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Volumn 33, Issue 1, 2009, Pages 196-206

How does non-covalent Se⋯Se=O interaction stabilize selenoxides at naphthalene 1,8-positions: Structural and theoretical investigations

Author keywords

[No Author keywords available]

Indexed keywords

NAPHTHALENE DERIVATIVE; OXYGEN; OZONE; SELENIDE; SELENIUM; SELENIUM DERIVATIVE;

EID: 58149157929     PISSN: 11440546     EISSN: 13699261     Source Type: Journal    
DOI: 10.1039/b809763a     Document Type: Article
Times cited : (16)

References (84)
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    • (1986) The Chemistry of Organic Selenium and Tellurium Compounds, Eds.
    • Bergman, J.1    Engman, L.2    Siden, J.3
  • 54
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    • Ar bond is placed almost perpendicular to the naphthyl plane, it is B when the bond is located on the plane and C is the intermediate between A and B
    • W. Nakanishi S. Hayashi T. Uehara Eur. J. Org. Chem. 2001 3933 3943
    • (2001) Eur. J. Org. Chem. , pp. 3933-3943
    • Nakanishi, W.1    Hayashi, S.2    Uehara, T.3
  • 58
  • 69
    • 0010876942 scopus 로고
    • The structures of 3b (LO) and 3a (OO) are also determined by the X-ray crystallographic analysis. The results are essentially the same as those of 1 (LO) and 1 (OO), respectively, which will be reported elsewhere Water molecules in 1 (OO) are omitted for clarity
    • J. Meinwald D. Dauplaise J. Clardy J. Am. Chem. Soc. 1977 99 7743 7744
    • (1977) J. Am. Chem. Soc. , vol.99 , pp. 7743-7744
    • Meinwald, J.1    Dauplaise, D.2    Clardy, J.3
  • 79
    • 0037954322 scopus 로고    scopus 로고
    • 6. However, the corresponding CT interactions were not detected The nonbonded Se⋯Se distance in 1 (LO) is predicted to be shorter than that of 1 (OO) by ca. 0.03 Å, while the observed values are almost equal (see Table 5). The crystal packing effect might contribute to the results
    • (2000) Comput. Chem. , vol.21 , pp. 1040-1048
    • Biegler-König, F.J.1
  • 80
    • 58149149368 scopus 로고    scopus 로고
    • The value is very close to that evaluated with the B3LYP/6-311+G(d) method
    • The value is very close to that evaluated with the B3LYP/6-311+G(d) method
  • 84
    • 58149159250 scopus 로고    scopus 로고
    • Three structures (type A, type B and type C) were optimized for each of n (OH·OH). The type C is the global minimum, which is slightly stable than type B and much stable than type A, although the steric repulsion between OH and G seems largest Eqn (R1) 36 shows that selenoxides are stabilized in this order through the non-bonded n(G)⋯σ*(Se-O) 3c-4e interactions, together with the O dependence. 16 While G = trans-MeSe is demonstrated to be most effective to stabilize in the selenoxide relative to the corresponding bis-selenide, the effect of G = cis-MeSe places between F and Cl, where the CC form is postulated for the bis-selenide
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* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.