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2442560404
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Corannulene derivatives with a verdazyl or iminonitroxide moiety have poor crystallinity and show small amounts of spin delocalization onto the curved π-conjugated system; see: a Y. Morita, S. Nishida, T. Kobayashi, K. Fukui, K. Sato, D. Shiomi, T. Takui, K. Nakasuji, Org. Lett. 2004, 6, 1397-1400;
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Corannulene derivatives with a verdazyl or iminonitroxide moiety have poor crystallinity and show small amounts of spin delocalization onto the curved π-conjugated system; see: a) Y. Morita, S. Nishida, T. Kobayashi, K. Fukui, K. Sato, D. Shiomi, T. Takui, K. Nakasuji, Org. Lett. 2004, 6, 1397-1400;
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9
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Sato, K.6
Shiomi, D.7
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11
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53549118266
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To our knowledge, this is not only the first crystal structure of a neutral radical with curved p conjugation, but also the first example of a crystal structure of a phenoxyl radical except for galvinoxyl
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To our knowledge, this is not only the first crystal structure of a neutral radical with curved p conjugation, but also the first example of a crystal structure of a phenoxyl radical except for galvinoxyl.
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12
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53549090132
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For details of the crystal structure of 2, see the Supporting Information.
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For details of the crystal structure of 2, see the Supporting Information.
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16
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53549123245
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POAV angles of the crystal structure were analyzed by mol2mol software.
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POAV angles of the crystal structure were analyzed by mol2mol software.
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18
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0025781198
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b) R. West, J. A. Jorgensen, K. L. Stearley, J. C. Calabrese, J. Chem. Soc. Chem. Commun. 1991, 1234-1235.
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19
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53549113016
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For details of IR studies, see the Supporting Information
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For details of IR studies, see the Supporting Information.
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20
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84980938251
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-1 of phenoxyl radicals in the solid state or in solution was assigned to the C-O vibration; see: a E. Müller, K. Ley, Chem. Ber. 1954, 87, 922-934;
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-1 of phenoxyl radicals in the solid state or in solution was assigned to the C-O vibration; see: a) E. Müller, K. Ley, Chem. Ber. 1954, 87, 922-934;
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23
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84981759285
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25
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53549116716
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For details of resonance structures, see the Supporting Information
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For details of resonance structures, see the Supporting Information.
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26
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53549095399
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All DFT calculations were performed with the Gaussian03 program (revision B.05) Gaussian, Inc., Wallingford CT, 2004; the full reference is listed in the Supporting Information.
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All DFT calculations were performed with the Gaussian03 program (revision B.05) Gaussian, Inc., Wallingford CT, 2004; the full reference is listed in the Supporting Information.
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27
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53549100709
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Details of the calculated hfccs and spin densities of 1 are found in the Supporting Information.
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Details of the calculated hfccs and spin densities of 1 are found in the Supporting Information.
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28
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27644479652
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K. Fukui, Y. Morita, S. Nishida, T. Kobayashi, K. Sato, D. Shiomi, T. Takui, K. Nakasuji, Polyhedron 2005, 24, 2326-2329.
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Fukui, K.1
Morita, Y.2
Nishida, S.3
Kobayashi, T.4
Sato, K.5
Shiomi, D.6
Takui, T.7
Nakasuji, K.8
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29
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53549109416
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Verdazyl and iminonitroxide derivatives have negative spin densities on this position
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Verdazyl and iminonitroxide derivatives have negative spin densities on this position.
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30
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53549097608
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For details of the magnetic measurements, see the Supporting Information
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For details of the magnetic measurements, see the Supporting Information.
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31
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53549111580
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Calculations were performed at the UB3LYP/6-31G(d,p) level using the crystal structure of 1; for details, see the Supporting Information.
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Calculations were performed at the UB3LYP/6-31G(d,p) level using the crystal structure of 1; for details, see the Supporting Information.
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32
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53549126873
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1H ENDOR spectra, see the Supporting Information.
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1H ENDOR spectra, see the Supporting Information.
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33
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0011190497
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41
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53549125781
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UV/Vis studies for 1 and 2 demonstrate a sizable p conjugation between the corannulene and the phenoxyl moieties of 1; for details, see the Supporting Information.
-
UV/Vis studies for 1 and 2 demonstrate a sizable p conjugation between the corannulene and the phenoxyl moieties of 1; for details, see the Supporting Information.
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42
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0034679043
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a) Y. Morita, T. Ohba, N. Haneda, S. Maki, J. Kawai, K. Hatanaka, K. Sato, D. Shiomi, T. Takui, K. Nakasuji, J. Am. Chem. Soc. 2000, 122, 4825-4826;
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0142223684
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b) Y. Morita, T. Aoki, K. Fukui, S. Nakazawa, K. Tamaki, S. Suzuki, A. Fuyuhiro, K. Yamamoto, K. Sato, D. Shiomi, A. Naito, T. Takui, K. Nakasuji, Angew. Chem. 2002, 114, 1871-1874;
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34247538143
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27844519388
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Angew. Chem. Int. Ed. 2005, 44, 7277-7280; see also reference [23d].
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Angew. Chem. Int. Ed. 2005, 44, 7277-7280; see also reference [23d].
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47
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53549129706
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Syntheses of corannulene derivatives with two phenoxyl moieties are underway
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Syntheses of corannulene derivatives with two phenoxyl moieties are underway.
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48
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53549100969
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Bowl-to-bowl inversions of corannulene derivatives with closed-shell systems have been studied extensively; see reference [1a] and references therein
-
Bowl-to-bowl inversions of corannulene derivatives with closed-shell systems have been studied extensively; see reference [1a] and references therein.
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