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Volumn 43, Issue 32, 2004, Pages 4200-4206

Aromaticity: The the alternating C-C bond length structures of [14]-, [18]- and [22]annulene

Author keywords

Annulenes; Aromaticity; Density functional calculations; NMR spectroscopy; Structure elucidation

Indexed keywords

CARBON; CHEMICAL BONDS; NUCLEAR MAGNETIC RESONANCE;

EID: 4644338165     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200454188     Document Type: Article
Times cited : (137)

References (59)
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    • In 1980, Haddon noted that the 1965 X-ray study of [18]annulene "cannot not be regarded as definitive" as the C-C separations are averaged over time. R. C. Haddon, Chem. Phys. Lett. 1980, 70, 210.
    • (1980) Chem. Phys. Lett. , vol.70 , pp. 210
    • Haddon, R.C.1
  • 33
    • 4644283579 scopus 로고    scopus 로고
    • The X-ray structures of [14]- and [18] annulene were retrieved from the Cambridge Crystallographic Data Center (www.ccdc.cam.ac.uk/conts/retrieving.html (the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax: (+44)1223-336-033; or deposit@ccdc.cam. ac.uk)).
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    • 4644364140 scopus 로고    scopus 로고
    • personal communication to P. von R. Schleyer
    • b) C. D. Stevenson, personal communication to P. von R. Schleyer.
    • Stevenson, C.D.1
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    • note
    • 2 structures in detail using LMO-dissection and find that these are due about half to the local shielding influences of the nearby bonds and the other half are due to the sum of small remote effects.
  • 42
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    • personal communication to P. von R. Schleyer
    • S. Grimme, personal communication to P. von R. Schleyer.
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    • 4644283228 scopus 로고    scopus 로고
    • note
    • Structures and energies of all [10]annulene conformations employing various density functional methods with the 6-311 + G** basis set are reported in the Supporting Information.
  • 49
    • 0000862640 scopus 로고
    • E. Vogel, H. D. Roth, Angew. Chem. 1964, 76, 145; Angew. Chem. Int. Ed. Engl. 1964, 3, 228.
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    • E. Vogel, H. D. Roth, Angew. Chem. 1964, 76, 145; Angew. Chem. Int. Ed. Engl. 1964, 3, 228.
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    • note
    • 1) both have delocalized structures but with moderate C-C bond-length differences (Δr = 0.039 and 0.061 Å, respectively, at KMLYP). Optimized geometries of various bridged annulenes are reported in the Supporting Information.
  • 53
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    • note
    • 1H NMR chemical shifts were computed at GIAO[46]-B3LYP/6-311 + G**//using the DFT/6-311+G** geometry. The expected absolute proton shieldings, σ, were converted into chemical shifts, δ, as the difference from the proton shieldings of TMS, 31.98 ppm.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.