Fully-Naphthalenoid Hydrocarbons and their Conjugation Modes

Abstract A fully-naphthalenoid hydrocarbon (FUN) is a benzenoid hydrocarbon whose all π-electrons can be (formally) grouped into disjoint naphthalene-units. The cyclic conjugation in FUNs is studied by means of the energy-effects of their various cycles. It is found that the dominant conjugation modes in FUNs are those involving the 6- and 10-membered cycles of the “full” naphthalene fragments. The cycles belonging to the “empty” domains of a FUN have significantly smaller energy-effects.

[1]  H. Hosoya,et al.  Mo- and Vb-benzene characters : Analysis of the “clar's aromatic sextet” in polycyclic aromatic hydrocarbons , 1980 .

[2]  I. Gutman,et al.  Cyclic Conjugation in Peropyrenes , 1991 .

[3]  On the Number of Aromatic Sextets in a Benzenoid Hydrocarbon , 1976 .

[4]  G. Habermehl,et al.  ReviewPure appl. Chem: Rinehart, K. L., et al. Marine natural products as sources of antiviral, antimicrobial, and antineoplastic Agents. 53, 795 (1981). (K. L. Rinehart, University of Illinois, Urbana, IL 61801, U.S.A.) , 1983 .

[5]  E. Clar,et al.  378. 1 : 12-2 : 3-10 : 11-Tribenzoperylene , 1958 .

[6]  I. Gutman,et al.  Mathematical Concepts in Organic Chemistry , 1986 .

[7]  E. Clar.  The aromatic sextet , 1972 .

[8]  O. Polansky,et al.  Zur Clar'schen Theorie Lokaler Benzoider Gebiete in Kondensierten Aromaten , 1967 .

[9]  M. Randic.  On the characterization of local aromatic properties in benzenoid hydrocarbons , 1974 .

[10]  S. J. Cyvin,et al.  Introduction to the theory of benzenoid hydrocarbons , 1989 .

[11]  I. Gutman,et al.  Quantitative approach to hückel rule the relations between the cycles of a molecular graph and the thermodynamic stability of a conjugated molecule , 1977 .

[12]  Ivan Gutman,et al.  Cyclic conjugation and the hückel molecular orbital model , 1981 .

[13]  Nonaromatic benzenoid hydrocarbons , 1990 .

[14]  I. Gutman,et al.  Characterization of all-benzenoid hydrocarbons , 1991 .

[15]  M. L. Ellzey,et al.  Resonance theory. V. Resonance energies of benzenoid and nonbenzenoid .pi. systems , 1974 .