Abstract
Aromaticity has played an important role in modern organic chemistry, and is one of the most frequently used and widely accepted concept for understanding, systematizing and predicting peculiarities of structure, stability, reactivity and magnetic properties of organic compounds. Aromaticity is a concept of time-dependent phenomenon and its historical development has been well reviewed recently [1–4].
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References
Minkin V.I., Glukhovtsev M.N. and Simkin B.Y. (1994) Aromaticity and Antiaromaticity. Electronic and Structural Aspects, John Wiley & Sons, New York.
Schleyer P.v.R. and Jiao H. (1996) Pure Appl. Chem. 68, 209.
Krygowski T.M., Cyranski M.K., Czarnocki Z., Hafelinger G. and Katritzky A.R. (2000) Tetrahedron 56, 1783.
Chem. Rev. special issue on aromaticity, May 2001.
Bird C.W. (1998) Tetrahedron 54, 10179.
Fokin A.A., Jiao H. and Schleyer P.v.R. (1998) J. Am. Chem. Soc. 120, 9364.
H. Jiao, P. v. R. Schleyer (1998) J. Phys. Org. Chem. 11, 655.
M. Mauksch, V. Gogonea, H. Jiao, P. v. R. Schleyer (1998) Angew. Chem. Int. Ed. 37, 2395.
V. Gogonea, P. v. R. Schleyer, P. R. Schreiner (1998) Angew. Chem. Int. Ed. 37, 1945.
H. Masui (2001) Coord. Chem. Rev. 219–221, 957.
J. R. Bleek (2001) Chem. Rev. 101, 1205.
P. v. R. Schleyer, B. Kiran, D.V. Simion, T. S. Sorensen (2000) J. Am. Chem. Soc. 122, 510.
King R.B. (2001) Chem. Rev. 101, 1119.
Bühl M. and Hirsch A. (2001) Chem. Rev. 101, 1153.
Jiao H., Schleyer P.v.R. and Glukhovtsev M.N. (1996) J. Phys. Chem. 100, 12299.
Schleyer P.v.R., Maerker C., Dransfeld A., Jiao H. and Hommes N.J.R.v.E. (1996) J. Am. Chem. Soc. 118, 6317.
Saunders M., Jiménez-Vázquez H.A., Cross R.J., Mroczkowski S., Freedberg D.L. and Anet F.A.L. (1994) Nature 367, 256.
Saunders M., Cross R.J., Jiménez-Vázquez H.A., Shimshi R. and Khong A. (1996) Science 271, 1693.
Saunders M., Jimenez-Vazquez H.A., Cross R.J., Billups W.E., Gesenberg C., Gonzalez A., Luo W., Haddon R.C., Diederich F. and Herrmann A. (1995) J. Am. Chem. Soc. 117, 9305.
Shabtai E., Weitz A., Haddon R.C., Hoffman R.E., Rabinovitz M., Khong A., Cross R.J., Saunders M., Cheng P.C. and Scott L.T. (1998) J. Am. Chem. Soc. 120, 6389.
Wang G.W., Saunders M., Khong A. and Cross R.J. (2000) J. Am. Chem. Soc. 122, 3216.
Bühl M., Thiel W., Jiao H., Schleyer P.v.R., Saunders M. and Anet F.A.L. (1994) J. Am. Chem. Soc. 116, 6005.
Bühl M. (1998) Chem. Eur. J. 4, 734.
Chen Z., Cioslowski J., Rao N., Moncrieff D., Bühl M., Hirsch A. and Thiel W. (in press) Theor. Chem. Acc.
Frisch M.J., Trucks G.W., Schlegel H.B., Scuseria G.E., Robb M.A., Cheeseman J.R., Zakrzewski V.G., Montgomery J. A. Jr., Stratmann R.E., Burant J.C., Dapprich S., Millam J.M., Daniels A.D., Kudin K.N., Strain M.C., Farkas O., Tomasi J., Barone V., Cossi M., Cammi R., Mennucci B., Pomelli C., Adamo C., Clifford S., Ochterski J., Petersson G.A., Ayala P.Y., Cui Q., Morokuma K., Malick D.K., Rabuck A.D., Raghavachari K., Foresman J.B., Cioslowski J., Ortiz J.V., Stefanov B.B., Liu G., Liashenko A., Piskorz P., Komaromi I., Gomperts R., Martin R.L., Fox D.J., Keith T., Al-Laham M.A., Peng C.Y., Nanayakkara A., Gonzalez C., Challacombe M., Gill P.M.W., Johnson B., Chen W., Wong M.W., Andres J.L., Gonzalez C., Head-Gordon M., Replogle E.S. and Pople J.A. (1998) Gaussian, Inc., Pittsburgh PA, .
Kroto H. W. and Walton D.R.M. (1993) Chem. Phys. Lett. 214, 353.
Guo T., Smalley R.E. and Scuseria G.E. (1993) J. Chem. Phys. 99, 352.
Milani C., Giambelli C., Roman H.E., Alasia F., Benedek G., Broglia R.A., Sanguinetti S. and Yabana K. (1996) Chem. Phys. Lett. 258, 554.
Fowler P.W., Heine T. and Troisi A. (1999) Chem. Phys. Lett. 312, 77.
Hollemann A.F., Wiberg E. and Wiberg N. (1995) Lehrbuch der Anorganischen Chemie, Walter de Gruyter: Berlin, New York
Almeida Murphy T., Pawlik T., Weidinger A., Höhne M., Alcala R. and Spaeth J.M. (1996) Phys. Rev. Lett. 11, 1075.
Knapp C., Dinse K.P., Pietzak B., Waiblinger M. and Weidinger A. (1997) Chem. Phys. Lett. 272, 433–437.
For theoretical background and applications, see Stone A.J. (1980) Mol. Phys. 41, 1339
Stone A.J. (1981) Inorg. Chem. 20, 563
Stone A.J. (1984) Polyhedron 3, 1299
Stone A.J. and Alderton M.J. (1982) Inorg. Chem. 21, 2297; This theory has been generalized and extended (Complementary Spherical Electron Density Model) by Mingos D.M. and Hawes J.C. (1985) in Structure and Bonding, Springer, Berlin, 1 and references therein.
Dresselhaus M.S., Dresselhaus G. and Eklund P.C. (1996) Science of Fullerenes and Carbon Nanotubes, Academic Press, San Diego.
Hirsch A. (1998) Top. Curr. Chem. 199, 1.
Ozaki M. and Takahashi A. (1986) Chem. Phys. Lett. 127, 242.
Stollhoff G. (1991) Phys. Rev. B 44, 10998.
Stollhoff G. and Scherrer H. (1995) Mater. Sci. Forum 191, 81.
Haddon R.C., Brus L.E. and Raghavachari K. (1986) Chem. Phys. Lett. 125, 459.
Hirsch A., Chen Z. and Jiao H. (2000) Angew. Chem. Int. Ed. 39, 3915.
Pasquarello A., Schlueter M. and Haddon R.C. (1992) Science 257, 1660.
Bühl M. and Anorg Z. (2000) Allg. Chem. 626, 332.
Bremer M., Schleyer P.v.R., Schoetz K., Kausch M. and Schindler M. (1987) Angew. Chem. Int. Ed. 26, 761.
Fokin A.A., Kiran B., Bremer M., Yang X., Jiao H., Schleyer P.v.R. and Schreiner P.R. (2000) Chem. Eur. J. 6, 1615.
Chen Z., Jiao H., Hirsch A. and Thiel W. (2001) J. Mol. Model. 7, 161.
Chen Z., Jiao H., Bühl M., Hirsch A. and Thiel W. (in press) Theor. Cehm. Acc.
Aihara J. (1978) J. Am. Chem. Soc. 100, 3339.
Hirsch A., Chen Z. and Jiao H. (2001) Angew. Chem. Int. Ed. 40, 2834.
Double aromaticity for planar systems, see: Schleyer P.v.R., Jiao H., Glukhovtsev M.N., Chandrasekhar J. and Kraka E. (1994) J. Am. Chem. Soc. 116, 10129;
For some recent reviews, see: Corbett J.D. (2000) Angew. Chem. Int. Ed. 39, 670.
O’Neill M.E. and Wade K. (1983) J. Mol. Struct. 103, 259.
Lohr L.L. Jr. (1981) Inorg. Chem. 20, 4229.
Belin C.H.E., Corbett J.D. and Cisar A. (1977) J. Am. Chem. Soc. 99, 7163.
Schleyer P.v.R. and Najafian K. (1998) Inorg. Chem. 37, 3454.
Li X., Kuznetsiv A.E., Zhang H.-F., Bodyrev A.I. and Wang L.-S. (2001) Science, 291, 859.
Seo D.-K. and Corbett J.D. (2001) Science 291, 841.
Kuznetsov A.E., Boldyrev A.I., Li X. and Wang L.S. (2001) J. Am. Chem. Soc. 123, 8825.
Kuznetsov A.E., Corbert J.D., Wang L.S. and Boldyrev I. (2001) Angew. Chem. Int. Ed. 40, 3369.
Fowler P.W., Havenith R.W.A. and Steiner E. (2001) Chem. Phys. Lett. 342, 85.
Juselius J., Straka M. and Sundholm D. (2001) J. Phys. Chem. A 105, 9939.
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Chen, Z., Hirsch, A., Jiao, H. (2002). Spherical Aromaticity — An Overview. In: Guldi, D.M., Martin, N. (eds) Fullerenes: From Synthesis to Optoelectronic Properties. Developments in Fullerene Science, vol 4. Springer, Dordrecht. https://doi.org/10.1007/978-94-015-9902-3_4
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DOI: https://doi.org/10.1007/978-94-015-9902-3_4
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