From molecular connectivity indices to semiempirical connectivity terms: Recent trends in graph theoretical descriptors

Chemical Reviews

Volumn 100, Issue 10, 2000, Pages 3827-3858

  Pogliani, Lionello ^a  

^a UNIVERSITY OF CALABRIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

ALGORITHMS; AMINO ACIDS; ENTHALPY; GRAPH THEORY; HEURISTIC METHODS; ISOMERIZATION; MATHEMATICAL MODELS; MELTING; MOLECULAR DYNAMICS; MOLECULAR STRUCTURE; ORGANIC SOLVENTS; SOLUBILITY;

GRAPH MASS INDEX; PSEUDOGRAPHS;

MOLECULAR PHYSICS;

EID: 0034299377     PISSN: 00092665     EISSN: None     Source Type: Journal    
DOI: 10.1021/cr0004456     Document Type: Article

References (126)

1. Rosen, K. H. Discrete mathematics and its applications; McGraw-Hill: New York, 1995. Harary, F. Graph Theory, 2nd printing; Addison-Wesley: Reading, MA, 1971.
2. Rosen, K. H. Discrete mathematics and its applications; McGraw-Hill: New York, 1995. Bamberg, O.; Sternberg, S. A Course in Mathematics for Students of Physics; Cambridge University Press: Cambridge, 1990; Vol. 2. Bamberg, O.; Sternberg, S. A Course in Mathematics for Students of Physics; Cambridge University Press: Cambridge, 1990; Vol. 2.
3. Rosen, K. H. Discrete mathematics and its applications; McGraw-Hill: New York, 1995. Bamberg, O.; Sternberg, S. A Course in Mathematics for Students of Physics; Cambridge University Press: Cambridge, 1990; Vol. 2. Harary, F. Graph Theory, 2nd printing; Addison-Wesley: Reading, MA, 1971. Harary, F. Graph Theory, 2nd printing; Addison-Wesley: Reading, MA, 1971. J. Chem. Inf.Comput. Sci. 1985 25, 334.
4. Chemical applications of Graph theory; Balaban, A. T., Ed.; Academic Press: London, 1986;
5. Chemical applications of Graph theory; Balaban, A. T., Ed.; Academic Press: London, 1986; J. Chem. Inf.Comput. Sci. 1985 25, 334. J. Chem. Inf.Comput. Sci. 1985 25, 334.
6. Kier, L. B.; Hall L. H. Molecular connectivity in structure-activity analysis; Wiley: New York, 1986.
7. Trinajstić, N. Chemical graph theory, 2nd ed.; CRC Press: Boca Raton, 1992.
8. Reinhard, M.; Drefahl, A. Handbook for Estimating Physicochemical Properties of Organic Compounds; Wiley: New York 1999.
9. Rouvray, D. H. J. Mol. Struct.(THEOCHEM) 1989, 185, 187.
10. Turro, N. J. Angew. Chem., Int. Ed. Engl. 1986, 25, 882.
11. Randić, M.; Trinajstic, N. Croat. Chem. Acta 1994, 67, 1.
12. Randić, M. J. Am. Chem. Soc. 1975, 97, 6609-6615.
13. Kier, L. B.; Hall, L. H.; Murray, W. J.; Randić, M. J. Pharm. Sci. 1975, 64, 1971.
14. Kier, L. B.; Hall, L. H.; Murray, W. J. J. Pharm. Sci. 1975, 64, 1974.
15. Hall, L. H.; Kier, L. B. J. Pharm. Sci. 1976, 65, 1806.
16. Kier, L. B.; Hall, L. H. Molecular Connectivity in Chemistry and Drug Research; Academic Press: New York, 1976.
17. Hall, L. H.; Kier, L. B. Tetrahedron 1977, 33, 1953.
18. Kier, L. B.; Hall, L. H. J. Pharm. Sci. 1981, 70, 583.
19. Kier, L. B. J. Pharm. Sci. 1981, 70, 930.
20. Edward, J. T. Can. J. Chem. 1982, 60, 480.
21. Aravindakshan, P. Mater. Chem. Phys. 1983, 8, 171.
22. (191 Mekenyan, O.; Bonchev, D.; Balaban, A. T. Chem. Phys. Lett. 1984, 109, 85.
23. Seybold, P. G.; May, M.; Bagal, A. U. J. Chem. Educ. 1987, 64, 575.
24. Randić, M. Int. J. Quantum Chem.: Quantum Biol. Symp. 1988, 15, 201.
25. Randić, M.; Hansen, P. J.; Jurs, P. C. J. Chem. Inf. Comput. Sci. 1988, 28, 60.
26. Hansen P. J.; Jurs P. C. J. Chem. Educ. 1988, 65, 574.
27. Basak, S. C.; Magnuson, V. R.; Niemi G. J.; Regal, R. R. Discr. Appl. Math. 1988, 19, 17.
28. Needham, D. E.; Wei I.-C.; Seybold, P. G. J. Am. Chem. Soc. 1988, 110, 4186.
29. Randić, M. N. J. Chem. 1991, 15, 517.
30. Randić, M. J. Chem. Inf. Comput. Sci. 1991, 31, 311.
31. Randić, M. Croat. Chem. Acta 1991, 64, 43.
32. Randić, M. J. Mol. Struct. (THEOCHEM) 1991, 233, 45.
33. Basak, S. C.; Niemi, G. J.; Veith, G. D. J. Math. Chem. 1991, 7, 243.
34. Stanton, D. T.; Jurs, P. C. J. Chem. Inf. Comput. Sci 1992, 32, 109.
35. Maier, B. J. J. Chem. Inf. Comput. Sci. 1992, 32, 87.
36. Mihalić, Z.; Trinajstić, N. J. Chem. Ed. 1992, 69, 701.
37. Balaban, T. A.; Kier, L. B.; Joshi, N. Match (Comm. Math. Chem.) 1992, 28, 13.
38. Mihalić, Z.; Nikolić, S.; Trinajstić, N. J. Chem. Inf. Comput. Sci. 1992, 32, 28.
39. Kier, L. B.; Hall, L. H.; Frazer, J. W. J. Chem. Inf. Comput. Sci. 1993, 33, 3, 143.
40. Hall, L. H.; Kier, L. B.; Frazer, J. W. J. Chem. Inf. Comput. Sci. 1993, 33, 148,
41. Basak, S. C.; Grunwald, G. D. SAR QSAR Environ. Res. 1994, 2, 289.
42. Balaban, A. T.; Bertelsen, S. Match (Comm. Math. Chem.) 1984, 30, 55.
43. Balaban, A. T.; Basak, S. C.; Colburn T.; Grunwald, G. D. J. Chem. Inf. Comput. Sci. 1994, 34, 1118.
44. Randić, M. Int. J. Quantum Chem.: Quantum Biol. Symp. 1994, 21, 215.
45. Galvez, J.; Garcia, R.; Salbert, M. T.; Soler R. J. Chem. Inf. Comput. Sci. 1994, 34, 520.
46. Galvez, J.; Garcia-Domenech R.; de Julian-Ortiz, J. V.; Soler, R. J. Chem. Inf. Comput. 1995, 35, 272.
47. Lucić, B.; Nikolić, S.; Trinajstić, N.; Juretić, D.; Jurić, A. Croat. Chem. Acta 1995, 68, 435.
48. Basak, S. C.; Grunwald, G. D. New J. Chem. 1995, 19, 231.
49. Estrada, E. J. Chem. Inf. Comput. Sci. 1995, 35, 31.
50. Galvez, J.; Garcia-Domenech, R.; De Gregorio Alapont, C.; de Julian-Ortiz, J. V.; Popa, L. J. Mol. Graphics 1996, 14, 272.
51. Garcia-Domenech, R.; de Gregorio Alapont C.; de Julian-Ortiz, J. V.; Galvez, J. Bioorg. Med. Chem. Lett. 1997, 7, 567.
52. Galvez, J. J. Mol. Struct. (THEOCHEM) 1998, 429, 255.
53. Estrada, E. J. Chem. Inf. Comput. Sci. 1998, 38, 23.
54. Kuanar, M.; Mishra, B. K. Bull. Chem. Soc. Jpn. 1998, 71, 191.
55. Katritzky, A. R.; Mu, L. J. Chem. Inf. Comput. Sci. 1998, 38, 28, 293, and 300.
56. Basak, S. C.; Gute, B. D. SAR QSAR Environ. Res. 1999, 10, 1.
57. Trinajstić, N.; Mihalić, Z.; Harris, F. E. Int. J. Quantum Chem.: Quantum Chem. Symp. 1994, 28, 525.
58. Pogliani, L. J. Pharm. Sci. 1992, 81, 334 and 967.
59. Pogliani, L. Comput. Chem. 1993, 17, 283.
60. Pogliani, L. J. Phys. Chem. 1993, 97, 6731.
61. Pogliani, L. J. Chem. Inf. Comput. Sci. 1994, 34, 801.
62. Pogliani, L. J. Phys. Chem. 1994, 98, 1494.
63. Pogliani, L. Amino Acids 1995, 9, 217.
64. Pogliani, L. J. Phys. Chem. 1995, 99, 925.
65. Pogliani, L. J. Chem. Inf. Comput. Sci. 1998, 36, 1082.
66. Pogliani, L. Croat. Chem. Acta 1996, 69, 95.
67. Pogliani, L. Croat. Chem. Acta 1997, 70, 803.
68. Pogliani, L. J. Phys. Chem. 1996, 100, 18065.
69. Pogliani, L. Med. Chem. Res. 1997, 7, 380.
70. Pogliani, L. Amino Acids 1997, 13, 237.
71. Pogliani, L. J. Chem. Inf. Comput. Sci. 1999, 39, 104.
72. Pogliani, L. J. Mol. Struct. (THEOCHEM) 1999, 466, 1.
73. Pogliani, L. J. Phys. Chem. 1999, 103, 1598.
74. Pogliani, L. The Concept of Graph Mass in Molecular Graph Theory. A Case in Data Reduction Analysis. In QSAR studies by Molecular Descriptors; Diudea, M., Ed.; Nova Science Publishers Inc.: New York, 2000.
75. Hosoyea, H. Bull. Chem. Soc. Jpn. 1971, 44, 2332.
76. Smolenski, E. A. Russ. J. Phys. Chem. 1964, 38, 700.
77. Balaban A. T. Chem. Phys. Lett. 1982, 89, 399.
78. Brown, R. D.; Martin, Y. C. SAR QSAR Environ. Res. 1998, 8, 23.
79. Cumming, D. J.; Andrews, C. W.; Bentley, J. A.; Cory, M. J. Chem. Inf. Comput. Sci. 1996, 36, 750.
80. Cheng, C.; Maggiora, G.; Lajiness, M.; Johnson, M. J. Chem. Inf. Comput. Sci. 1996, 36, 909.
81. Zheng, W.; Cho, S. J.; Tropsha, A. J. Chem. Inf. Comput. Sci. 1998, 38, 252 and 259.
82. Randić, M.; Jerman-Blazic, B.; Trinajstic, N. Comput. Chem. 1990, 14, 237.
83. Randić, M. J. Quantum Chem.: Quantum Biol. Symp. 1988, 15, 201.
84. Randić, M. Croat. Chem. Acta 1993, 66, 289.
85. Lucić, B.; Trinajstić, N. SAR QSAR Environ. Res. 1997, 7, 45.
86. Kier, L. B.; Hall, L. H. Molecular Connectivity in Chemistry and Drug Research ; Academic Press: New York, 1976.
87. Bridgam, P. W. Dimensional Analysis; Yale University Press: New Haven, 1931.
88. Berberan-Santos, M. N.; Pogliani, L. J. Math. Chem. 1999, 26, 255.
89. Randić, M. J. Chem. Inf. Comput. Sci. 1997, 37, 672.
90. Kier, L. B.; Hall, L. H. J. Pharm. Sci. 1981, 70, 583.
91. Chang, R. Physical Chemistry with Applications to Biological Systems; McMillan: New York, 1977; pp 357-361.
92. nd ed; Weast, C. R., Ed.-in-Chief.; Boca Raton, FL, 1984-1985; pp C-724-C-727.
93. CRC Handbook of chemistry and physics, 72nd ed; Lide, R. D., Ed.-in-Chief.; Boca Raton, FL, 1991-1992; pp 7-1-7-3.
94. CRC Handbook of Chemistry and Physics, 74th ed.; Lide, R. D., Ed.-in-Chief.; Boca Raton, FL, 1993-1994; pp 6-148-6-155.
95. Nakashima, N.; Suzuki E.-I, Appl. Spectrosc. Rev. 1984, 20, 1.
96. Ladik, J.; Appel, K. Theor. Chim. Acta 1966, 4, 132.
97. Xu, L.; Wang, H. W.; Su, Q. Comput. Chem. 1992, 16, 187 and 195.
98. Atkins, P. W. Physical Chemistry; Oxford University Press: Oxford, 1990; p 933.
99. Bruker Almanac; Bruker Scientific Instruments: Rheinstetten, Germany, 1986; pp 106-107.
100. Aldrich Solvents; Aldrich Chemical Co., Inc.: Milwakee, WI, 1995; p 9.
101. Gilman, J. J. J. Chem. Educ. 1999, 76, 1330.
102. Standard, J. M.; Clark, B. K. J. Chem. Educ. 1999, 76, 1363.
103. Laing, M. Educ. Chem. 1993, 30, 160.
104. Myers, R. T. J. Phys. Chem. 1979, 83, 294.
105. Rich, R. L. Bull. Chem. Soc. Jpn. 1993, 66, 1065.
106. Hansen, P. J.; Jurs, P. C. Anal. Chem. 1987, 59, 2322.
107. Carlton, T. S. J. Chem. Inf. Comput. Sci. 1998, 38, 158.
108. From Chemical Topology to Three-Dimensional Geometry; Balaban, A. T., Ed.; Plenum Press: New York, 1997.
109. Devillers, J.; Balaban, A. T. Topological Indices and Related Descriptors in QSAR and QSPR; Gordon and Breach: UK, 1999.
110. Basak, S.; Balaban, T.; Grunwald, G. D.; Gute, B. D. J. Chem. Inf. Comput. Sci. 2000, 40, 891.
111. Gutman, I.; Popovic, Lj.; Estrada, E.; Bertz, S. H. ACH-Models Chem. 1998, 135, 147.
112. Todeschini, R.; Consonni, V. Handbook of Molecular Descriptors; Wiley: New York, in press.
113. Kier, L. B.; Hall, L. H. J. Chem. Inf. Comput. Sci. 2000, 40, 792.
114. Randić, M. Chemom. Intel. Lab. Syst. 1991, 10, 213.
115. Randić, M. J. Comput. Chem. 1991, 12, 970.
116. Randić, M.; Dobrowolski, J. Sz. Int. J. Quantum Chem. 1998, 70, 1209.
117. Randić, M. Topological Indices. In The Encyclopedia of Computational Chemistry; Schleyer, P. V. R., Allinger, N. L., Clark, T., Gasteiger, J., Kollman, P. A., Schaefer, H. F., III, Schreiner, P. R., Eds.; Wiley: Chichester, 1998; pp 3018-3032.
118. Randić, M.; Basak, S. C.; Mills, D.; Pogliani, L. New J. Chem., submitted for publication.
119. Amić, D.; Beslo, D.; Lucić, B.; Nikolić, S.; Trinajstić, N. J. Chem. Inf. Comput. Sci. 1998, 38, 819.
120. Burden, F. R.; Winkler, D. A. J. Chem. Inf. Comput. Sci. 1999, 39, 236.
121. Randić, M.; Basak, S. C. J. Chem. Inf. Comput. Sci. 1999, 39, 26 1.
122. Basak, S.; Nikolic, S.; Trinajstić, N.; Amic, D.; Beslo, D. J. Chem. Inf. Comput. Sci. 2000, 40, 927.
123. Kier, L. B.; Hall, L. H. Molecular Structure Description. The Electrotopological State; Academic Press: New York, 1999.
124. Temkin, O. N.; Zeigarnik, A. V.; Bonchev, D. Chemical Reaction Networks; CRC Press: New York, 1996.
125. Grassy, G.; Calas, B.; Yasri, A.; Lahana, R.; Woo, J.; Iyer, S.; Kaczorek, M.; Floc'h R.; Buelow, R. Nat. Biotechol. 1998, 16, 748.
126. Randić, M. Similarity Methods of Interest in Chemistry. In Mathematical Methods in Contemporary Chemistry; Kuchanov, I. S., Ed.; Gordon & Breach: Amsterdam, 1996; pp 1-100.