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Is Kekulene Really Superaromatic?^†^‡

Dr. Haijun Jiao

Computer-Chemie-Centrum Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-91054 Erlangen (Germany) Fax: Int. code +(9131)859132 e-mail: [email protected]

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Prof. Dr. Paul von Ragué Schleyer,

Corresponding Author

Prof. Dr. Paul von Ragué Schleyer

Computer-Chemie-Centrum Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-91054 Erlangen (Germany) Fax: Int. code +(9131)859132 e-mail: [email protected]

Computer-Chemie-Centrum Institut für Organische Chemie der Universität Erlangen-Nürnberg Henkestrasse 42, D-91054 Erlangen (Germany) Fax: Int. code +(9131)859132 e-mail: [email protected]Search for more papers by this author

Dr. Haijun Jiao,

Dr. Haijun Jiao

Computer-Chemie-Centrum Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-91054 Erlangen (Germany) Fax: Int. code +(9131)859132 e-mail: [email protected]

Search for more papers by this author

Prof. Dr. Paul von Ragué Schleyer,

Corresponding Author

Prof. Dr. Paul von Ragué Schleyer

Computer-Chemie-Centrum Institut für Organische Chemie der Universität Erlangen-Nürnberg, Henkestrasse 42, D-91054 Erlangen (Germany) Fax: Int. code +(9131)859132 e-mail: [email protected]

First published: November 1, 1996

https://doi.org/10.1002/anie.199623831

Citations: 141

^†

This work was supported by the Fonds der Chemischen Industrie, the Deutsche Forschungsgemeinschaft, the Volkswagen-Stiftung, and Convex Computer Corporation. We also thank Prof. J. Cioslowski for discussions.

^‡

Dedicated to Professor Heinz A. Staab on the occasion of his 70th birthday

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Graphical Abstract

Kekulene is indeed a “normal” aromatic molecule. This conclusion is reached in a theoretical study in which a number of calculated properties of kekulene and reference compounds such as benzene, phenan-threne, and 1,2:7,8-dibenzanthracene were compared. Structure 1 is the most apt description of this molecule, and claims of superaromaticity can finally be laid to rest.

References

1(a) H. A. Staab, F. Diederich, Angew. Chem. 1978, 90, 383–385;
10.1002/ange.19780900513
Google Scholar
Angew. Chem. Int. Ed. Engl. 1978, 17, 372–374;
10.1002/anie.197803721
Web of Science® Google Scholar
(b) Chem. Ber. 1983, 116, 3487–3503, and references therein;
10.1002/cber.19831161021
CAS Web of Science® Google Scholar
(c) H. A. Staab, F. Diederich, C. Krieger, D. Schweitzer, Chem. Ber. 1983, 116, 3504–3512.
10.1002/cber.19831161022
CAS Web of Science® Google Scholar
2(a) G. Ege, H. Fischer, Tetrahedron 1967, 23, 149– 157;
10.1016/S0040-4020(01)83295-6
CAS Web of Science® Google Scholar
(b) G. Ege, H. Vogler, Theor. Chim. Acta. 1972, 26, 55–65;
10.1007/BF00527653
CAS Web of Science® Google Scholar
(c) J. Aihara, Bull. Chem. Soc. Jpn. 1976, 49, 1429–1430.
10.1246/bcsj.49.1429
CAS Web of Science® Google Scholar
3(a) M. Randic, Pure Appl. Chem. 1983, 55, 347;
10.1351/pac198855020347
CAS Web of Science® Google Scholar
(b) H. Vogler, J. Mol. Struct. (Theochem) 1985, 122, 333–341;
10.1016/0166-1280(85)80095-6
Google Scholar
(c) Int. J. Quantum Chem. 1986, 30, 97;
10.1002/qua.560300110
CAS Web of Science® Google Scholar
(d) P. M. Lahti, J. Org. Chem. 1988, 53, 4590–4593;
10.1021/jo00254a037
CAS Web of Science® Google Scholar
(e) N. L. Allinger, F. Li, L. Yan, J. C. Tai, J. Comput. Chem. 1990, 11, 868–895.
10.1002/jcc.540110709
CAS Web of Science® Google Scholar
4(a) J. Cioslowski, P. B. O'Connor, E. D. Fleischmann, J. Am. Chem. Soc. 1991, 113, 1086–1089;
10.1021/ja00004a005
CAS Web of Science® Google Scholar
(b) Z. Zhou, J. Phys. Org. Chem. 1995, 8, 103–107.
10.1002/poc.610080209
CAS Web of Science® Google Scholar
5(a) J. Aihara, J. Am. Chem. Soc. 1992, 114, 865–868;
10.1021/ja00029a009
CAS Web of Science® Google Scholar
(b) J. Chem. Soc. Faraday Trans. 1995, 91, 237–239.
10.1039/ft9959100237
CAS Google Scholar
6 Gaussian 94, Revision B.2: M. J. Frisch, G. W. Trucks, H. B. Schlegel, P. M. W. Gill, B. G. Johnson, M. A. Robb, J. R. Cheeseman, T. Keith, G. A. Petersson, J. A. Montgomery, K. Raghavachari, M. A. Al-Laham, V. G. Zakrzewski, J. V. Ortiz, J. B. Foresman, J. Cioslowski, B. B. Stefanov, A. Nanayakkara, M. Challacombe, C. Y. Peng, P. Y. Ayala, W. Chen, M. W. Wong, J. L. Andres, E. S. Replogle, R. Gomperts, R. L. Martin, D. J. Fox, J. S. Binkley, D. J. Defrees, J. Baker, J. P. Stewart, M. Head-Gordon, C. Gonzalez, J. A. Pople, Gaussian Inc., Pittsburgh, PA, 1995.
Google Scholar
7(a) T. A. Keith, R. F. Bader, Chem. Phys. Lett. 1992, 194, 1–8;
10.1016/0009-2614(92)85733-Q
CAS Web of Science® Google Scholar
(b) R. F. Bader, T. A. Keith, J. Chem. Phys. 1993, 99, 3683–3693.
10.1063/1.466166
CAS Web of Science® Google Scholar
8 P. von R. Schleyer, C. Maerker, A. Dransfeld, H. Jiao, N. J. R. van Eikema Hommes, J. Am. Chem. Soc. 1996, 118, 6137–6138.
Google Scholar
9 P. von R. Schleyer, H. Jiao, Pure Appl. Chem. 1996, 68, 209–218.
10.1351/pac199668020209
CAS Web of Science® Google Scholar
10(a) P. von R. Schleyer, P. K. Freeman, H. Jiao, B. Goldfuß, Angew. Chem. 1995, 107, 332–335;
10.1002/ange.19951070309
Google Scholar
Angew. Chem. Int. Ed. Engl. 1995, 34, 337–340;
10.1002/anie.199503371
CAS Web of Science® Google Scholar
(b) H. Jiao, P. von R. Schleyer in AIP Conference Proceedings 330, E.C.C.C.1, Computational Chemistry (Eds.: F. Bernardi, J.-L. Rivail), American Institut of Physics, Woodbury, NY, 1995, pp. 107–131.
Web of Science® Google Scholar
11(a) V. I. Minkin, M. N. Glukhovtsev, B. Y. Simkin, Aromaticity and Antiaromaticity, Wiley, New York, 1994;
Google Scholar
(b) P. J. Garrat, Aromaticity, Wiley, New York, 1986.
Google Scholar
12 For a discussion of homodesmic equations, see: P. George, M. Trachtman, C. W. Bock, A. M. Bret, J. Chem. Soc. Perkin Trans. 2, 1976, 1222–1227;
Google Scholar
For a more restricted subclass of homodesmic reactions, see: B. A. Hess, Jr., L. J. Schaad, J. Am. Chem. Soc. 1983, 105, 7500–7505.
10.1021/ja00364a600
CAS Web of Science® Google Scholar
13 H. J. Dauben, Jr., J. D. Wilson, J. L. Laity, Nonbenzenoid Aromaticity, Vol. II (Ed.: J. P. Snyder), Academic Press, New York, 1971, pp. 167–206, and references therein.
10.1016/B978-0-12-654002-4.50010-X
Google Scholar
14 H. Jiao, N. J. R. van Eikema Hommes, P. von R. Schleyer, A. de Meijere, J. Org. Chem. 1996, 61, 2826–2828.
10.1021/jo952028c
CAS PubMed Web of Science® Google Scholar
15 F. Sondheimer, Acc. Chem. Res. 1972, 5, 81–91.
10.1021/ar50051a001
CAS Web of Science® Google Scholar
16 J. B. Pedley, R. D. Naylor, S. P. Kirby, Thermochemical Data of Organic Compounds, 2nd ed., Chapman and Hall, London, 1986.
10.1007/978-94-009-4099-4
Google Scholar
17 R. L. Disch, J. M. Schulman, Chem. Phys. Lett. 1988, 152, 402–404.
10.1016/0009-2614(88)80114-3
CAS Web of Science® Google Scholar

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Volume35, Issue20

November 1, 1996

Pages 2383-2386

Is Kekulene Really Superaromatic?^†^‡

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Is Kekulene Really Superaromatic?^†^‡