The Quinones of Azulene. A Theoretical Prognosis

Journal of the American Chemical Society

Volumn 102, Issue 16, 1980, Pages 5169-5176

  Scott, Lawrence T ^a   Rozeboom, Melvin D ^b   Houk, K N ^b   Fukunaga, T ^c   Jórg Lindner, Hans ^d   Hafnerld, Klaus ^d  

^a UNIVERSITY OF NEVADA   (United States)

^b LOUISIANA STATE UNIVERSITY   (United States)

^c DARMSTADT UNIVERSITY OF TECHNOLOGY   (Germany)

^d DUPONT COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000756257     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00536a007     Document Type: Article

References (71)

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50. A strain energy of 18,7 kcal/mol was assumed for the azuloquinones and 2.6 kcal/mol for the naphthoquinones. These values were estimated from Allinger's potentials for bending strain [Allinger, N. L.; Tribble, M. T.; Miller, M. A.; Werz, D. H. J. Am Chem. Soc. 1971, 93, 1637-1648] applied to MINDO/3-optimized geometries of 26-AQ and 26-NQ, respectively, and seem in line with the previously quoted value of 16 kcal/mol for the strain energy of azulene [Streitwieser, A., Jr. “Molecular Orbital Theory for Organic Chemists”; Wiley: New York, 1961; p 244].
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66. See, for example, Borden, W. T. “Modern Molecular Orbital Theory for Organic Chemists”; Prentice-Hall: Englewood Cliffs, N.J., 1975; Chapter 7. The program used for these calculations was written by Simmons (Simmons, H. E. Prog. Org. Chem. 1970, 7, 1) and extensively modified by M. D. Gordon. Two-center integrals were calculated by the method of Nishimoto and Mataga (Nishimoto, K.; Mataga, N. Z. Phys. Chem. (Frankfurt am Main) 1957, 12, 335), and core resonance integrals were calculated by the method of Nishimoto and Forster (Nishimoto, K.; Forster, L. S. Theor. Chim. Acta 1965, 3, 407). Ionization potentials and one-center electron repulsion integrals were taken as-11.16 and 11.13 eV for carbon and-17.70 and 15.23 eV for oxygen.
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70. Pentalene X-ray: Kitschke, B.; Lindner, H. J. Tetrahedron Lett. 1977, 2511. See also: Bischof, P.; Gleiter, R.; Hafner, K.; Knauer, K. H.; Spanget-Larsen, J.; Suss, H. U. Chem. Ber. 1978, 111, 932.
71. Hückel calculations on all the DQs as well as the pentalenequinones and cyclooctatetraenequinones have been carried out by one of use (T.F.), and are available upon request to him.