Bond alternation in azulenes

Journal of the American Chemical Society

Volumn 122, Issue 11, 2000, Pages 2440-2445

  Lu, Yingchun ^a,b   Lemal, David M ^a,b   Jasinski, Jerry P ^a,b  

^a DARTMOUTH COLLEGE   (United States)

^b KEENE STATE COLLEGE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AZULENE DERIVATIVE; FURAN;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; HYDROGENATION; QUANTUM MECHANICS; STEREOCHEMISTRY;

EID: 0034701269     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja984113i     Document Type: Article

References (49)

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39. The Spartan package of programs was used. Hehre, W., Wavefunction, Inc.: 18401 Von Karman, Suite 370. Irvine, CA 92717.
40. The value of β′ was taken tobe 1.44 eV, calculated as follows. The ratio of the overlap integrals for the 5,10- (and 6,11-) interaction (0.0653) to that for ethylene (0.272) was multiplied by the β for ethylene (6.00), assumed to be half the AMI π-π* energy gap.
41. Rathore, R.; Lindeman, S. V.; Kumar, A. S.; Kochi, J. K. J. Am. Chem. Soc. 1998, 120, 6012.
42. Other explanations that have been advanced for bond alternation in bicycloannellated aromatics include a tendency for π electrons to distort the σ framework (Shurki, A.; Shaik, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2205. Shaik, S.; Shurki, A.; Danovich, D.; Hiberty, P. C. J. Mol. Struct. (THEOCHEM) 1997, 398-399, 155. Hiberty, P. C.; Danovich, D.; Shurki, A.; Shaik, S. J. Am. Chem. Soc. 1995, 117, 7760), nonbonded repulsion between bridgehead atoms (Jemmis, E. D.; Kiran, B. J. Org. Chem. 1996, 61, 9006), and hyperconjugation involving the bridgehead carbon bonds (ref 7).
43. Other explanations that have been advanced for bond alternation in bicycloannellated aromatics include a tendency for π electrons to distort the σ framework (Shurki, A.; Shaik, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2205. Shaik, S.; Shurki, A.; Danovich, D.; Hiberty, P. C. J. Mol. Struct. (THEOCHEM) 1997, 398-399, 155. Hiberty, P. C.; Danovich, D.; Shurki, A.; Shaik, S. J. Am. Chem. Soc. 1995, 117, 7760), nonbonded repulsion between bridgehead atoms (Jemmis, E. D.; Kiran, B. J. Org. Chem. 1996, 61, 9006), and hyperconjugation involving the bridgehead carbon bonds (ref 7).
44. Other explanations that have been advanced for bond alternation in bicycloannellated aromatics include a tendency for π electrons to distort the σ framework (Shurki, A.; Shaik, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2205. Shaik, S.; Shurki, A.; Danovich, D.; Hiberty, P. C. J. Mol. Struct. (THEOCHEM) 1997, 398-399, 155. Hiberty, P. C.; Danovich, D.; Shurki, A.; Shaik, S. J. Am. Chem. Soc. 1995, 117, 7760), nonbonded repulsion between bridgehead atoms (Jemmis, E. D.; Kiran, B. J. Org. Chem. 1996, 61, 9006), and hyperconjugation involving the bridgehead carbon bonds (ref 7).
45. Other explanations that have been advanced for bond alternation in bicycloannellated aromatics include a tendency for π electrons to distort the σ framework (Shurki, A.; Shaik, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2205. Shaik, S.; Shurki, A.; Danovich, D.; Hiberty, P. C. J. Mol. Struct. (THEOCHEM) 1997, 398-399, 155. Hiberty, P. C.; Danovich, D.; Shurki, A.; Shaik, S. J. Am. Chem. Soc. 1995, 117, 7760), nonbonded repulsion between bridgehead atoms (Jemmis, E. D.; Kiran, B. J. Org. Chem. 1996, 61, 9006), and hyperconjugation involving the bridgehead carbon bonds (ref 7).
46. Anderson, A. G.; Anderson, R. G. J. Org. Chem. 1962, 27, 3578.
47. SHELX: Sheldrick, G. M.; Kruger, C.; Goddard, R. In Crystallographic Computing 3; Oxford University Press: New York, 1985; pp 175-189.
48. All calculations were carried out with the TEXSAN, TEXRAY Structure Analysis Package, version 2.1, of Molecular Structure Corporation: The Woodlands, TX.
49. Cromer, D. T.; Waber, J. T. International Tables for X-ray Crystallography; The Kynoch Press: Birmingham, England, 1974; Vol. IV, Tables 2.3.1 and 2.2A.