On topological indices, boiling points, and cycloalkanes

Journal of Chemical Information and Computer Sciences

Volumn 39, Issue 5, 1999, Pages 788-802

  Rücker, Gerta ^a   Rücker, Christoph ^a  

^a UNIVERSITY OF FREIBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0041037845     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci9900175     Document Type: Article

References (59)

1. (a) Katritzky, A. R.; Lobanov, V. S.; Karelson, M. Normal Boiling Points for Organic Compounds: Correlation and Prediction by a Quantitative Structure-Property Relationship. J. Chem. Inf. Comput. Sci. 1998, 38, 28-41.
2. (b) Ivanciuc, O.; Ivanciuc, T.; Balaban, A. T. Quantitative Structure-Property Relationship Study of Normal Boiling Points for Halogen-/Oxygen-/Sulfur-Containing Organic Compounds Using the CODESSA Program. Tetrahedron 1998, 54, 9129-9142.
3. Randić, M.; Mihalić, Z.; Nikolić, S.; Trinajstić, N. Graph-Theoretical Correlations - Artifacts or Facts? Croat. Chem. Acta 1993, 66, 411-434.
4. (a) Diudea, M. V.; Gutman, I. Wiener-Type Topological Indices. Croat. Chem. Acta 1998, 71, 21-51.
5. (b) Gutman, I.; Diudea, M. V. Correcting the Definition of Cluj Matrices. MATCH 1998, 37, 195-201.
6. (c) Lukovits, I.; Linert, W. Polarity-Numbers of Cycle-Containing Structures. J. Chem. Inf. Comput. Sci. 1998, 38, 715-719.
7. Hosoya, H.; Kawasaki, K.; Mizutani, K. Topological Index and Thermodynamic Properties. I. Empirical Rules on the Boiling Point of Saturated Hydrocarbons. Bull. Chem. Soc. Jpn. 1972, 45, 3415-3421.
8. Lukovits, I.; Linert, W. A Novel Definition of the Hyper-Wiener Index for Cycles. J. Chem. Inf. Comput. Sci. 1994, 34, 899-902.
9. Gautzsch, R.; Zinn, P. List Operations on Chemical Graphs. 5. Implementation of Breadth-First Molecular Path Generation and Application in the Estimation of Retention Index Data and Boiling Points. J. Chem. Inf. Comput. Sci. 1994, 34, 791-800.
10. Hermann, A.; Zinn, P. List Operations on Chemical Graphs. 6. Comparative Study of Combinatorial Topological Indexes of the Hosoya Type. J. Chem. Inf. Comput. Sci. 1995, 35, 551-560.
11. Lukovits, I. The Detour Index. Croat. Chem. Acta 1996, 69, 873-882.
12. Trinajstić, N.; Nikolić, S.; Lucić, B.; Amić, D.; Mihalić, Z. The Detour Matrix in Chemistry. J. Chem. Inf. Comput. Sci. 1997, 37, 631-638.
13. Rücker, G.; Rücker, C. Symmetry-Aided Computation of the Detour Matrix and the Detour Index. J. Chem. Inf. Comput. Sci. 1998, 38, 710-714.
14. Plavsić, D.; Soskić, M.; Daković, Z.; Gutman, I.; Graovac, A. Extension of the Z Matrix to Cycle-Containing and Edge-Weighted Molecular Graphs. J. Chem. Inf. Comput. Sci. 1997, 37, 529-534.
15. Das, A.; Dömötör, G.; Gutman, I.; Joshi, S.; Karmarkar, S.; Khaddar, D.; Khaddar, T.; Khadikar, P. V.; Popović, L.; Sapre, N. S.; Sapre, N.; Shirhatti, A. A Comparative Study of the Wiener, Schultz and Szeged Indices of Cycloalkanes. J. Serb. Chem. Soc. 1997, 62, 235-239.
16. (a) Diudea, M. V. Indices of Reciprocal Properties or Harary Indices. J. Chem. Inf. Comput. Sci. 1997, 37, 292-299.
17. (b) Diudea, M. V. Cluj Matrix Invariants. J. Chem. Inf. Comput. Sci. 1997, 37, 300-305.
18. (c) Diudea, M.; Katona, G.; Lukovits, I.; Trinajstić, N. Detour and Cluj-Detour Indices. Croat. Chem. Acta 1998, 71, 459-471.
19. Estrada, E. Spectral Moments of the Edge Adjacency Matrix in Molecular Graphs. 3. Molecules Containing Cycles. J. Chem. Inf. Comput. Sci. 1998, 38, 23-27.
20. For example: propylcyclobutane, ref 13b used 110, ref 14 100.6 °C; isopropylcyclohexane, ref 13b used 146, ref 7 154.6, refs 8 and 9 171.3 °C; 1,3-dimethylcyclohexane, ref 13a used 120, ref 13b 124.5 °C.
21. 10; prepared by ASTM Committee D-2 on Petroleum and Lubricants and API Research Project 44 on Hydrocarbons and Related Compounds: Philadelphia, PA, 1971 . Many of the latter bp values were used and printed (citing as data source the API Research Project 44, 1947-1991) in the following: Gakh, A. A.; Gakh, E. G.; Sumpter, B. G.; Noid, D. W. Neural Network-Graph Theory Approach to the Prediction of the Physical Properties of Organic Compounds. J. Chem. Inf. Comput. Sci. 1994, 34, 832-839. In the absence of evidence for the latter values being better than the former, we decided to use the original values from Rossini (1953).
22. 10; prepared by ASTM Committee D-2 on Petroleum and Lubricants and API Research Project 44 on Hydrocarbons and Related Compounds: Philadelphia, PA, 1971 . Many of the latter bp values were used and printed (citing as data source the API Research Project 44, 1947-1991) in the following: Gakh, A. A.; Gakh, E. G.; Sumpter, B. G.; Noid, D. W. Neural Network-Graph Theory Approach to the Prediction of the Physical Properties of Organic Compounds. J. Chem. Inf. Comput. Sci. 1994, 34, 832-839. In the absence of evidence for the latter values being better than the former, we decided to use the original values from Rossini (1953).
23. 10; prepared by ASTM Committee D-2 on Petroleum and Lubricants and API Research Project 44 on Hydrocarbons and Related Compounds: Philadelphia, PA, 1971 . Many of the latter bp values were used and printed (citing as data source the API Research Project 44, 1947-1991) in the following: Gakh, A. A.; Gakh, E. G.; Sumpter, B. G.; Noid, D. W. Neural Network-Graph Theory Approach to the Prediction of the Physical Properties of Organic Compounds. J. Chem. Inf. Comput. Sci. 1994, 34, 832-839. In the absence of evidence for the latter values being better than the former, we decided to use the original values from Rossini (1953).
24. ( 17) Rücker, G. ; Rücker, C. Counts of All Walks as Atomic and Molecular Descriptors. J. Chem. Inf. Comput. Sci. 1993, 33, 683-695.
25. (a) Diudea, M. V.; Minailiuc, O. M.; Katona, G. Novel Connectivity Descriptors Based on Walk Degrees. Croat. Chem. Acta 1996, 69, 857-871.
26. (b) Ivanciuc, O.; Diudea, M.; Khadikar, P. V. New Topological Matrices and Their Polynomials. Indian J. Chem., Sect. A 1998, 37A, 574-585.
27. Wieland, T.; Kerber, A.; Laue, R. Principles of Generation of Constitutional and Configurational Isomers. J. Chem. Inf. Comput. Sci. 1996, 36, 413-419.
28. Hendrickson, J. B.; Huang, P.; Toczko, A. G. Molecular Complexity: A Simplified Formula Adapted to Individual Atoms. J. Chem. Inf. Comput. Sci. 1987, 27, 63-67.
29. Razinger, M.; Chretien, J. R.; Dubois, J. E. Structural Selectivity of Topological Indexes in Alkane Series. J. Chem. Inf. Comput. Sci. 1985, 25, 23-27.
30. Randić, M.; Hansen, P. J.; Jurs, P. C. Search for Useful Graph Theoretical Invariants of Molecular Structure. J. Chem. Inf. Comput. Sci. 1988, 28, 60-68.
31. (a) Randić, M. Comparative Regression Analysis: Regressions Based on a Single Descriptor. Croat. Chem. Acta 1993, 66, 289-312.
32. (b) Bhattacharjee, S.; Dasgupta, P. Molecular Property Correlation in Alkanes With Geometric Volume. Comput. Chem. 1994,18, 61-71.
33. (c) Nikolić, S.; Trinajstić, N.; Mihalic, Z. The Wiener Index: Development and Applications. Croat. Chem. Acta 1995, 68, 105-129.
34. (a) Wiener, H. Structural Determination of Paraffin Boiling Points. J. Am. Chem. Soc. 1947, 69, 17-20.
35. (b) Kirby, E. C. Sensitivity of Topological Indices to Methyl Group Branching in Octanes and Azulenes, or What Does a Topological Index Index? J. Chem. Inf. Comput. Sci. 1994, 34, 1030-1035.
36. Randić, M. Linear Combinations of Path Numbers as Molecular Descriptors. New J. Chem. 1997, 21, 945-951.
37. Medeleanu, M.; Balaban, A. T. Real-Number Vertex Invariants and Schultz-Type Indices Based on Eigenvectors of Adjacency and Distance Matrixes. J. Chem. Inf. Comput. Sci. 1998, 38, 1038-1047.
38. 2Z and the Hosoya Z Index. J. Chem. Inf. Comput. Sci. 1996, 36, 1118-1122.
39. Randić, M.; Trinajstić, N. Isomeric Variations in Alkanes: Boiling Points of Nonanes. New J. Chem. 1994, 18, 179-189.
40. Lucić, B.; Trinajstic, N. New Developments in QSPR/QSAR Modeling Based on Topological Indices. SAR QSAR Environ. Res. 1997, 7, 45-62.
41. Bonchev, D. Novel Indices for the Topological Complexity of Molecules. SAR QSAR Environ. Res. 1997, 7, 23-43.
42. Ren, B. A New Topological Index for QSPR of Alkanes. J. Chem. Inf. Comput. Sci. 1999, 39, 139-143.
43. Toropov, A.; Toropova, A.; Ismailov, T.; Bonchev, D. 3D Weighting of Molecular Descriptors for QSPR/QSAR by the Method of Ideal Symmetry (MIS). 1. Application to Boiling Points of Alkanes. J. Mol. Struct. (Theochem) 1998, 424, 237-247.
44. (a) Needham, D. E.; Wei, I.-C.; Seybold, P. G. Molecular Modeling of the Physical Properties of the Alkanes. J. Am. Chem. Soc. 1988, 110, 4186-4194.
45. (b) Basak, S. C.; Niemi, G. J.; Veith, G. D. Predicting Properties of Molecules Using Graph Invariants. J. Math. Chem. 1991, 7, 243-272.
46. Toropov, A. A.; Toropova, A. P.; Ismailov, T. T.; Voropaeva, N. L.; Ruban, I. N. Extended Molecular Connectivity: Prediction of Boiling Points of Alkanes. J. Struct. Chem. (Engl. Transi.) 1997, 38, 965-969.
47. Basak, S. C.; Grunwald, G. D.; Niemi, G. J. In From Chemical Topology to Three-Dimensional Geometry; Balaban, A. T., Ed.; Plenum: New York, 1997; Chapter 4, p 78.
48. (a) Estrada, E.; Guevara, N.; Gutman, I. Extension of Edge Connectivity Index. Relationship to Line Graph Indices and QSPR Applications. J. Chem. Inf. Comput. Sci. 1998, 38, 428-431.
49. (b) Estrada, E. Generalized Spectral Moments of the Iterated Line Graphs Sequence. A Novel Approach to QSPR Studies. J. Chem. Inf. Comput. Sci. 1999, 39, 90-95.
50. Estrada, E.; Ivanciuc, O.; Gutman, I.; Gutierrez, A.; Rodriguez, L. Extended Wiener Indices. A New Set of Descriptors for Quantitative Structure-Property Studies. New J. Chem. 1998, 819-822.
51. Yang, Y.-Q.; Xu, L.; Hu, C.-Y. Extended Adjacency Matrix Indices and Their Applications. J. Chem. Inf. Comput. Sci. 1994, 34, 1140-1145.
52. Liu, S.; Cao, C.; Li, Z. Approach to Estimation and Prediction for Normal Boiling Point (NBP) of Alkanes Based on a Novel Molecular Distance-Edge (MDE) Vector, λ. J. Chem. Inf. Comput. Sci. 1998, 38, 387-394.
53. Ferris, S. W. Handbook of Hydrocarbons, Academic Press: New York, 1955.
54. Varushchenko, R. M.; Pashchenko, L. L.; Druzhinina, A. I. Enthalpies of Vaporization of Some Mono- and Polycyclic Hydrocarbons. Russ. J. Phys. Chem. (Engl. Transl.) 1996, 70, 208-211.
55. (a) Mizutani, K.; Kawasaki, K.; Hosoya, H. Tables of Non-Adjacent Numbers, Characteristic Polynomials and Topological Indices. I. Tree Graphs. Nat. Sci. Rep. Ochanomizu Univ. 1971, 22, 39-58.
56. (b) Kawasaki, K.; Mizutani, K.; Hosoya, H. Tables of Non-Adjacent Numbers, Characteristic Polynomials and Topological Indices. II. Mono- and Bicyclic Graphs. Nat. Sci. Rep. Ochanomizu Univ. 1971, 22, 181-214.
57. (a) Manoharan, M.; Balakrishnarajan, M. M.; Venuvanalingam, P.; Balasubramanian, K. Topological Resonance Energy Predictions of the Stability of Fullerene Clusters. Chem. Phys. Lett. 1994, 222, 95-100.
58. 50. J. Chem. Inf. Comput Sci. 1994, 34, 421-427.
59. Randić, M.; Wilkins, C. L. Graph Theoretical Ordering of Structures as a Basis for Systematic Searches for Regularities in Molecular Data. J. Phys. Chem. 1979, 83, 1525-1540.