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Volumn 7, Issue 24, 2005, Pages 4070-4081

Photoinduced intramolecular charge transfer to meta position of benzene ring in 6-aminophthalides

Author keywords

[No Author keywords available]

Indexed keywords

6 AMINOPHTHALIDE; 6-AMINOPHTHALIDE; AMINE; BENZENE DERIVATIVE; BENZOFURAN DERIVATIVE;

EID: 29844443308     PISSN: 14639076     EISSN: None     Source Type: Journal    
DOI: 10.1039/b508708b     Document Type: Article
Times cited : (18)

References (107)
  • 20
    • 29844454443 scopus 로고    scopus 로고
    • manuscript in preparation
    • Full quantum mechanical calculations study will be published elsewhere: Y. N. Svartsov and J. Karpiuk, manuscript in preparation.
    • Svartsov, Y.N.1    Karpiuk, J.2
  • 24
    • 0000810247 scopus 로고    scopus 로고
    • (b) Recently, the effect has been extended also on the directing role of the ortho substituent and now is referred to as the meta-ortho effect, see: H. E. Zimmerman, J. Phys. Chem. A, 1998, 102, 5616.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 5616
    • Zimmerman, H.E.1
  • 41
    • 0039920556 scopus 로고
    • ed. Z. Yoshida and T. Kitao, Mita Press, Tokyo
    • 3) atom and, e.g., in iso(spirobenzofuran-xanthenones) reaches even 1.527 Å as reported by M. Kubata, H. Yoshioka, K. Nakatsu, M. Matsumoto and Y. Sato, in Chemistry of Functional Dyes, ed. Z. Yoshida and T. Kitao, Mita Press, Tokyo, 1989, p. 223, compared with 1.464 Å considered to be typical C-O bond length in γ-lactones;
    • (1989) Chemistry of Functional Dyes , pp. 223
    • Kubata, M.1    Yoshioka, H.2    Nakatsu, K.3    Matsumoto, M.4    Sato, Y.5
  • 49
    • 37049123431 scopus 로고
    • ref. 20
    • (b) A slightly lower value (4.75 D) was reported by, L. H. L. Chia, H. H. Huang and Y. F. Wong, J. Chem. Soc. B, 1970, 1138; here we use the value 4.9 D as it is closer to our calculated values 5.03 D and 5.47 D, ref. 20.
    • (1970) J. Chem. Soc. B , pp. 1138
    • Chia, L.H.L.1    Huang, H.H.2    Wong, Y.F.3
  • 50
    • 29844450406 scopus 로고    scopus 로고
    • note
    • The value 130° has been obtained from comparison of phthalide geometry from crystal structure study published in ref. 40, with that of methyl benzoate. As to our knowledge there is no direct crystal structure data for methyl benzoate, we used average value of the COC angle derived from structures found in the Cambridge Crystallographic Data Centre database where MB was part of a molecular complex.
  • 54
    • 29844447135 scopus 로고    scopus 로고
    • note
    • -1 on going from hexane to DMSO.
  • 55
    • 29844456542 scopus 로고    scopus 로고
    • J. Karpiuk and Y. N. Svartsov, work in progress
    • J. Karpiuk and Y. N. Svartsov, work in progress.
  • 74
    • 0003397206 scopus 로고
    • eds. O. C. Van Belle, P. Bordewijk and A. Rip, Elsevier, Amsterdam
    • C. J. F. Böttcher, in Theory of Electric Polarization,eds. O. C. Van Belle, P. Bordewijk and A. Rip, Elsevier, Amsterdam, 1973, Vol. 1.
    • (1973) Theory of Electric Polarization , vol.1
    • Böttcher, C.J.F.1
  • 75
    • 0001269334 scopus 로고
    • ed. E. C. Lim, Academic Press, New York
    • W. Liptay, in Excited states, ed. E. C. Lim, Academic Press, New York, 1974, p. 129.
    • (1974) Excited States , pp. 129
    • Liptay, W.1
  • 93
    • 29844446980 scopus 로고    scopus 로고
    • note
    • O are van der Waals radii of those atoms, respectively.
  • 95
    • 29844444498 scopus 로고    scopus 로고
    • note
    • e = 11.6 D and α = 26° have been obtained.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.