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Volumn 12, Issue 10, 2006, Pages 2745-2751

Can substituted cyclopentadiene become aromatic or antiaromatic?

Author keywords

Aromaticity; Cyclopentadienes; Density functional calculations; NICS scan; Stabilization

Indexed keywords

AROMATIC HYDROCARBONS; DIAMAGNETISM; ELECTRIC CURRENTS; PARAMAGNETISM;

EID: 33645313206     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200501090     Document Type: Article
Times cited : (101)

References (43)
  • 1
    • 32144434172 scopus 로고    scopus 로고
    • ASAP, DOI: 10.1021/jo051746o
    • A. Stanger, J. Org. Chem. 2005, ASAP, DOI: 10.1021/jo051746o.
    • (2005) J. Org. Chem.
    • Stanger, A.1
  • 3
    • 33645284511 scopus 로고    scopus 로고
    • note
    • The probe for the NICS calculations is a ghost atom which is called "bq" in the Gaussian package after Banquo, the ghost that hunts Macbeth. This naming will be used throughout the paper.
  • 5
    • 3142716769 scopus 로고    scopus 로고
    • For support of the RCM model (and criticism of the above-mentioned paper), see: b) R. G. Viglione, R. Zanasi, Org. Lett. 2004, 6, 2265.
    • (2004) Org. Lett. , vol.6 , pp. 2265
    • Viglione, R.G.1    Zanasi, R.2
  • 6
    • 33645327216 scopus 로고    scopus 로고
    • Chemical shifts taken from the SDBS (Spectral Database for Organic Compounds)
    • Chemical shifts taken from the SDBS (Spectral Database for Organic Compounds): http://www.aist.go.jp/RIODB/SDBS/menu-e.html.
  • 10
    • 33645291587 scopus 로고    scopus 로고
    • note
    • NICS(1) is the Isotropic nucleus-independent chemical-shift value (ppm) which is calculated 1 Å above the center of the molecular plane.
  • 12
    • 33645321933 scopus 로고    scopus 로고
    • note
    • 3Sn, δ = 6.50 ppm;
  • 15
    • 33645316172 scopus 로고    scopus 로고
    • note
    • 3, δ = 5.94 ppm;
  • 16
    • 33645286578 scopus 로고    scopus 로고
    • note
    • 2SiOMe, δ = 6.5 ppm;
  • 18
    • 33645280417 scopus 로고    scopus 로고
    • note
    • 3Ge, δ = 6.35 ppm;
  • 19
    • 33645319542 scopus 로고    scopus 로고
    • note
    • 3Si, δ = 6.65 ppm;
  • 21
    • 33645300161 scopus 로고    scopus 로고
    • note
    • 3Si, δ = 6.3 ppm;
  • 23
    • 6344261884 scopus 로고    scopus 로고
    • Recently, there have been reports about the NICS being inconsistent with other indices of aromaticity. See, for example: a) J. Poater, M. Solá, R. G. Viglione, R. Zanasi, J. Org. Chem. 2004, 69, 7537;
    • (2004) J. Org. Chem. , vol.69 , pp. 7537
    • Poater, J.1    Solá, M.2    Viglione, R.G.3    Zanasi, R.4
  • 27
    • 33645276093 scopus 로고    scopus 로고
    • See also ref. [1]
    • e) See also ref. [1].
  • 29
    • 33645318518 scopus 로고    scopus 로고
    • note
    • imag = 0).
  • 32
    • 33645300446 scopus 로고    scopus 로고
    • note
    • [9] that could be studied within the same theoretical level.
  • 35
    • 33645284274 scopus 로고    scopus 로고
    • See, for example: a ref. [2]
    • See, for example: a) ref. [2].
  • 36
    • 33645305221 scopus 로고    scopus 로고
    • For statements concerning NICS(1) as a measure of aromaticity and antiaromaticity see, for example, ref. [4a]
    • b) For statements concerning NICS(1) as a measure of aromaticity and antiaromaticity see, for example, ref. [4a].
  • 37
    • 33645302447 scopus 로고    scopus 로고
    • note
    • The NICS scan of 4 is not indicative because the bq probe feels the effect of the hydrogen atoms of the trimethylsilyl groups. A similar effect (which, however, is remote enough and thus does not interfere with the shape close to the minima) can be observed in 3.
  • 43
    • 33645327766 scopus 로고    scopus 로고
    • note
    • Please note that there are strong currents induced in the lone pairs of fluorine which, however, are isotropic.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.