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Abstract
In this work, we have made an attempt to derive a novel information theoretic topological index, net-sign identity information index, Ie
from the molecular electronic structure, proposed by Lee et al. [S.-L. Lee, R.R. Lucchese, S.-Y. Chu, Chem. Phys. Lett., 137 (1987) 279]
in chemical graph theory. The performance of the net-sign identity information index along with the square root of the bonding infor-
p p
mation index, Ib and the square root of net-sign identity information index, Ie have been compared with the most widely used molec-
ular descriptors: Wiener index (W), Randics connectivity index (v) and Balabans distance sum connectivity index (J) in QSPR modeling.
2008 Elsevier B.V. All rights reserved.
0009-2614/$ - see front matter 2008 Elsevier B.V. All rights reserved.
doi:10.1016/j.cplett.2008.01.055
134 P.K. Sahu, S.-L. Lee / Chemical Physics Letters 454 (2008) 133138
Table 2
Observed values and predicted values for the physical properties of 12 saturated hydrocarbons (alkanes)
p
No. Name Type Ie MV MV BP BP MR MR PC PC TC TC
(obs.) (pred.) (obs.) (pred.) (obs.) (pred.) (obs.) (pred.) (obs.) (pred.)
1 C2 G21 0.000 35.522 42.505 88.63 64.56 48.2 43.82 32.27 66.44
2 C3 G32 5.655 48.051 49.300 42.07 44.75 42.01 41.61 96.8 92.02
3 nC4 G43 13.742 61.722 59.017 0.5 16.42 37.47 38.45 152.01 128.59
4 2MC3 G0 43 13.447 61.767 58.663 11.73 17.45 36.00 38.57 134.98 127.26
5 nC5 G54 23.322 74.122 70.528 36.07 17.14 25.265 25.502 33.31 34.71 196.62 171.92
6 2MC4 G0 54 24.560 75.032 72.016 27.85 21.47 25.292 25.899 32.9 34.23 187.8 177.52
7 22MMC3 G00 54 22.626 73.917 69.692 9.50 14.69 25.724 25.279 31.57 34.98 160.6 168.77
8 nC6 G65 37.667 84.523 87.765 68.74 67.39 29.906 30.102 29.92 29.11 234.7 236.80
9 2MC5 G0 65 33.547 85.259 82.815 60.27 52.95 29.945 28.781 29.95 30.72 224.9 218.17
10 3MC5 G00 65 37.465 85.335 87.522 63.28 66.68 29.801 30.037 30.83 29.19 231.2 235.88
11 23MMC4 GIV65 37.465 84.447 87.522 57.98 66.68 29.81 30.037 30.99 29.19 227.1 235.88
12 22MMC4 GV65 37.465 85.174 87.522 49.74 66.68 29.935 30.037 30.67 29.19 216.2 235.88
M stands for methyl.
Units: MV (L/mol), BP (C), MR (m3/mol), PC (atm), TC (C).
Table 3
Observed values and predicted values for the physical properties of 13 unsaturated hydrocarbons (akenes)
p
No. Name Type Ie MV (obs.) MV (pred.) BP (obs.) BP (pred.) MR (obs.) MR (pred.)
1 Ethylene G21 0.000 31.203 37.296 103.7 74.4
2 Propene G32 5.655 43.031 44.294 47.4 53.2
3 1-Butene G43 13.742 55.659 54.299 6.3 22.9
4 2-M-propene G43 13.447 60.504 53.935
5 1-Pentene G54 23.322 67.473 66.153 29.9 12.8 24.858 25.332
6 2-M-1-Butene G54 24.559 67.407 67.684 31.2 17.5
7 3-M-1-Butene G54 24.559 71.324 67.684 20.1 17.5
8 1-Hexene G65 37.667 81.738 83.902 63.3 66.5 29.208 29.915
9 3-M-1-pentene G65 33.547 81.181 78.805 54.1 51.1 29.485 28.599
10 2-M-1-pentene G65 37.465 84.001 83.652 60.7 65.7 29.398 29.851
11 2-E-1-Butene G65 33.547 80.516 78.805 64.7 51.1 29.391 28.599
12 2,3-MM-1-butene GIV65 37.465 80.351 83.652 55.7 65.7 30.063 29.851
13 3,3-MM-1-butene GV65 37.465 79.432 83.652 41.2 65.7 29.598 29.851
M and E stands for methyl and ethyl, respectively.
Units: MV (L/mol), BP (C), MR (m3/mol).
136 P.K. Sahu, S.-L. Lee / Chemical Physics Letters 454 (2008) 133138
[10] H. Wiener, J. Am. Chem. Soc. 69 (1947); [21] S.-L. Lee, Y.-N. Yeh, Chem. Phys. Lett. 171 (1990) 385.
J. Chem. Phys. 15 (1947) 766. [22] S.-L. Lee, F.-Y. Li, F. Lin, Int. J. Quantum Chem. 39 (1991) 59.
[11] A.T. Balaban, Chem. Phys. Lett. 89 (1982) 399. [23] S.-L. Lee, Y.-L. Luo, E.B. Sagan, Y.-N. Yeh, Int. J. Quantum Chem.
[12] M. Randic, J. Am. Chem. Soc. 97 (1975) 6609. 41 (1992) 105.
[13] L.B. Kier, L.H. Hall, W.J. Murray, M. Randic, J. Pharm. Sci. 64 [24] S.-L. Lee, Theor. Chim. Acta 81 (1992) 185.
(1975) 1971. [25] S.-L. Lee, Y.-N. Yeh, J. Math. Chem. 13 (1993) 75.
[14] D. Bonchev, N. Trinajstic, Int. J. Quantum Chem. Symp. 12 (1978) [26] I. Gutman, S.-L. Lee, Y.-N. Yeh, Chem. Phys. Lett. 191 (1992) 87.
293; [27] I. Gutman, S.-L. Lee, Y.-N. Yeh, Int. J. Quantum Chem. 49 (1994)
D. Bonchev, A.T. Balaban, A. Mekenyan, J. Chem. Inf. Comput. Sci. 87.
20 (1980) 106. [28] P. K. Sahu, S.-L. Lee, submitted for publication.
[15] I. Gutman, N. Trinajstic, J. Chem. Phys. 62 (1975) 3339. [29] Lord Kelvin, Baltimore Lecture on Molecular Dynamics and the
[16] H. Hosoya, Int. J. Quantum Chem. 6 (1972) 801. Wave Theory of Light, C.J. Clay, London, 1904, pp. 439, 619.
[17] S.C. Basak, B.D. Gute, G.D. Grunwald, J. Chem. Inf. Comput. Sci. [30] N.E. Diane, I.C. Wei, P.G. Seybold, J. Am. Chem. Soc. 110 (1988)
36 (1996) 1054. 4186.
[18] S.-L. Lee, R.R. Lucchese, S.-Y. Chu, Chem. Phys. Lett. 137 (1987) [31] L. Xu, C. Hu, Application of Chemical Graphs, Scientic Press,
279. Beijing, 2000.
[19] P.K. Sahu, S.-L. Lee, Chem. Phys. Lett. 396 (2004) 465. [32] L.S. Wang, Z.L. Zhi, Molecular Connectivity and Molecular Struc-
[20] S.-L. Lee, I. Gutman, Chem. Phys. Lett. 157 (1989) 229. ture Activity, Chinese Environment Science Press, Beijing, 1992.