Partitioning of π-electrons in rings of polycyclic conjugated hydrocarbons. 5. nonalternant compounds

Journal of Chemical Information and Computer Sciences

Volumn 44, Issue 5, 2004, Pages 1701-1707

  Balaban, Alexandru T ^a   Randić, Milan ^b,c  

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

^b NATIONAL INSTITUTE OF CHEMISTRY   (Slovenia)

^c NONE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BONDING ORBITALS; CATACONDENSATION; CORONA CONDENSATION;

ANNEALING; CHEMICAL BONDS; CONDENSATION; ELECTRON ENERGY LEVELS; ISOMERIZATION; MOLECULAR STRUCTURE; SUBSTITUTION REACTIONS;

POLYCYCLIC AROMATIC HYDROCARBONS;

EID: 5444260130     PISSN: 00952338     EISSN: None     Source Type: Journal    
DOI: 10.1021/ci049842y     Document Type: Article

References (47)

1. Balaban, A. T.; Randić, M. Partitioning of π-electrons in rings of polycyclic conjugated hydrocarbons. Part 1. Catacondensed benzenoids, Polycyclic Arom. Comput. 2004, in press.
2. Balaban, A. T.; Randić, M. Partitioning of π-electrons in rings of polycyclic conjugated hydrocarbons. Part 3. Perifusenes. New J. Chem. 2004, in press.
3. Balaban, A. T.; Randić, M. Partitioning of π-electrons in rings of polycyclic benzenoid hydrocarbons. Part 2. Coronoids. J. Chem. Inf. Comput. Sci. 2004, 44, 50-59.
4. Balaban, A. T. Chemical graphs. XVII. (Aromaticity, X). cata-Condensed polycyclic hydrocarbons which fulfill the Huckel rule but lack closed electronic shells. Rev. Roum. Chim. 1972, 17, 1531-1543.
5. Van Ornum, S. G.; Bruendl, M. M.; Cook, J. M. The Livinghouse catalytic approach to the tandem Pauson-Khand reaction. Entry into the parent ring systems of dicyclopenta[a,f]pentalene and dicyclopenta[a,e]pentalene. Tetrahedron Lett. 1998, 39, 6649-6650.
6. Van Ornum, S. G.; Cook, J. M. Generation of four five-membered rings in a one pot process. Studies directed toward the synthesis of dicyclopenta[a,d] pentalene via the tandem Pauson-Khand reaction. Tetrahedron Lett. 1996, 37, 7185-8188.
7. Van Ornum, S. G.; Cook, J. M. Formation of six carbon-carbon bonds in a one pot process. Generation of the dicyclopenta[a, e]pentalene ring system via the tandem Pauson-Khand reaction. Tetrahedron Lett. 1997, 38, 3657-3658.
8. Toyota, A.; Nakajima, T. Electronic structures of some cata-condensed nonalternant hydrocarbons: pentalenopentalenes, azulenoazulenes, and pentalenoazulenes. Tetrahedron 1991, 37, 2575-2579.
9. Toyota, A. Violation of Hund's rule in the lowest excited singlet-triplet pairs of dicyclohepta[cd,gh]pentalene and dicyclopenta[ef,kl]-heptalene.
10. Hess, B. A., Jr.; Schaad, L. J. Hückel molecular orbital resonance energies. The nonalternant hydrocarbons. J. Org. Chem. 1971, 36, 3418-3423.
11. Wilcox, C. F., Jr. Stability of molecules containing nonalternant rings. J. Am. Chem. Soc. 1969, 91, 2732-2736.
12. Zhou, Z.; Parr, R.G. New measures of aromaticity: absolute hardness and relative hardness. Angew. Chem., Int. Ed. Engl. 1968, 7, 80-7379.
13. Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Ya. Aromaticity and Antiaromaticity. Electronic and Structural Aspects; Wiley-Interscience: New York, 1994.
14. Lloyd, D. Nonbenzenoid Conjugated Carbocyclic Compounds', Elsevier: Amsterdam, 1984.
15. Non-Benzenoid Aromatic Compounds; Ginsburg, D., Ed.; Interscience: New York, 1959.
16. Warner, P. In Topics in Nonbenzenoid Aromatic Chemistry; Nozoe, T., Breslow, R., Hafner, K., Ito, S., Murata, I., Eds.; Horokawa Publishing Co.: Tokyo, 1977; Vol. 2, p 293.
17. Balaban, A. T.; Banciu, M.; Ciorba, V. Annulenes, Benzo-, Hetero-, Homo-Derivatives and Their Valence homers; CRC Press: Boca Raton, FL, 1986; three volumes.
18. Hafner, K. New aspects in fulvene chemistry: cyclic cross-conjugated 10-π-electron systems. In Aromaticity, Pseudoaromaticity, Antiaromaticity; Bergmann, E. D., Pullman, B., Eds.; The Israel Academy of Sciences and Humanities: Jerusalem, 1971; pp 256-268.
19. Hopf, H. Classics in Hydrocarbon Chemistry. Syntheses, Concepts, Perspectives; Wiley-VCH: Weinheim, 2000; pp 277-290.
20. Slayden, S. W., Liebman, J. F. The energetics of aromatic hydrocarbons: an experimental thermochemical perspective. Chem. Rev. 2001, 101, 1541-1566.
21. Randić, M. Aromaticity and conjugation. J. Am. Chem. Soc. 1977, 99, 444-450.
22. Randić, M. Algebraic Kekulé formulas for benzenoid hydrocarbons. J. Chem. Inf. Comput. Sci. 2004, 44, 365-372.
23. Gutman, I.; Vukičević, D.; Graovac, A.; Randić, M. Algebraic Kekulé structures for benzenoid hydrocarbons. J. Chem. Inf. Comput. Sci. 2004, 44, 296-299.
24. Randić, M. A graph theoretical approach to conjugation and resonance energies of hydrocarbons. Tetrahedron 1977, 33, 1905-1920.
25. Randić, M.; Plavsić, D. Trinajstić, N. Aromaticity in polycyclic conjugated hydrocarbon dianions. Theochem. 1989, 54, 249-274.
26. Randić, M. Aromaticity of polycyclic conjugated hydrocarbons. Chem. Rev. 2003, 103, 3449-3606.
27. 52. Hafner, K.; Süss, H. U. 1,3,5-Tri-tert-butylpentalene. A stabilized planar 8π-electron system. Angew. Chem., Int. Ed. Engl. 1973, 12, 575-577.
28. Paquette, L. A.; Browne, A. R.; Chamot, E. An expeditious synthesis of heptalene from naphthalene via a bis(bicyclo[1.1.0]butane) intermediate. Angew. Chem., Int. Ed. Engl. 1979, 18, 546-547.
29. Dauben, H. J., Jr.; Bertelli, A. Heptalene. J. Am. Chem. Soc. 1961, 83, 4659-4650.
30. Vogel, E.; Ippen, J. Stable heptalenes -3,8-dibromoheptalene. Angew. Chem., Int. Ed. Engl. 1974, 13, 734-735.
31. Bally, T.; Chai, S.; Neuenschwander, M.; Zhu, Z. Pentalene: formation, electronic, and vibrational structure. J. Am. Chem. Soc. 1997, 119, 1869-1875.
32. 60 and some related species. Chem. Phys. Lett. 1986, 128, 501-503.
33. Fowler, P. W.; Monolopoulos, D. E. An Atlas of Fullerenes; Clarendon Press: Oxford, 1995; pp 120-148.
34. 2]dicyclopenta[ef,kl]-heptalene (azupyrene) to pyrene. Erratum, J. Org. Chem. 1992, 57, 1318.
35. 2]dicyclopenta[ef,kl]-heptalene (azupyrene) to pyrene. Erratum, J. Org. Chem. 1992, 57, 1318.
36. 2]dicyclopenta[ef,kl]-heptalene (azupyrene) to pyrene. Erratum, J. Org. Chem. 1992, 57, 1318.
37. Balaban, A. T.; Schmalz, T. G.; Zhu, H.; Klein, D. J. Generalizations of the Stone-Wales rearrangement for cage compounds, including fullerenes. Theochem. 1996, 363, 291-301.
38. Oda, M.; Oikawa, H. The synthesis of bicyclo[6.2.0]decapentaene. Tetrahedron Lett. 1980, 21, 107-110. Kawka, D.; Mues, P.; Vogel, E. Octalene - bicyclo[6.2.0]decapentaene conversion mediated by transition-metal complexes. Angew. Chem., Int. Ed. Engl. 1983, 22, 1003-1004.
39. Oda, M.; Oikawa, H. The synthesis of bicyclo[6.2.0]decapentaene. Tetrahedron Lett. 1980, 21, 107-110. Kawka, D.; Mues, P.; Vogel, E. Octalene - bicyclo[6.2.0]decapentaene conversion mediated by transition-metal complexes. Angew. Chem., Int. Ed. Engl. 1983, 22, 1003-1004.
40. Havenith, R. W. A.; Lugli, F.; Fowler, P. W.; Steiner, E. Ring current patterns in annelated bicylic polyenes. J. Phys. Chem. A 2002, 106, 5703-5708.
41. Tai, J.; Allinger, N. L. Effect of inclusion of electron correlation in MM3 studies of cyclic conjugated compounds. J. Comput. Chem. 1998, 19, 475-487.
42. Balaban, A. T.; Oniciu, D.; Katritzky, A. R. Aromaticity as a cornerstone to heterocyclic chemistry. Chem. Rev. 2004, 104, 2777-2812.
43. Platt, J. R. The box model and electron densities in conjugated systems. J. Chem. Phys. 1954, 22, 1448-1455.
44. Bochvar, D. A.; Stankevich, I. V.; Tutkevich, A. V. Hückel's (4n + 2) rule, Izvest. Akad. Nauk SSSR, Otdel. Khim. Nauk 1969, 1185-1186.
45. Ivanciuc, O.; Bytautas, L.; Klein, D. J. Mean-field resonating-valence- bond theory for unpaired π-electrons in benzenoid carbon species, J. Chem. Phys. 2002, 116, 4735-4748. Ivanciuc, O.; Klein, D. J.; Bytautas, L. Unpaired π-spin density in defected graphite. Carbon 2002, 40, 2063-2083.
46. Ivanciuc, O.; Bytautas, L.; Klein, D. J. Mean-field resonating-valence- bond theory for unpaired π-electrons in benzenoid carbon species, J. Chem. Phys. 2002, 116, 4735-4748. Ivanciuc, O.; Klein, D. J.; Bytautas, L. Unpaired π-spin density in defected graphite. Carbon 2002, 40, 2063-2083.
47. Vukicević, D.; Randić, M.; Balaban, A. T. Partitioning of π-electrons in rings of polycyclic conjugated hydrocarbons. Part 4. Benzenoids with more than one geometric Kekulé structure corresponding to the same algebraic Kekulé structure. J. Math. Chem. 2004, in press.