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
Woolley RG (1978) J. Am. Chem. Soc. 100: 1073
Claverie P, Diner S (1980) Israel J. Chem. 19: 54
Zander M, Polansky OE (1984) Naturwiss. 71: 623
Gutman I, Polansky OE (1986) Mathematical concepts in organic chemistry, Springer, Berlin Heidelberg New York
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
Polansky OE (1986) Z. Naturforsch. 41a: 560
Ruedenberg K, Scherr CW (1953) J. Chem. Phys. 21: 1565
Hiberty PC, Shaik, SS, Lefour J-M, Ohanessian G (1985) J. Org. Chem. 50: 4657
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)
Zander M (1986) Match 19: 171
Clar E (1964) Polycyclic hydrocarbons, Academic, New York vol 1, pp 41–69
Balaban AT, Biermann D, Schmidt W (1985) Noveau J. Chim. 9: 443
Kekulé A (1861) Lehrbuch der Organischen Chemie, Band 1, Verlag von Ferdinand Enke, Erlangen, pp 124–132
Hammett LP (1940) Physical organic chemistry, McGraw-Hill, New York p 348
Wold S, Sjöström M (1978) In: Chapman NB, Shorter J (eds) Correlation analysis in chemistry, Plenum, New York, chapt 1
Dewar MJS, Dougherty RC (1975) The PMO theory of organic chemistry, Plenm, New York
Klumpp GW (1978) Reaktivität in der Organischen Chemie, Thieme, Stuttgart vol 2, pp 367–369
Terminology according to Harary F (1974) Graphentheorie, R. Oldenbourg, Munich
Zander M (1985) Z. Naturforsch. 40 a: 636
Clar E (1972) The aromatic sextet, Wiley, London
Zander M (1982) Naturwissenschaften 69: 436
Balaban AT, Harary F (1968) Tetrahedron 24: 2505
Streitwieser A Jr (1961) Molecular orbital theory for organic chemists, Wiley, New York
Herndon WC (1975) J. Org. Chem. 40: 3583
Herndon WC (1980) Israel J. Chem. 20: 270
Herndon WC (1973) Tetrahedron 29: 3
Herndon WC (1974) J. Chem. Educ. 51: 10
Longuet-Higgins HC (1950) J. Chem. Phys. 18: 265, 275, 283
Biermann D, Schmidt W (1980) Israel J. Chem. 20: 312
Herndon WC (1982) Tetrahedron 38: 1389
Brown RL (1983) J. Comput. Chem. 4: 556
v Szentpaly L (1981) J. Photochem. 17: 112
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)
Kuhn H (1948) Helv. Chim. Acta 31: 1441; (1949) Helv. Chim. Acta 32: 2247
v Szentpaly L (1981) Chem. Phys. Lett. 77: 352
Polansky OE, Derflinger G (1967) Int. J. Quantum Chem. 1: 379
Mehlhorn A, Fratev F, Polansky OE, Monev V (1984) Match 15: 3
Sofer H, Derflinger G, Polansky OE (1968) Mh. Chem. 99: 1879; 1895
Zander M (1979) Z. Naturforsch. 34a: 521
Golebiewski A (1974) Acta Phys. Polonica A46: 719
Fratev F, Polansky OE, Mehlhorn A, Monev V (1979) J. Mol. Struct. 56: 245
Hess BA Jr, Schaad LJ (1971) J. Am. Chem. Soc. 93: 305
Schaad LJ, Hess BA Jr (1974) J. Chem. Educ. 51: 640
Herndon WC (1981) J. Org. Chem. 46: 2119
Hess BA Jr, Schaad LJ, Herndon WC, Biermann D, Schmidt W (1981) Tetrahedron 37: 2983
Léger A, d'Hendecourt L, Boccara N (eds) (1987) Polycyclic aromatic hydrocarbons and astrophysics, D. Reidel, Dordrecht
Stein SE, Brown RL (1985) Carbon 23: 105
Stein SE, Brown RL (1987) Mol. Struct. Energ. 2: 37
Pryor WA, Gleicher GJ, Cosgrove JP, Church DF (1984) J. Org. Chem. 49: 5189
Marsh J (1977) Advanced Organic Chemistry, McGraw Hill, New York
Baker R, Eaborn C, Taylor R: J. Chem. Soc. Perkin II 1972: 97
Krygowski TM (1972) Tetrahedron 28: 4981
Aue DH, Bowers MT (1979) In: Bowers MT (ed) Gas-phase ion chemistry, Academic, New York Chapt 9
Meot-Ner (Mautner) M (1980) J. Phys. Chem. 84: 2716
Altschuler L, Berliner E (1966) J. Am. Chem. Soc. 88: 5837
Streitwieser A Jr, Mowery PC, Jesaitis RG, Lewis A (1970) J. Am. Chem. Soc. 92: 6529
Streitwieser A Jr, (1960) J. Am. Chem. Soc. 82: 4123
v Szentpaly L, Herndon WC (1984) Croatica Chemica Acta 57: 1621
Shawali AS, Hassaneen HM, Párkányi C, Herndon WC (1983) J. Org. Chem. 48: 4800
Archer WJ, Shafig YE, Taylor RJ (1981) J. Chem. Soc. Perkin Trans. 2: 675
Clar E (1931) Ber. Dtsch. Chem. Ges. 64: 1682
Diels O, Alder K (1931) Justus Liebigs Ann. Chem. 486: 191
Biermann D, Schmidt W (1980) J. Am. Chem. Soc. 102: 3163
Biermann D, Schmidt W (1980) J. Am. Chem. Soc. 102: 3173
Franck HG, Zander M (1966) Chem. Ber. 99: 1272
Blümer G-P, Gundermann K-D, Zander M (1976) Chem. Ber. 109: 1991
Fukui K (1970) Fortschr. Chem. Forsch. 15: 1; Houk KN (1975) Acc. Chem. Res. 8: 361
Dewar MJS (1984) J. Am. Chem. Soc. 106: 209
Zander M (1965) Angew. Chem. Intern. Ed. Engl. 4: 930
Siebrand W (1966) J. Chem. Phys. 44: 4055
Bartle KD, Jones DW (1972) Adv. Org. Chem. 8: 317
Clar E (1932) Ber. Dtsch. Chem. Ges. 65: 846
Clar E, Zander M: J. Chem. Soc. 1957: 4616; Zander M (1960) Angew. Chem. 72: 513
Zander M (1969) Justus Liebigs Ann. Chem. 723: 27
Zander M (1978) Z. Naturforsch. 33a: 1395
Biermann D (1981) Thesis, Ludwig-Maximilians-University, Munich
Clar E, Zander M: J. Chem. Soc. 1958: 1861
Lewis IC, Singer LS (1988) In Ebert LB (ed) Polynuclear Aromatic Compounds, American Chemical Society, Washington DC, Chapt 16 (Advances in Chemistry Series 217)
Lewis IC (1982) Carbon 20: 519
Zander M, Haase J, Dreeskamp H (1982) Erdöl und Kohle · Erdgas · Petrochem. 35: 65
Lewis IC (1980) Carbon 18: 191
Stein SE (1981) Carbon 19: 421
Stein SE, Griffith LL, Billmers R, Chen RH (1987) J. Org. Chem. 52: 1582
Lewis IC, Edstrom T (1963) J. Org. Chem. 28: 2050
Yokono T, Miyazawa K, Sanada Y, Marsh H (1979) Fuel 58: 692
Zander M (1986) Fuel 65: 1019
IARC Monographs (International Agency for Research on Cancer), vol 3, Lyon 1973
Iball I (1939) Am. J. Cancer 35: 188
Herndon WC: Private Communication cited in
Popp FA (1976) In: Deutsch F (ed) Molecular basis of malignancy, Georg Thieme, Stuttgart, pp 47–55
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)
Oesch F (1973) Xenobiotica 3: 305
Buening MK (1978) Proc. Nat. Acad. Sci. USA 75: 5358
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
Qianhuan D (1980) Scientia Sinica 23: 453
v Szentpaly L (1984) J. Am. Chem. Soc. 106: 6021
Herndon WC (1974) Int. J. Quantum Chem., Quantum Biol. Symp. 1: 123
Polansky OE, Zander M (1982) J. Mol Struct. 84: 361
Motoc I, Polansky OE (1984) Z. Naturforsch. 39a: 1053
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)
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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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