Bulletin of the Korean Chemical Society

Korean Chemical Society (대한화학회)
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Highly Correlating Distance/Connectivity-Based Topological Indices. 1:QSPR Studies of Alkanes

  • Published : 2004.02.20
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Abstract

Some new topological indices based on the distance matrix and Randic connectivity (as graph invariants) are proposed. The calculation of these indices is simple and they have good discriminating ability toward alkanes. Incorporating the number of carbon atoms to one of the calculated indices gives a highly correlating topological index (Sh index) which found to correlate with selected physicochemical properties of wide range of alkanes, specially, their boiling points. Most of the investigated properties are well modeled (with $r^2$> 0.99) by the Sh index. Meanwhile, the resulting regressions were compared with the results based on the well-established Randic and newly reported Xu indices and, in most cases, better results were obtained by the Sh index. Moreover, multiple linear regression analysis of the alkane properties via calculated indices gives highly correlating models with low standard errors.

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References

  1. Turro, N. J. Angew. Chem. Int. Edit. Engl. 1986, 25, 882-901. https://doi.org/10.1002/anie.198608821
  2. Gilabert, L. E.; Sagrado, S.; Villanueva-Camanas, R. M.; Medina-Hernandes, M. J. Anal. Chem. 1998, 70, 28-34. https://doi.org/10.1021/ac970464o
  3. Li, H.; Xu, L.; Guo, M.; Su, Q. Talanta 1997, 44, 203-211. https://doi.org/10.1016/S0039-9140(96)02034-6
  4. Viswanadhan, V. N.; Mueller, G. A.; Basak, S. C.; Weinstein, J. N.J. Chem. Inf. Comp. Sci. 2001, 41, 505-511. https://doi.org/10.1021/ci000072+
  5. Agatonovic-Kustrin, S.; Tacker, L. G.; Zecevic, M.; Zivanovic, L.J. Anal. Chim. Acta 2000, 418, 181-195. https://doi.org/10.1016/S0003-2670(00)00963-6
  6. Shamsipur, M.; Hemmateenejad, B.; Akhond, M.; Sharghi, H.Talanta 2001, 54, 1113-1120. https://doi.org/10.1016/S0039-9140(01)00374-5
  7. Mihalic, Z.; Trinajistic, N. J. Chem. Educ. 1992, 69, 701-712. https://doi.org/10.1021/ed069p701
  8. Balaban, A. T. J. Chem. Inf. Comput. Sci. 1985, 25, 334-343. https://doi.org/10.1021/ci00047a033
  9. Balaban, A. T. J. Chem. Inf. Comput. Sci. 1995, 35, 339-350. https://doi.org/10.1021/ci00025a001
  10. Randic, M. J. Am. Chem. Soc. 1975, 97, 6609-6615. https://doi.org/10.1021/ja00856a001
  11. Wiener, H. J. Am. Chem. Soc. 1947, 69, 17-20. https://doi.org/10.1021/ja01193a005
  12. Hosoya, H. Bull. Chem. Soc. Jpn. 1971, 44, 2332-2339. https://doi.org/10.1246/bcsj.44.2332
  13. Balaban, A. T. Chem. Phys. Lett. 1982, 89, 399-404. https://doi.org/10.1016/0009-2614(82)80009-2
  14. Schultz, H. P. J. Chem. Inf. Comput. Sci. 1989, 29, 227-228. https://doi.org/10.1021/ci00063a012
  15. Plavsic, D.; Nikolic, S.; Trinajistic, N. J. Math. Chem. 1993, 12,235-250. https://doi.org/10.1007/BF01164638
  16. Kier, L. B.; Hall, L. H. Molecular Connectivity in Chemistry andDrug Research; Academic Press: New York, 1976.
  17. Yao, Y. Y.; Xu, L.; Yuan, X. S. Acta Chim. Sinica (in Chinese)1996, 54, 533-538.
  18. Ren, B. J. Chem. Inf. Comput. Sci. 1999, 39, 139-143. https://doi.org/10.1021/ci980098p
  19. Zhao, Y. H.; Yang, L. H.; Wang, L. S. Bull. Environ. Contam.Toxicol. 1996, 57, 242-249. https://doi.org/10.1007/s001289900182
  20. Smeeks, F. C.; Jurs, P. C. Anal. Chim. Acta 1990, 233, 111-119. https://doi.org/10.1016/S0003-2670(00)83466-2
  21. Malinowsky, E. R. Factor Analysis in Chemistry; John Wiley:New York, 1991.
  22. Rechsteiner, C. E. Handbook of Chemical Property EstimationMethods; Lyman, W. L.; Reehl, W. E.; Rosenblatt, D. H., Eds;McGraw Hill: New York, 1982.
  23. Kartitzky, A. R.; Mu, L.; Lobanov, V. S.; Karelson, M. A. J. Phys.Chem. 1996, 100, 10400-10407. https://doi.org/10.1021/jp953224q
  24. Fisher, C. H. Chem. Eng. 1989, 96, 157-158.
  25. Satyanarayana, K.; Kakati, M. C. Fire Mater. 1991, 15, 97-100. https://doi.org/10.1002/fam.810150208
  26. Randic, M.; Guo, X. F.; Oxley, T.; Krishnapriyan, H. J. Chem. Inf.Comput. Sci. 1993, 33, 709-716. https://doi.org/10.1021/ci00015a008
  27. Randic, M.; Guo, X. F.; Oxley, T.; Krishnapriyan, H. J. Chem. Inf.Comput. Sci. 1993, 33, 709-716. https://doi.org/10.1021/ci00018a022
  28. J. Chem. Inf. Comput. Sci. v.34 Randic, M.;Guo, X. F.;Oxley, T. https://doi.org/10.1021/ci00018a022

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