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Molecular topology and chemical reactivity of polynuclear benzenoid hydrocarbons

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Advances in the Theory of Benzenoid Hydrocarbons

Part of the book series: Topics in Current Chemistry ((TOPCURRCHEM,volume 153))

Abstract

After a brief discussion of the notion of molecular topology and the analogy principle as related to topology/reactivity relationships more recent developments in the field of reactivity indices for polynuclear benzenoid hydrocarbons are reviewed. Reaction mechanisms and correlations of reactivity indices with rates of electrophilic substitution and Diels-Alder reactions, thermally induced polymerization, and biochemical transformations of benzenoid hydrocarbons are discussed.

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7 References

  1. Woolley RG (1978) J. Am. Chem. Soc. 100: 1073

    Google Scholar 

  2. Claverie P, Diner S (1980) Israel J. Chem. 19: 54

    Google Scholar 

  3. Zander M, Polansky OE (1984) Naturwiss. 71: 623

    Google Scholar 

  4. Gutman I, Polansky OE (1986) Mathematical concepts in organic chemistry, Springer, Berlin Heidelberg New York

    Google Scholar 

  5. Merrifield RE, Simmons HE (1983) In: King RB (ed) Chemical applications of topology and graph theory, Elsevier, Amsterdam; pp. 1–16; (1980) Theor. Chim. Acta 55: 55

    Google Scholar 

  6. Polansky OE (1986) Z. Naturforsch. 41a: 560

    Google Scholar 

  7. Ruedenberg K, Scherr CW (1953) J. Chem. Phys. 21: 1565

    Google Scholar 

  8. Hiberty PC, Shaik, SS, Lefour J-M, Ohanessian G (1985) J. Org. Chem. 50: 4657

    Google Scholar 

  9. Graovac A, Gutman I, Trinajstic N (1977) Topological approach to the chemistry of conjugated molecules, Springer, Berlin Heidelberg New York (Lecture Notes in Chemistry No. 4)

    Google Scholar 

  10. Zander M (1986) Match 19: 171

    Google Scholar 

  11. Clar E (1964) Polycyclic hydrocarbons, Academic, New York vol 1, pp 41–69

    Google Scholar 

  12. Balaban AT, Biermann D, Schmidt W (1985) Noveau J. Chim. 9: 443

    Google Scholar 

  13. Kekulé A (1861) Lehrbuch der Organischen Chemie, Band 1, Verlag von Ferdinand Enke, Erlangen, pp 124–132

    Google Scholar 

  14. Hammett LP (1940) Physical organic chemistry, McGraw-Hill, New York p 348

    Google Scholar 

  15. Wold S, Sjöström M (1978) In: Chapman NB, Shorter J (eds) Correlation analysis in chemistry, Plenum, New York, chapt 1

    Google Scholar 

  16. Dewar MJS, Dougherty RC (1975) The PMO theory of organic chemistry, Plenm, New York

    Google Scholar 

  17. Klumpp GW (1978) Reaktivität in der Organischen Chemie, Thieme, Stuttgart vol 2, pp 367–369

    Google Scholar 

  18. Terminology according to Harary F (1974) Graphentheorie, R. Oldenbourg, Munich

    Google Scholar 

  19. Zander M (1985) Z. Naturforsch. 40 a: 636

    Google Scholar 

  20. Clar E (1972) The aromatic sextet, Wiley, London

    Google Scholar 

  21. Zander M (1982) Naturwissenschaften 69: 436

    Google Scholar 

  22. Balaban AT, Harary F (1968) Tetrahedron 24: 2505

    Google Scholar 

  23. Streitwieser A Jr (1961) Molecular orbital theory for organic chemists, Wiley, New York

    Google Scholar 

  24. Herndon WC (1975) J. Org. Chem. 40: 3583

    Google Scholar 

  25. Herndon WC (1980) Israel J. Chem. 20: 270

    Google Scholar 

  26. Herndon WC (1973) Tetrahedron 29: 3

    Google Scholar 

  27. Herndon WC (1974) J. Chem. Educ. 51: 10

    Google Scholar 

  28. Longuet-Higgins HC (1950) J. Chem. Phys. 18: 265, 275, 283

    Google Scholar 

  29. Biermann D, Schmidt W (1980) Israel J. Chem. 20: 312

    Google Scholar 

  30. Herndon WC (1982) Tetrahedron 38: 1389

    Google Scholar 

  31. Brown RL (1983) J. Comput. Chem. 4: 556

    Google Scholar 

  32. v Szentpaly L (1981) J. Photochem. 17: 112

    Google Scholar 

  33. v Szentpaly L, Herndon WC (1988) In: Ebert LB (ed) Polynuclear aromatic compounds, American Chemical Society, Washington DC, Chapt 17 (Advances in Chemistry Series 217)

    Google Scholar 

  34. Kuhn H (1948) Helv. Chim. Acta 31: 1441; (1949) Helv. Chim. Acta 32: 2247

    Google Scholar 

  35. v Szentpaly L (1981) Chem. Phys. Lett. 77: 352

    Google Scholar 

  36. Polansky OE, Derflinger G (1967) Int. J. Quantum Chem. 1: 379

    Google Scholar 

  37. Mehlhorn A, Fratev F, Polansky OE, Monev V (1984) Match 15: 3

    Google Scholar 

  38. Sofer H, Derflinger G, Polansky OE (1968) Mh. Chem. 99: 1879; 1895

    Google Scholar 

  39. Zander M (1979) Z. Naturforsch. 34a: 521

    Google Scholar 

  40. Golebiewski A (1974) Acta Phys. Polonica A46: 719

    Google Scholar 

  41. Fratev F, Polansky OE, Mehlhorn A, Monev V (1979) J. Mol. Struct. 56: 245

    Google Scholar 

  42. Hess BA Jr, Schaad LJ (1971) J. Am. Chem. Soc. 93: 305

    Google Scholar 

  43. Schaad LJ, Hess BA Jr (1974) J. Chem. Educ. 51: 640

    Google Scholar 

  44. Herndon WC (1981) J. Org. Chem. 46: 2119

    Google Scholar 

  45. Hess BA Jr, Schaad LJ, Herndon WC, Biermann D, Schmidt W (1981) Tetrahedron 37: 2983

    Google Scholar 

  46. Léger A, d'Hendecourt L, Boccara N (eds) (1987) Polycyclic aromatic hydrocarbons and astrophysics, D. Reidel, Dordrecht

    Google Scholar 

  47. Stein SE, Brown RL (1985) Carbon 23: 105

    Google Scholar 

  48. Stein SE, Brown RL (1987) Mol. Struct. Energ. 2: 37

    Google Scholar 

  49. Pryor WA, Gleicher GJ, Cosgrove JP, Church DF (1984) J. Org. Chem. 49: 5189

    Google Scholar 

  50. Marsh J (1977) Advanced Organic Chemistry, McGraw Hill, New York

    Google Scholar 

  51. Baker R, Eaborn C, Taylor R: J. Chem. Soc. Perkin II 1972: 97

    Google Scholar 

  52. Krygowski TM (1972) Tetrahedron 28: 4981

    Google Scholar 

  53. Aue DH, Bowers MT (1979) In: Bowers MT (ed) Gas-phase ion chemistry, Academic, New York Chapt 9

    Google Scholar 

  54. Meot-Ner (Mautner) M (1980) J. Phys. Chem. 84: 2716

    Google Scholar 

  55. Altschuler L, Berliner E (1966) J. Am. Chem. Soc. 88: 5837

    Google Scholar 

  56. Streitwieser A Jr, Mowery PC, Jesaitis RG, Lewis A (1970) J. Am. Chem. Soc. 92: 6529

    Google Scholar 

  57. Streitwieser A Jr, (1960) J. Am. Chem. Soc. 82: 4123

    Google Scholar 

  58. v Szentpaly L, Herndon WC (1984) Croatica Chemica Acta 57: 1621

    Google Scholar 

  59. Shawali AS, Hassaneen HM, Párkányi C, Herndon WC (1983) J. Org. Chem. 48: 4800

    Google Scholar 

  60. Archer WJ, Shafig YE, Taylor RJ (1981) J. Chem. Soc. Perkin Trans. 2: 675

    Google Scholar 

  61. Clar E (1931) Ber. Dtsch. Chem. Ges. 64: 1682

    Google Scholar 

  62. Diels O, Alder K (1931) Justus Liebigs Ann. Chem. 486: 191

    Google Scholar 

  63. Biermann D, Schmidt W (1980) J. Am. Chem. Soc. 102: 3163

    Google Scholar 

  64. Biermann D, Schmidt W (1980) J. Am. Chem. Soc. 102: 3173

    Google Scholar 

  65. Franck HG, Zander M (1966) Chem. Ber. 99: 1272

    Google Scholar 

  66. Blümer G-P, Gundermann K-D, Zander M (1976) Chem. Ber. 109: 1991

    Google Scholar 

  67. Fukui K (1970) Fortschr. Chem. Forsch. 15: 1; Houk KN (1975) Acc. Chem. Res. 8: 361

    Google Scholar 

  68. Dewar MJS (1984) J. Am. Chem. Soc. 106: 209

    Google Scholar 

  69. Zander M (1965) Angew. Chem. Intern. Ed. Engl. 4: 930

    Google Scholar 

  70. Siebrand W (1966) J. Chem. Phys. 44: 4055

    Google Scholar 

  71. Bartle KD, Jones DW (1972) Adv. Org. Chem. 8: 317

    Google Scholar 

  72. Clar E (1932) Ber. Dtsch. Chem. Ges. 65: 846

    Google Scholar 

  73. Clar E, Zander M: J. Chem. Soc. 1957: 4616; Zander M (1960) Angew. Chem. 72: 513

    Google Scholar 

  74. Zander M (1969) Justus Liebigs Ann. Chem. 723: 27

    Google Scholar 

  75. Zander M (1978) Z. Naturforsch. 33a: 1395

    Google Scholar 

  76. Biermann D (1981) Thesis, Ludwig-Maximilians-University, Munich

    Google Scholar 

  77. Clar E, Zander M: J. Chem. Soc. 1958: 1861

    Google Scholar 

  78. Lewis IC, Singer LS (1988) In Ebert LB (ed) Polynuclear Aromatic Compounds, American Chemical Society, Washington DC, Chapt 16 (Advances in Chemistry Series 217)

    Google Scholar 

  79. Lewis IC (1982) Carbon 20: 519

    Google Scholar 

  80. Zander M, Haase J, Dreeskamp H (1982) Erdöl und Kohle · Erdgas · Petrochem. 35: 65

    Google Scholar 

  81. Lewis IC (1980) Carbon 18: 191

    Google Scholar 

  82. Stein SE (1981) Carbon 19: 421

    Google Scholar 

  83. Stein SE, Griffith LL, Billmers R, Chen RH (1987) J. Org. Chem. 52: 1582

    Google Scholar 

  84. Lewis IC, Edstrom T (1963) J. Org. Chem. 28: 2050

    Google Scholar 

  85. Yokono T, Miyazawa K, Sanada Y, Marsh H (1979) Fuel 58: 692

    Google Scholar 

  86. Zander M (1986) Fuel 65: 1019

    Google Scholar 

  87. IARC Monographs (International Agency for Research on Cancer), vol 3, Lyon 1973

    Google Scholar 

  88. Iball I (1939) Am. J. Cancer 35: 188

    Google Scholar 

  89. Herndon WC: Private Communication cited in

    Google Scholar 

  90. Popp FA (1976) In: Deutsch F (ed) Molecular basis of malignancy, Georg Thieme, Stuttgart, pp 47–55

    Google Scholar 

  91. For a review see Zander M (1980) In: Hutzinger O (ed) Anthropogenic compounds, Springer, Berlin Heidelberg New York pp 109–131 (Handbook of environmental chemistry vol 3, Part A)

    Google Scholar 

  92. Oesch F (1973) Xenobiotica 3: 305

    Google Scholar 

  93. Buening MK (1978) Proc. Nat. Acad. Sci. USA 75: 5358

    Google Scholar 

  94. Jerina DM et al. (1976) In: de Serres FJ et al. (eds) In: In vitro metabolic activation in mutagenesis testing, Elsevier/North Holland, Amsterdam, pp 159–177

    Google Scholar 

  95. Qianhuan D (1980) Scientia Sinica 23: 453

    Google Scholar 

  96. v Szentpaly L (1984) J. Am. Chem. Soc. 106: 6021

    Google Scholar 

  97. Herndon WC (1974) Int. J. Quantum Chem., Quantum Biol. Symp. 1: 123

    Google Scholar 

  98. Polansky OE, Zander M (1982) J. Mol Struct. 84: 361

    Google Scholar 

  99. Motoc I, Polansky OE (1984) Z. Naturforsch. 39a: 1053

    Google Scholar 

  100. Polansky OE, Mark G, Zander M (1987) Der topologische Effekt an Molekülorbitalen (TEMO), Schriftenreihe des Max-Planck-Instituts für Strahlenchemie No. 31, Mülheim an der Ruhr (FRG)

    Google Scholar 

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  1. Rütgerswerke AG, D-4620, Castrop-Rauxel, FRG

    Maximilian Zander

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  1. Maximilian Zander
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Ivan Gutman Sven J. Cyvin

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© 1990 Springer-Verlag

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Zander, M. (1990). Molecular topology and chemical reactivity of polynuclear benzenoid hydrocarbons. In: Gutman, I., Cyvin, S.J. (eds) Advances in the Theory of Benzenoid Hydrocarbons. Topics in Current Chemistry, vol 153. Springer, Berlin, Heidelberg. https://doi.org/10.1007/3-540-51505-4_20

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  • DOI: https://doi.org/10.1007/3-540-51505-4_20

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  • Print ISBN: 978-3-540-51505-0

  • Online ISBN: 978-3-540-48185-0

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