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Volumn 47, Issue 11, 2008, Pages 2035-2038

Curved aromaticity of a corannulene-based neutral radical: Crystal structure and 3D unbalanced delocalization of spin

Author keywords

Aromaticity; Density functional calculations; EPR spectroscopy; Radicals; X ray diffraction

Indexed keywords

POWDERS; SPIN DYNAMICS; THREE DIMENSIONAL;

EID: 53549125539     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200704752     Document Type: Article
Times cited : (54)

References (48)
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    • Eds, B. Timanskii, O. Kalina, Kluwer Academic Publishers, Dordrecht
    • Radical Reactions of Fullerenes and their Derivatives (Eds.: B. Timanskii, O. Kalina), Kluwer Academic Publishers, Dordrecht, 2001.
    • (2001) Radical Reactions of Fullerenes and their Derivatives
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    • 2442560404 scopus 로고    scopus 로고
    • 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;
    • 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;
  • 11
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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
    • 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.
  • 12
    • 53549090132 scopus 로고    scopus 로고
    • For details of the crystal structure of 2, see the Supporting Information.
    • For details of the crystal structure of 2, see the Supporting Information.
  • 16
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    • POAV angles of the crystal structure were analyzed by mol2mol software.
    • POAV angles of the crystal structure were analyzed by mol2mol software.
  • 19
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    • For details of IR studies, see the Supporting Information
    • For details of IR studies, see the Supporting Information.
  • 20
    • 84980938251 scopus 로고    scopus 로고
    • -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;
    • -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;
  • 25
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    • For details of resonance structures, see the Supporting Information
    • For details of resonance structures, see the Supporting Information.
  • 26
    • 53549095399 scopus 로고    scopus 로고
    • 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.
    • 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.
  • 27
    • 53549100709 scopus 로고    scopus 로고
    • Details of the calculated hfccs and spin densities of 1 are found in the Supporting Information.
    • Details of the calculated hfccs and spin densities of 1 are found in the Supporting Information.
  • 29
    • 53549109416 scopus 로고    scopus 로고
    • Verdazyl and iminonitroxide derivatives have negative spin densities on this position
    • Verdazyl and iminonitroxide derivatives have negative spin densities on this position.
  • 30
    • 53549097608 scopus 로고    scopus 로고
    • For details of the magnetic measurements, see the Supporting Information
    • For details of the magnetic measurements, see the Supporting Information.
  • 31
    • 53549111580 scopus 로고    scopus 로고
    • Calculations were performed at the UB3LYP/6-31G(d,p) level using the crystal structure of 1; for details, see the Supporting Information.
    • Calculations were performed at the UB3LYP/6-31G(d,p) level using the crystal structure of 1; for details, see the Supporting Information.
  • 32
    • 53549126873 scopus 로고    scopus 로고
    • 1H ENDOR spectra, see the Supporting Information.
    • 1H ENDOR spectra, see the Supporting Information.
  • 37
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    • Angew. Chem. Int. Ed. 1998, 37, 1945-1948;
    • (1998) Angew. Chem. Int. Ed , vol.37 , pp. 1945-1948
  • 41
    • 53549125781 scopus 로고    scopus 로고
    • 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.
  • 44
    • 0036260190 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2002, 41, 1793-1796;
    • (2002) Angew. Chem. Int. Ed , vol.41 , pp. 1793-1796
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    • Angew. Chem. Int. Ed. 2005, 44, 7277-7280; see also reference [23d].
    • Angew. Chem. Int. Ed. 2005, 44, 7277-7280; see also reference [23d].
  • 47
    • 53549129706 scopus 로고    scopus 로고
    • Syntheses of corannulene derivatives with two phenoxyl moieties are underway
    • Syntheses of corannulene derivatives with two phenoxyl moieties are underway.
  • 48
    • 53549100969 scopus 로고    scopus 로고
    • 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.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.