 495-506
19. Junkes BS, Amboni RDMC, Yunes RA, Heinzen VEF. Use of a semiempirical topological method to predict the chromato-graphic retention of branched alkenes. Chromatographia 2002; 55: 75-81.
20. Junkes BS, Amboni RDMC, Yunes RA, Heinzen VEF. Quantitative structure-retention relationships (QSRR), using the optimum semi-empirical topological index, for methyl-branched alkanes produced by insects. Chromatographia 2002; 55: 707-715.
21. Amboni RDMC, Junkes BS, Yunes RA, Heinzen VEF. Semi-empirical topological method for prediction of the chromatographic retention of esters. J. Mol. Struct. (Theochem) 2002; 579: 53-62
22. Amboni RDMC, Junkes BS, Yunes RA, Heinzen VEF. Quantitative structure-property relationship study of chromatographic retention indices and normal boiling points for oxo compounds using the semi-empirical topological method. J. Mol. Struct. (Theochem) 2002; 586: 71-80
23. Junkes BS, Amboni RDMC, Yunes RA, Heinzen VEF. Semi-empirical topological index: a novel molecular descriptor for quantitative structure-retention relationship studies. Internet Electron. J. Mol. Des. 2003; 2: 33-49.
24. Junkes BS, Amboni RDMC, Yunes RA, Heinzen VEF. Prediction of chromatographic retention of saturated alcohols on stationary phases of different polarity applying the novel semi-empirical topological index. Anal. Chim. Acta 2003; 477: 29-39.
25. Junkes BS, Amboni RDMC, Yunes RA, Heinzen VEF. Application of the semi-empirical topological index in the QSRR of aliphatic ketones and aldehydes on stationary phases of different polarity. J. Braz. Chem. Soc. 2004; 15: 183-189
26. Junkes BS, Arruda ACS, Yunes RA, Porto LC, Heinzen VEF. Semiempirical topological index: application to QSPR/QSAR modeling. J. Mol. Model. 2005; 11: 128-134.
27. Porto LC, Souza ES, Junkes BS, Yunes RA, Heinzen VEF. Semi-empirical topological index: development of QSPR/QSRR and optimization for alkylbenzenes. Talanta 2008; 76: 407-412.
28. Arruda ACS, Souza ES, Junkes BS, Yunes RA, Heinzen VEF. Semi-empirical topological index to predict properties of halogenated aliphatic compounds. J. Chemom. 2008; 22: 186-194
29. Souza ES, Junkes BS, Kuhnen CA, Yunes RA, Heinzen VEF. On a new semi-empirical electrotopological index for QSRR models. J. Chemom. 2008; 22: 378-384.
30. Souza ES, Kuhnen CA, Junkes BS, Yunes RA, Heinzen VEF. Modelling the semi-empirical electrotopological index in QSPR studies for aldehydes and ketones. J. Chemom. 2008; 23: 229-235
31. Souza ES, Kuhnen CA, Junkes BS, Yunes RA, Heinzen VEF. Quantitative structure-retention relationship modelling of esters on stationary phases of different polarity. J. Mol. Graph. Model. 2009; 28: 20-27.
32. Zang X, Lu P. Unified equation between Kováts indices on different stationary phases for select types of compounds. J. Chromatogr. A 1996; 731: 187-199
33. Pias JP, Gasco L. Gas-liquid chromatography on phenyl-substituted polysiloxane stationary phases, alcohols and alcohol benzoyl derivatives. Anal. Chim. Acta 1975; 75: 139-148.
34. Tarján G, Kiss Á, Kocsis G, Mészáros S, Takács JM. General contribution to the theory of retention index systems in gas-liquid chromatography: III. Contribution to the polarity of gas chromatographic stationary phases expressed by retention indices. J. Chromatogr. 1976; 119: 327-332.
35. Hyper Chem for Windows, Release 7.01, serial number 12-701-150170036, Hypercube, 2002.
36. Smith WB. Introduction to Theoretical Organic Chemistry and Molecular Modeling. VCW: New York, 1996.
37. Bredow T, Jug K. Theory and range of modern semiempirical mol-ecular orbital methods. Theor. Chem. Acc. 2005; 113: 1-14.
38. Kikuchi O. Systematic QSAR procedures with quantum chemical descriptors. Quant. Struct. Act. Relat. 1987; 6: 179-184.
39. MicroCal Origin version 5.0, 1997
40. TsarTM 3.3 for Windows, Oxford Molecular Ltd., 2000
41. Rohrschneider L. Eeine methode zur charakterisierung von gaschromato-graphischen trennflussigkeiten. J. Chromatogr. 1966; 22: 6-22
42. McReynolds WO. Characterization of some liquid phases. J. Chroma-togr. Sci. 1970; 8: 685-691