All acyclic hydrocarbons: Formula periodic table and property overlap plots via chemical combinatorics

New Journal of Chemistry

Volumn 24, Issue 5, 2000, Pages 329-336

  Bytautas, Laimutis ^a,b,c   Klein, Douglas J ^a   Schmalz, Thomas G ^a  

^a TEXAS A AND M UNIVERSITY AT GALVESTON   (United States)

^b VILNIUS UNIVERSITY   (Lithuania)

^c IOWA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACYCLIC HYDROCARBON SUBSTITUENT;

ARTICLE; CHEMICAL BINDING; CHEMICAL INTERACTION; CHEMICAL STRUCTURE; ISOMER; MOLECULAR DYNAMICS; PRIORITY JOURNAL;

EID: 0034038130     PISSN: 11440546     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906939i     Document Type: Article

References (58)

1. 1 Z. Slanina, Contemporary Theory of Chemical Isomerism, D. Reidel Pub., Dordrecht, 1986, ch. 2.
2. 2 A. von Humboldt, Versuche uber die gereizte Muskel- und Nervenfaser, nebst Vermutungen uber den chemischem Prozess in der Tier- und Pflanzenwelt, Berlin, 1797. A nice discussion of this work, including reproductions of the relevant text, appear in A. Kerber, MatCh, 1999, 39, 127. Most histories as in ref. 1 overlook Humboldt and instead begin with J. J. Berzelius (Ann. Phys. Chem., 1830, 19, 305), who introduced the word isomer.
3. 2 A. von Humboldt, Versuche uber die gereizte Muskel- und Nervenfaser, nebst Vermutungen uber den chemischem Prozess in der Tier- und Pflanzenwelt, Berlin, 1797. A nice discussion of this work, including reproductions of the relevant text, appear in A. Kerber, MatCh, 1999, 39, 127. Most histories as in ref. 1 overlook Humboldt and instead begin with J. J. Berzelius (Ann. Phys. Chem., 1830, 19, 305), who introduced the word isomer.
4. 2 A. von Humboldt, Versuche uber die gereizte Muskel- und Nervenfaser, nebst Vermutungen uber den chemischem Prozess in der Tier- und Pflanzenwelt, Berlin, 1797. A nice discussion of this work, including reproductions of the relevant text, appear in A. Kerber, MatCh, 1999, 39, 127. Most histories as in ref. 1 overlook Humboldt and instead begin with J. J. Berzelius (Ann. Phys. Chem., 1830, 19, 305), who introduced the word isomer.
5. 3 C. Brown, Trans. R. Soc. Edinburgh, 1864, 23, 707.
6. 4 (a) A. Cayley, Philos. Mag., 1874, 47, 444;
7. (b) A. Cayley, Rep. Br. Assn. Adv. Sci., 1887, 257.
8. 5 H. R. Henze and C. M. Blair, J. Am. Chem. Soc., 1931, 53, 3042 and 3077; C. M. Blair and H. R. Henze, J. Am. Chem. Soc., 1932, 54, 1098 and 1538.
9. 5 H. R. Henze and C. M. Blair, J. Am. Chem. Soc., 1931, 53, 3042 and 3077; C. M. Blair and H. R. Henze, J. Am. Chem. Soc., 1932, 54, 1098 and 1538.
10. 6 (a) G. Polya, Acta Math., 1937, 68, 145;
11. (b) G. Polya, Z. Kristallogr., Sect. A, 1936, 93, 414;
12. (c) G. Polya, Vierteljschr. Naturforsch. Ges. (Zurich), 1936, 81, 243.
13. 7 G. Polya and R. C. Read, Combinatorial Enumeration of Groups, Graphs, and Chemical Compounds, Springer-Verlag, Berlin, 1987.
14. 8 S. Fujita, Symmetry and Combinatorial Enumeration in Chemistry, Springer-Verlag, Berlin, 1991.
15. 9 N. Trinajstic̀, S. Nikolic̀, J. V. Knop, W. R. Muller and K. Szymanski, Computational Chemical Graph Theory: Characterization, Enumeration, and Generation of Chemical Structures by Computer Methods, Horwood/Simon & Schuster, New York, 1991.
16. 10 F. Harary and E. Palmer, Graphical Enumeration, Academic Press, New York, 1973.
17. 11 K. Balasubramanian, Chem. Rev., 1985, 85, 599.
18. 12 (a) L. Bytautas and D. J. Klein, J. Chem. Inf. Comput. Sci., 1998, 38, 1063;
19. (b) L. Bytautas and D. J. Klein, J. Chem. Inf. Comput. Sci., 1999, 39, 803.
20. 13 L. Bytautas and D. J. Klein, Croat. Chem. Acta, in press.
21. 14 L. Bytautas and D. Klein, Phys. Chem. Chem. Phys., 1999, 1, 5565.
22. 15 M. Randic and N. Trinajstic̀, Croat. Chem. Acta, 1987, 67, 1.
23. 16 R. C. Read, in Graph Theory and Applications, ed. Y. Alavi, D. R. Lick and A. T. White, Springer-Verlag, Berlin, 1972, pp. 243-259; R. C. Read, in Chemical Applications of Graph Theory, ed. A. T. Balaban, Academic Press, New York, 1976, pp. 25-61.
24. 16 R. C. Read, in Graph Theory and Applications, ed. Y. Alavi, D. R. Lick and A. T. White, Springer-Verlag, Berlin, 1972, pp. 243-259; R. C. Read, in Chemical Applications of Graph Theory, ed. A. T. Balaban, Academic Press, New York, 1976, pp. 25-61.
25. 17 (a) J.-R. Dias, Acc. Chem. Res., 1985, 18, 241;
26. (b) J.-R. Dias, J. Math. Chem., 1990, 4, 17;
27. (c) J.-R. Dias, Polycycl. Arom. Compd., 1994, 4, 87.
28. 18 (a) E. A. Smolenskii, Russ. J. Phys. Chem. (Engl. Transl.), 1964, 35, 700;
29. (b) M. Gordon and J. W. Kennedy, J. Chem. Soc., Faraday Trans. 2, 1973, 69, 484.
30. 19 (a) J. W. Essam, M. Gordon, J. W. Kennedy and P. Whittle, J. Chem. Soc., Faraday Trans. 2, 1977, 73, 1289;
31. (b) J. W. Kennedy and M. Gordon, Ann. N. Y. Acad. Sci., 1979, 319, 331.
32. 20 D. J. Klein, Int. J. Quantum Chem., Symp., 1986, 20, 153.
33. 21 (a) M. I. Skvortsova, I. I. Baskin, O. L. Slovokhotova and N. S. Zefirov, Dokl. Chem. (Engl. Transl.), 1994, 336, 496;
34. (b) I. I. Baskin, M. I. Skvortsova, I. V. Stankevich and N. S. Zefirov, Dokl. Chem.(Engl. Transl), 1994, 359, 346;
35. (c) W. Hässelbarth, MatCh, 1994, 31, 7.
36. 22 H. Kopp, Poggendorff's Ann. Phys., 1855, 96, 153 and 303.
37. 23 S. Smiles, The Relations between Chemical Constitution and some Physical Properties, Longman, Green & Co., London, 1910.
38. 24 Handbook of Chemical Property Estimation Methods, ed. W. J. Lyman, W. F. Reehl and D. H. Rosenblatt, McGraw-Hill, New York, 1982.
39. 25 V. M. Tatevskii, V. A. Benderskii and S. S. Yarovoi, Rules and Methods for Calculating the Physico-Chemical Properties of Paraffinic Hydrocarbons (Engl. Transl.), Pergamon Press, Oxford, 1961; J. D. Cox and G. Pilcher, Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970; S. W. Benson, Thermochemical Kinetics, John Wiley & Sons, New York, 1976.
40. 25 V. M. Tatevskii, V. A. Benderskii and S. S. Yarovoi, Rules and Methods for Calculating the Physico-Chemical Properties of Paraffinic Hydrocarbons (Engl. Transl.), Pergamon Press, Oxford, 1961; J. D. Cox and G. Pilcher, Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970; S. W. Benson, Thermochemical Kinetics, John Wiley & Sons, New York, 1976.
41. 25 V. M. Tatevskii, V. A. Benderskii and S. S. Yarovoi, Rules and Methods for Calculating the Physico-Chemical Properties of Paraffinic Hydrocarbons (Engl. Transl.), Pergamon Press, Oxford, 1961; J. D. Cox and G. Pilcher, Thermochemistry of Organic and Organometallic Compounds, Academic Press, New York, 1970; S. W. Benson, Thermochemical Kinetics, John Wiley & Sons, New York, 1976.
42. 26 N. Cohen and S. W. Benson, Chem. Rev., 1993, 93, 2419.
43. 27 (a) A. I. Vogel, J. Chem. Soc., 1948, 1833;
44. (b) A. I. Vogel, W. T. Cresswell, G. H. Jeffery and J. Leicester, J. Chem. Soc., 1952, 514.
45. 28 T. G. Schmalz, D. J. Klein and B. L. Sandleback, J. Chem. Inf. Comput. Sci., 1992, 32, 54.
46. 29 K. Ruud, H. Skaane, T. Helgaker, K. L. Bak and P. Jorgensen, J. Am. Chem. Soc., 1994, 116, 10135.
47. 30 C. Barter, R. G. Meisenheimer and D. P. Stevenson, J. Phys. Chem., 1960, 64, 1312.
48. 31 J. G. Oldenziel and N. J. Trappeniers, Physica A, 1976, 82, 565 and 581.
49. 32 P. Pascal, Ann. Chim. Phys., 1910, 19, 5.
50. 33 M. C. McHughes and R. D. Poshusta, J. Math. Chem., 1990, 4, 227.
51. 34 (a) D. J. Klein, J. Chem. Phys., 1981, 75, 5186;
52. (b) P. G. de Gennes, J. Phys. Lett., 1983, 44, 351;
53. (c) G. R. Newkome, V. K. Gupta, G. R. Baker and Z.-Q. Yao, J. Org. Chem., 1985, 50, 2003.
54. 35 See, for example, any issue of J. Comb. Chem., or M. A. Gallop, R. W. Barrett, W. J. Dower, S. P. A. Fodor and E. M. Gordon, J. Med. Chem., 1994, 37, 1233; R. N. Zuckermann, E. J. Martin, D. C. Spellmeyer, G. B. Stauber, K. R. Shoemaker, J. M. Kerr, B. M. Figliozzi, D. A. Goff, M. A. Siani, R. J. Simon, S. C. Banville, E. G. Brown, L. Wang, L. S. Richter and W. H. Moos, J. Med. Chem., 1994, 37, 2678; Combinatorial Chemistry, ed. A. W. Czarnik and S. H. DeWitt, American Chemical Society, Washington, DC, 1997.
55. 35 See, for example, any issue of J. Comb. Chem., or M. A. Gallop, R. W. Barrett, W. J. Dower, S. P. A. Fodor and E. M. Gordon, J. Med. Chem., 1994, 37, 1233; R. N. Zuckermann, E. J. Martin, D. C. Spellmeyer, G. B. Stauber, K. R. Shoemaker, J. M. Kerr, B. M. Figliozzi, D. A. Goff, M. A. Siani, R. J. Simon, S. C. Banville, E. G. Brown, L. Wang, L. S. Richter and W. H. Moos, J. Med. Chem., 1994, 37, 2678; Combinatorial Chemistry, ed. A. W. Czarnik and S. H. DeWitt, American Chemical Society, Washington, DC, 1997.
56. 35 See, for example, any issue of J. Comb. Chem., or M. A. Gallop, R. W. Barrett, W. J. Dower, S. P. A. Fodor and E. M. Gordon, J. Med. Chem., 1994, 37, 1233; R. N. Zuckermann, E. J. Martin, D. C. Spellmeyer, G. B. Stauber, K. R. Shoemaker, J. M. Kerr, B. M. Figliozzi, D. A. Goff, M. A. Siani, R. J. Simon, S. C. Banville, E. G. Brown, L. Wang, L. S. Richter and W. H. Moos, J. Med. Chem., 1994, 37, 2678; Combinatorial Chemistry, ed. A. W. Czarnik and S. H. DeWitt, American Chemical Society, Washington, DC, 1997.
57. 36 See, for example, G. Grassy, B. Calas, A. Yasri, R. Lahana, J. Woo, S. Iyer, M. Kaczorek, R. Floc'h and R. Buelow, Nature Biotech., 1998, 16, 748; L. Xue, J. W. Godden and J. Bajorath, J. Chem. Inf. Comput. Sci., 1999, 39, 881.
58. 36 See, for example, G. Grassy, B. Calas, A. Yasri, R. Lahana, J. Woo, S. Iyer, M. Kaczorek, R. Floc'h and R. Buelow, Nature Biotech., 1998, 16, 748; L. Xue, J. W. Godden and J. Bajorath, J. Chem. Inf. Comput. Sci., 1999, 39, 881.