Septulene: The heptagonal homologue of kekulene

Angewandte Chemie - International Edition

Volumn 51, Issue 51, 2012, Pages 12795-12800

  Kumar, Bharat ^a   Viboh, Ruth L ^a   Bonifacio, Margel C ^a   Thompson, William B ^a   Buttrick, Jonathan C ^a   Westlake, Babe C ^a   Kim, Min Soo ^a   Zoellner, Robert W ^b   Varganov, Sergey A ^a   Mörschel, Philipp ^c   Teteruk, Jaroslav ^c   Schmidt, Martin U ^c   King, Benjamin T ^a  

^a UNIVERSITY OF NEVADA   (United States)

^b HUMBOLDT STATE UNIVERSITY   (United States)

^c GOETHE UNIVERSITY   (Germany)

Author keywords

aromaticity; fused ring systems; kekulenes; macrocycles; metathesis

Indexed keywords

AROMATICITIES; FUSED-RING SYSTEM; KEKULENES; MACROCYCLES; METATHESIS;

CATALYSIS;

CHEMISTRY;

EID: 84871024836     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201203266     Document Type: Article

References (46)

1. H. A. Staab, F. Diedrich, Chem. Ber. 1983, 116, 3487-3503.
2. H. A. Staab, F. Diederich, C. Krieger, D. Schweitzer, Chem. Ber. 1983, 116, 3504-3512.
3. F. Diederich, H. A. Staab, Angew. Chem. 1978, 90, 383-385
4. Angew. Chem. Int. Ed. Engl. 1978, 17, 372-374.
5. C. Krieger, F. Diederich, D. Schweitzer, H. A. Staab, Angew. Chem. 1979, 91, 733-735
6. Angew. Chem. Int. Ed. Engl. 1979, 18, 699-701.
7. L. Pauling, J. Chem. Phys. 1936, 4, 673-677.
8. R. McWeeny, Proc. Phys. Soc. London Sect. A 1951, 64, 921-930.
9. E. Clar, The Aromatic Sextet, Wiley, New York, 1972.
10. J.-M. Gilles, J. F. M. Oth, F. Sondheimer, E. P. Woo, J. Chem. Soc. B 1971, 2177-2186.
11. This conclusion is not new. Herndon discusses this point and demonstrates the utility of considering all Kekulé structures in:, W. C. Herndon, J. Am. Chem. Soc. 1973, 95, 2404-2406.
12. A. Tatibouéut, R. Hancock, M. Demeunynck, J. Lhomme, Angew. Chem. 1997, 109, 1238-1239
13. Angew. Chem. Int. Ed. Engl. 1997, 36, 1190-1191.
14. Z. E. Katsamanis, PhD thesis, Stony-Brook University (NY), 2005.
15. L. Zhou, PhD thesis, Stony-Brook University (NY), 2006.
16. I. Agranat, B. A. Hess, L. J. Schaad, Pure Appl. Chem. 1980, 52, 1399-1407.
17. IUPAC Commission on Nomenclature of Organic Chemistry, A Guide to IUPAC Nomenclature of Organic Compounds (Recommendations 1993), Blackwell Scientific Publications, Oxford, 1993.
18. M. C. Bonifacio, C. R. Robertson, J. Y. Jung, B. T. King, J. Org. Chem. 2005, 70, 8522-8526.
19. A. Iuliano, P. Piccioli, D. Febbri, Org. Lett. 2004, 6, 3711-3714.
20. S. K. Collins, A. Grandbois, M. P. Vachon, J. Côté, Angew. Chem. 2006, 118, 2989-2992
21. Angew. Chem. Int. Ed. 2006, 45, 2923-2926.
22. M. Schlosser, Chem. Ber. 1964, 3219-3233.
23. A. D. Schlüter, J. Polym. Sci. Part A 2001, 39, 1533-1556.
24. V. Hensel, K. Lützow, J. Jacob, K. Gessler, W. Saenger, A. D. Schlüter, Angew. Chem. 1997, 109, 2768-2770
25. Angew. Chem. Int. Ed. Engl. 1997, 36, 2654-2656.
26. R. Kandre, A. D. Schlüter, Macromol. Rapid Commun. 2008, 29, 1661-1665.
27. Z. Chen, C. S. Wannere, C. Corminboeuf, R. Puchta, P. von R. Schleyer, Chem. Rev. 2005, 105, 3842-3888.
28. 2) were 0.0762 (I>2σ(I)) and 0.1225 (all data). CCDC 878569 contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data-request/cif.
29. We use Mislow's definition of conformation, "a particular geometry of the molecule", not the myopic IUPAC definition, "the spatial arrangement of the atoms affording distinction between stereoisomers which can be interconverted by rotations about formally single bonds":, K. M. Mislow, Introduction to Stereochemistry, Dover Publications, Mineola, NY, 2002
30. IUPAC. Compendium of Chemical Terminology, 2 nd ed., (the "Gold Book"; Eds.: A. D. McNaught, A. Wilkinson,), Blackwell Scientific Publications, Oxford, 1997; XML on-line corrected version
31. http://goldbook.iupac.org (2006-) created by M. Nic, J. Jirat, B. Kosata; updates compiled by A. Jenkins. ISBN 0-9678550-9-8. DOI: 10.1351/goldbook.
32. DREIDING force field (, S. L. Mayo, B. D. Olafson, W. A. Goddard III, J. Phys. Chem. 1990, 94, 8897-8909) within the program suite Materials Studio
33. Materials Studio, Release 4.4, Accelrys Software Inc., San Diego, 2008).
34. These relative energies were obtained with a restricted version of DFT as implemented in GAMESS suite of programs:, M. W. Schmidt, K. K. Baldridge, J. A. Boatz, S. T. Elbert, M. S. Gordon, J. H. Jensen, S. Koseki, N. Matsunaga, K. A. Nguyen, S. J. Su, T. L. Windus, M. Dupuis, J. A. Montgomery, J. Comput. Chem. 1993, 14, 1347-1363; "Advances in electronic structure theory: GAMESS a decade later"
35. M. S. Gordon, M. W. Schmidt, in Theory and Applications of Computational Chemistry: The First Forty Years (Eds.:, C. E. Dykstra, G. Frenking, K. S. Kim, G. E. Scuseria,), Elsevier, Amsterdam, 2005, pp. 1167-1189.
36. Program CRYSCA (, M. U. Schmidt, U. Englert, J. Chem. Soc. Dalton Trans. 1996, 2077-2082), using the DREIDING force field for intermolecular interactions.
37. J. Aihara, J. Am. Chem. Soc. 1992, 114, 865-868.
38. H. Jiao, P. von R. Schleyer, Angew. Chem. 1996, 108, 2548-2551
39. Angew. Chem. Int. Ed. Engl. 1996, 35, 2383-2386.
40. C. Jerzy, O'C. Peter, F. D. Eugene, J. Am. Chem. Soc. 1991, 113, 1086-1089.
41. Omega 2.3.2, Openeye Scientific Software, Santa Fe, New Mexico (USA), 2008.
42. I. Farkas, D. Helbing, T. Vicsek, Nature 2002, 419, 131-132.
43. H. L. Strauss, Annu. Rev. Phys. Chem. 1983, 34, 301-328.
44. W. Cui, F. Li, N. L. Allinger, J. Am. Chem. Soc. 1993, 115, 2943-2951.
45. M. Shen, I. S. Ignatyev, Y. Xie, H. F. Schaefer III, J. Phys. Chem. 1993, 97, 3212-3216.
46. F. A. Carey, R. J. Sundberg, Advanced Organic Chemistry, 4 th ed., Kluwer Academic/Plenum Publishers, New York, 2000, p. 523.