The Impact of Antiaromatic Subunits in [4 n +2] π-Systems: Bispentalenes with [4 n +2] π-Electron Perimeters and Antiaromatic Character

Journal of the American Chemical Society

Volumn 137, Issue 22, 2015, Pages 7178-7188

  Cao, Jing ^a   London, Gábor ^a,d   Dumele, Oliver ^a   Von Wantoch Rekowski, Margarete ^a   Trapp, Nils ^a   Ruhlmann, Laurent ^b   Boudon, Corinne ^b   Stanger, Amnon ^c   Diederich, François ^a  

^a ETH ZURICH   (Switzerland)

^b UNIVERSITÉ DE STRASBOURG   (France)

^c TECHNION ISRAEL INSTITUTE OF TECHNOLOGY   (Israel)

^d UNIVERSITY OF SZEGED   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; CHEMICAL BONDS; CHROMOPHORES; MUSCULOSKELETAL SYSTEM; NAPHTHALENE; NUCLEAR MAGNETIC RESONANCE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; SULFUR COMPOUNDS; X RAY DIFFRACTION; X RAY DIFFRACTION ANALYSIS;

ANTIAROMATIC CHARACTER; COMPUTATIONAL RESULTS; DOUBLE CARBOPALLADATION; ELECTROCHEMICAL DATA; HOMO-LUMO ENERGY GAP; MOLECULAR PROPERTIES; NAPHTHALENE MOIETIES; SPECTRAL PROPERTIES;

ELECTRONS;

BENZENE; BISPENTALENE DERIVATIVE; CYCLOPENTADIENE DERIVATIVE; HYDROCARBON; NAPHTHALENE; PROTON; UNCLASSIFIED DRUG;

ARTICLE; CALCULATION; CHEMICAL BINDING; CHEMICAL REACTION; CHROMATOPHORE; ELECTROCHEMICAL ANALYSIS; ELECTRON; ENERGY; PERIMETER; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THERMOSTABILITY; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 84935827767     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/jacs.5b03074     Document Type: Article

References (87)

1. Garratt, P. J. Aromaticity; John Wiley and Sons: New York, 1986.
2. Minkin, V. I.; Glukhovtsev, M. N.; Simkin, B. Y. Aromaticity and Antiaromaticity; John Wiley and Sons: New York, 1994.
3. Allen, A. D.; Tidwell, T. T. Chem. Rev. 2001, 101, 1333 - 1348
4. Gomes, J. A. N. F.; Mallion, R. B. Chem. Rev. 2001, 101, 1349 - 1383
5. Gleiter, R.; Haberhauer, G. Aromaticity and Other Conjugation Effects; Wiley-VCH: Weinheim, Germany, 2012.
6. Hückel, E. Z. Z. Phys. 1931, 70, 204 - 286
7. Hückel, E. Z. Z. Phys. 1932, 76, 628 - 648
8. Hückel, E. Z. Z. Electrochem. 1937, 43, 752 - 788
9. Frost, A. A.; Musulin, B. J. Chem. Phys. 1953, 21, 572 - 573
10. Breslow, R. Chem. Eng. News 1965, 43, 90 - 100
11. Breslow, R. Acc. Chem. Res. 1973, 6, 393 - 398
12. Krygowski, T. M.; Cyrañski, M. K.; Czarnocki, Z.; Häfelinger, G.; Katritzky, A. R. Tetrahedron 2000, 56, 1783 - 1796
13. Schleyer, P. v. R.; Jiao, H. Pure Appl. Chem. 1996, 68, 209 - 218
14. Cyrañski, M. K.; Krygowski, T. M.; Katritzky, A. R.; Schleyer, P. v. R. J. Org. Chem. 2002, 67, 1333 - 1338
15. Stanger, A. Chem. Commun. 2009, 1939 - 1947
16. Zahradnik, R. Angew. Chem., Int. Ed. 1965, 4, 1039 - 1050
17. Bochvar, D. A.; Gal'pern, E. G.; Gambaryan, N. P. Bull. Acad. Sci. USSR, Div. Chem. Sci. 1970, 19, 377 - 379
18. Randić, M. J. Am. Chem. Soc. 1977, 99, 444 - 450
19. Randić, M. Chem. Rev. 2003, 103, 3449 - 3605
20. Stowasser, B.; Hafner, K. Angew. Chem., Int. Ed. Engl. 1986, 25, 466 - 468
21. Hoheisel, T. N.; Schrettl, S.; Szilluweit, R.; Frauenrath, H. Angew. Chem., Int. Ed. 2010, 49, 6496 - 6515
22. Pisula, W.; Feng, X.; Müllen, K. Chem. Mater. 2011, 23, 554 - 567
23. Figueira-Duarte, T. M.; Müllen, K. Chem. Rev. 2011, 111, 7260 - 7314
24. Henson, Z. B.; Müllen, K.; Bazan, G. C. Nat. Chem. 2012, 4, 699 - 704
25. Wang, C.; Dong, H.; Hu, W.; Liu, Y.; Zhu, D. Chem. Rev. 2012, 112, 2208 - 2267
26. Mei, J.; Diao, Y.; Appleton, A. L.; Fang, L.; Bao, Z. J. Am. Chem. Soc. 2013, 135, 6724 - 6746
27. Coppo, P.; Yeates, S. G. Adv. Mater. 2005, 17, 3001 - 3005
28. Anthony, J. E. Chem. Rev. 2006, 106, 5028 - 5048
29. Palayangoda, S. S.; Mondal, R.; Shah, B. K.; Neckers, D. C. J. Org. Chem. 2007, 72, 6584 - 6587
30. Anthony, J. E. Angew. Chem., Int. Ed. 2008, 47, 452 - 483
31. Kaur, I.; Jia, W.; Kopreski, R. P.; Selvarasah, S.; Dokmeci, M. R.; Pramanik, C.; McGruer, N. E.; Miller, G. P. J. Am. Chem. Soc. 2008, 130, 16274 - 16286
32. Breslow, R.; Foss, F. W., Jr. J. Phys.: Condens. Matter 2008, 20, 374104
33. Breslow, R.; Schneebeli, S. T. Tetrahedron 2011, 67, 10171 - 10178
34. Pho, T. V.; Yuen, J. D.; Kurzman, J. A.; Smith, B. G.; Miao, M.; Walker, W. T.; Seshadri, R.; Wudl, F. J. Am. Chem. Soc. 2012, 134, 18185 - 18188
35. Bunz, U. H. F.; Engelhart, J. U.; Lindner, B. D.; Schaffroth, M. Angew. Chem., Int. Ed. 2013, 52, 3810 - 3821
36. Jiang, W.; Li, Y.; Wang, Z. Chem. Soc. Rev. 2013, 42, 6113 - 6127
37. Yue, W.; Suraru, S.-L.; Bialas, D.; Müller, M.; Würthner, F. Angew. Chem., Int. Ed. 2014, 53, 6159 - 6162
38. Engelhart, J. U.; Tverskoy, O.; Bunz, U. H. F. J. Am. Chem. Soc. 2014, 136, 15166 - 15169
39. Feng, C.-N.; Kuo, M.-Y.; Wu, Y.-T. Angew. Chem., Int. Ed. 2013, 52, 7791 - 7794
40. Yang, X.; Liu, D.; Miao, Q. Angew. Chem., Int. Ed. 2014, 53, 6786 - 6790
41. Chase, D. T.; Rose, B. D.; McClintock, S. P.; Zakharov, L. N.; Haley, M. M. Angew. Chem., Int. Ed. 2011, 50, 1127 - 1130
42. Chase, D. T.; Fix, A. G.; Kang, S. J.; Rose, B. D.; Weber, C. D.; Zhong, Y.; Zakharov, L. N.; Lonergan, M. C.; Nuckolls, C.; Haley, M. M. J. Am. Chem. Soc. 2012, 134, 10349 - 10352
43. Nishida, J.; Tsukaguchi, S.; Yamashita, Y. Chem.-Eur. J. 2012, 18, 8964 - 8970
44. Fix, A. G.; Deal, P. E.; Vonnegut, C. L.; Rose, B. D.; Zakharov, L. N.; Haley, M. M. Org. Lett. 2013, 15, 1362 - 1365
45. Shimizu, A.; Kishi, R.; Nakano, M.; Shiomi, D.; Sato, K.; Takui, T.; Hisaki, I.; Miyata, M.; Tobe, Y. Angew. Chem., Int. Ed. 2013, 52, 6076 - 6079
46. Tobe, Y. Chem. Rec. 2015, 15, 86 - 96
47. Müller, E.; Fritz, H.-G.; Munk, K.; Straub, H.; Geisel, M. v. H. Tetrahedron Lett. 1969, 10, 5167 - 5170
48. Scherf, U.; Müllen, K. Polymer 1992, 33, 2443 - 2446
49. Levi, Z. U.; Tilley, T. D. J. Am. Chem. Soc. 2010, 132, 11012 - 11014
50. Bally, T.; Chai, S.; Neuenschwander, M.; Zhu, Z. J. Am. Chem. Soc. 1997, 119, 1869 - 1875
51. Fowler, P. W.; Soncini, A. Polycyclic Aromat. Compd. 2004, 24, 353 - 366
52. Cuesta, I. G.; Ligabue, A.; Sánchez de Merás, A.; Lazzeretti, P. Chem. Phys. Lett. 2005, 401, 282 - 287
53. Le Goff, E. J. Am. Chem. Soc. 1962, 84, 3975 - 3976
54. Hafner, K.; Bangert, K. F.; Orfanos, V. Angew. Chem., Int. Ed. 1967, 6, 451 - 452
55. Hafner, K.; Süss, H. U. Angew. Chem., Int. Ed. 1973, 12, 575 - 577
56. Hafner, K.; Suda, M. Angew. Chem., Int. Ed. Engl. 1976, 15, 314 - 315
57. Hafner, K.; Goltz, M. Angew. Chem., Int. Ed. Engl. 1982, 21, 695 - 696
58. Kawase, T.; Fujiwara, T.; Kitamura, C.; Konishi, A.; Hirao, Y.; Matsumoto, K.; Kurata, H.; Kubo, T.; Shinamura, S.; Mori, H.; Miyazaki, E.; Takimiya, K. Angew. Chem., Int. Ed. 2010, 49, 7728 - 7732
59. Hashmi, A.; Stephen, K.; Wieteck, M.; Braun, I.; Nösel, P.; Jongbloed, L.; Rudolph, M.; Rominger, F. Adv. Synth. Catal. 2012, 354, 555 - 562
60. Maekawa, T.; Segawa, Y.; Itami, K. Chem. Sci. 2013, 4, 2369 - 2373
61. Zhao, J.; Oniwa, K.; Asao, N.; Yamamoto, Y.; Jin, T. J. Am. Chem. Soc. 2013, 135, 10222 - 10225
62. Shen, J.; Yuan, D.; Qiao, Y.; Shen, X.; Zhang, Z.; Zhong, Y.; Yi, Y.; Zhu, X. Org. Lett. 2014, 16, 4924 - 4927
63. Nakano, M.; Osaka, I.; Takimiya, K. J. Mater. Chem. C 2015, 3, 283 - 290
64. Dai, G.; Chang, J.; Zhang, W.; Bai, S.; Huang, K.-W.; Xu, J.; Chi, C. Chem. Commun. 2015, 51, 503 - 506
65. Chen, C.; Harhausen, M.; Liedtke, R.; Bussmann, K.; Fukazawa, A.; Yamaguchi, S.; Petersen, J. L.; Daniliuc, C. G.; Fröhlich, R.; Kehr, G.; Erker, G. Angew. Chem., Int. Ed. 2013, 52, 5992 - 5996
66. Chen, C.; Harhausen, M.; Fukazawa, A.; Yamaguchi, S.; Fröhlich, R.; Daniliuc, C. G.; Petersen, J. L.; Kehr, G.; Erker, G. Chem.-Asian J. 2014, 9, 1671 - 1681
67. Zhang, H.; Karasawa, T.; Yamada, H.; Wakamiya, A.; Yamaguchi, S. Org. Lett. 2009, 11, 3076 - 3079
68. Saito, M.; Hashimoto, Y.; Tajima, T.; Ishimura, K.; Nagase, S.; Minoura, M. Chem.-Asian J. 2012, 7, 480 - 483
69. Xu, F.; Peng, L.; Orita, A.; Otera, J. Org. Lett. 2012, 14, 3970 - 3973
70. Nakano, M.; Osaka, I.; Takimiya, K.; Koganezawa, T. J. Mater. Chem. C 2014, 2, 64 - 70
71. Rivera-Fuentes, P.; von Wantoch Rekowski, M.; Schweizer, W. B.; Gisselbrecht, J.-P.; Boudon, C.; Diederich, F. Org. Lett. 2012, 14, 4066 - 4069
72. London, G.; von Wantoch Rekowski, M.; Dumele, O.; Schweizer, W. B.; Gisselbrecht, J.-P.; Boudon, C.; Diederich, F. Chem. Sci. 2014, 5, 965 - 972
73. Gershoni-Poranne, R.; Stanger, A. Chem.-Eur. J. 2014, 20, 5673 - 5688
74. Chelucci, G. Chem. Rev. 2012, 112, 1344 - 1462
75. Pople, J. A.; Untch, K. G. J. Am. Chem. Soc. 1966, 88, 4811 - 4815
76. Dauben, H. J., Jr.; Wilson, J. D.; Laity, J. L. J. Am. Chem. Soc. 1968, 90, 811 - 813
77. Schleyer, P. v. R.; Maerker, C.; Dransfeld, A.; Jiao, H.; van Eikema Hommes, N. J. R. J. Am. Chem. Soc. 1996, 118, 6317 - 6318
78. Chen, Z.; Wannere, C. S.; Corminboeuf, C.; Puchta, R.; Schleyer, P. v. R. Chem. Rev. 2005, 105, 3842 - 3888
79. Bultinck, P. Faraday Discuss. 2007, 135, 347 - 365
80. Schleyer, P. v. R.; Wu, J. I.; Cossío, F. P.; Fernández, I. Chem. Soc. Rev. 2014, 43, 4909 - 4921
81. Ring current of X ppm means an induced ring current that produces an induced magnetic field which give rise to NICS(1.7)π,ZZ of X ppm. This terminology is used from now on when quantitative comparisons are wished.
82. Smith, M. B.; March, J. March's Advanced Organic Chemistry, 6 th ed.; John Wiley & Sons: New York, 2007; Chapters 1 and 2, pp 3 - 105.
83. Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A., Jr.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, M. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision D.01; Gaussian, Inc.: Wallingford, CT, 2013.
84. Laurent, A. D.; Jacquemin, D. Int. J. Quantum Chem. 2013, 113, 2019 - 2039
85. Pommerehne, J.; Vestweber, H.; Guss, W.; Mahrt, R. F.; Bässler, H.; Porsch, M.; Daub, J. Adv. Mater. 1995, 7, 551 - 554
86. D'Andrade, B. W.; Datta, S.; Forrest, S. R.; Djurovich, P.; Polikarpov, E.; Thompson, M. E. Org. Electron. 2005, 6, 11 - 20
87. Watanabe, M.; Chang, Y. J.; Liu, S.-W.; Chao, T.-H.; Goto, K.; Islam, M. M.; Yuan, C.-H.; Tao, Y.-H.; Shinmyozu, T.; Chow, T. J. Nat. Chem. 2012, 4, 574 - 578