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Volumn 45, Issue 23, 2004, Pages 4553-4558

peri-Interaction between diarylmethyl and diarylmethylium units in 1,8-disubstituted naphthalenes: Preference of localized structure for the C-H bridged carbocation

Author keywords

Carbocation; Hydride shift; peri Interaction; Three centered two electron bond; Triarylmethylium

Indexed keywords

BRIDGED COMPOUND; CARBON; HYDROGEN; NAPHTHALENE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

EID: 2442536187     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.002     Document Type: Article
Times cited : (26)

References (39)
  • 23
    • 2442587181 scopus 로고    scopus 로고
    • note
    • 2)
  • 24
    • 2442572671 scopus 로고    scopus 로고
    • note
    • Hexaphenylethanes are notorious for giving the disordered crystal structures around the inner C-C bond due to the 'globular' molecular shape (Ref. 14). Since the carbocations 2 possess the similar structural features, there will be high possibility that the C-H ⋯ C part in 2 with four aryl groups of a kind suffers from positional disorder in crystal, thus preventing the chance to tell the localized structure from the delocalized one by X-ray analysis
  • 27
    • 2442423762 scopus 로고    scopus 로고
    • note
    • abstract
  • 28
    • 2442425883 scopus 로고    scopus 로고
    • note
    • +)
  • 30
    • 2442438446 scopus 로고    scopus 로고
    • note
    • 4Li are also due to the similar by-production of such abnormal adducts
  • 31
    • 2442551412 scopus 로고    scopus 로고
    • note
    • -1, T=153 K. The final R value is 0.069 for 8195 independent reflections with I>3σI and 757 parameters
  • 32
    • 2442614591 scopus 로고    scopus 로고
    • note
    • C 177 and 176 ppm, respectively) are close to that of 8 (175 ppm), which is also in consonant with this structural assignment
  • 33
    • 0003438540 scopus 로고
    • The Nature of Chemical Bond
    • Ithaca, NY: Cornell University Press. p 260
    • Pauling L. The Nature of Chemical Bond. 3rd ed. 1960;Cornell University Press, Ithaca, NY. p 260
    • (1960) 3rd Ed.
    • Pauling, L.1
  • 38
    • 2442501092 scopus 로고    scopus 로고
    • note
    • ′ under acidic conditions observed here also conflicts with their view that 2b/3b might be unstable against acid with forming dication 5b. We are not sure that such drastic changes in reactivity come from the different substituents on the aryl groups
  • 39
    • 0001432693 scopus 로고
    • + contact, that prefers the C-H localized structure rather than the delocalized one with a three-centered-four-electron bond
    • + contact, that prefers the C-H localized structure rather than the delocalized one with a three-centered-four-electron bond Arduengo A.J. III, Gamper S.F., Tamm M., Calabrese J.C., Davidson F., Craig H.A. J. Am. Chem. Soc. 117:1995;572
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 572
    • Arduengo III, A.J.1    Gamper, S.F.2    Tamm, M.3    Calabrese, J.C.4    Davidson, F.5    Craig, H.A.6


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.