메뉴 건너뛰기




Volumn 5, Issue 22, 2003, Pages 4141-4144

Pyrazine Analogues of Dipyrrolylquinoxalines

Author keywords

[No Author keywords available]

Indexed keywords

PYRAZINE DERIVATIVE; QUINOXALINE DERIVATIVE;

EID: 0345376250     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0355635     Document Type: Article
Times cited : (48)

References (16)
  • 6
    • 0033544362 scopus 로고    scopus 로고
    • Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438. Mizuno, T.; Wei, W.-H.; Eller, L. R.; Sessler, J. L. J. Am. Chem. Soc. 2002, 124, 1134. Kirkovits, G. J.; Zimmerman, R. S.; Huggins, M. T.; Lynch, V. M.; Sessler, J. L. Eur. J. Org. Chem. 2002, 3768.
    • (1999) J. Am. Chem. Soc. , vol.121 , pp. 10438
    • Black, C.B.1    Andrioletti, B.2    Try, A.C.3    Ruiperez, C.4    Sessler, J.L.5
  • 7
    • 0037138622 scopus 로고    scopus 로고
    • Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438. Mizuno, T.; Wei, W.-H.; Eller, L. R.; Sessler, J. L. J. Am. Chem. Soc. 2002, 124, 1134. Kirkovits, G. J.; Zimmerman, R. S.; Huggins, M. T.; Lynch, V. M.; Sessler, J. L. Eur. J. Org. Chem. 2002, 3768.
    • (2002) J. Am. Chem. Soc. , vol.124 , pp. 1134
    • Mizuno, T.1    Wei, W.-H.2    Eller, L.R.3    Sessler, J.L.4
  • 8
    • 0036859323 scopus 로고    scopus 로고
    • Black, C. B.; Andrioletti, B.; Try, A. C.; Ruiperez, C.; Sessler, J. L. J. Am. Chem. Soc. 1999, 121, 10438. Mizuno, T.; Wei, W.-H.; Eller, L. R.; Sessler, J. L. J. Am. Chem. Soc. 2002, 124, 1134. Kirkovits, G. J.; Zimmerman, R. S.; Huggins, M. T.; Lynch, V. M.; Sessler, J. L. Eur. J. Org. Chem. 2002, 3768.
    • (2002) Eur. J. Org. Chem. , pp. 3768
    • Kirkovits, G.J.1    Zimmerman, R.S.2    Huggins, M.T.3    Lynch, V.M.4    Sessler, J.L.5
  • 11
    • 0344668790 scopus 로고    scopus 로고
    • note
    • w = 0.1186 (all data), CCDC 217630. See the Supporting Information for CIF files.
  • 13
    • 0037938786 scopus 로고    scopus 로고
    • Bucher, C.; Zimmerman, R. S.; Lynch, V.; Kral, V.; Sessler, J. L J. Am. Chem. Soc. 2001, 123, 2099. Sessler, J. L.; Camiolo, S.; Gale, P. A. Coord. Chem. Rev. 2003, 240, 17.
    • (2003) Coord. Chem. Rev. , vol.240 , pp. 17
    • Sessler, J.L.1    Camiolo, S.2    Gale, P.A.3
  • 16
    • 0345531060 scopus 로고    scopus 로고
    • note
    • We performed molecular modeling calculations, using HyperChem, v7.1 in order to calculate the rotational barrier for the C2-C6 and C11-C12 bonds (numbering of the atoms is according with the X-ray structure). We used the di-tert-butyl analogues of both 7 and 8 so as to keep the calculations tractable. The PM3 semiempirical method in conjunction with the Conformation Search module was used to determine the structure with the minimum energy. The criteria for convergence was a difference in energy between two sequential structures below 0.01 kcal/(A mol). The results of these calculation show that the rotational barrier is 37% higher in the case of 8 vs 7. This is consistent with preorganization and conformation affects being significant aryl bridged dipyrrole anion receptors, and more so in the case of the larger dipyrrolylquinoxalines than in the smaller dipyrrolylpyrazines.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.