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Volumn 76, Issue 5, 2011, Pages 1487-1490

Structure, conformation, stereodynamics, and absolute configuration of the atropisomers of fluorenylidene derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATION; ATROPISOMERS; ELECTRONIC CIRCULAR DICHROISM; INTERCONVERSIONS; STEREODYNAMICS; VARIABLE-TEMPERATURE NMR;

EID: 79952150929     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo1023427     Document Type: Article
Times cited : (4)

References (36)
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    • In;, Ed.; Franz Deuticke: Leipzig,; pp -824.
    • Kuhn, R. Moleculare Asymmetrie. In Stereochemie; Freudenberg, K., Ed.; Franz Deuticke: Leipzig, 1933; pp 803 -824.
    • (1933) Stereochemie , pp. 803
    • Kuhn, R.1    Freudenberg, K.2
  • 8
    • 0002999412 scopus 로고
    • Recent Advances in Atropisomerism
    • In;;;, Eds.; Wiley Interscience: New York,; Vol., pp -76.
    • Oki, K. Recent Advances in Atropisomerism. In Topics in Stereochemistry; Allinger, N. L.; Eliel, E. E; Wilen, S. H, Eds.; Wiley Interscience: New York, 1983; Vol. 14, pp 1 -76.
    • (1983) Topics in Stereochemistry , vol.14 , pp. 1
    • Oki, K.1    Allinger, N.L.2    Eliel, E.E.3    Wilen, S.H.4
  • 14
    • 0038626673 scopus 로고    scopus 로고
    • B3LYP/6-31G(d) level., Revision E.01,; Gaussian, Inc., Wallingford, CT,. See the SI for the complete reference.
    • B3LYP/6-31G(d) level. Gaussian 03, Revision E.01, Frisch, M. J.; Gaussian, Inc., Wallingford, CT, 2004. See the SI for the complete reference.
    • (2004) Gaussian 03
    • Frisch, M.J.1
  • 15
    • 79952136059 scopus 로고    scopus 로고
    • -1) and the twisting angle of the double bond is about 50°.
    • -1) and the twisting angle of the double bond is about 50°.
  • 17
    • 43249092579 scopus 로고    scopus 로고
    • For a review on the use of X-ray Crystallography for the determination of the absolute configuration see:;,-690
    • For a review on the use of X-ray Crystallography for the determination of the absolute configuration see: Flack, H. D.; Bernardinelli, G. Chirality 2008, 20, 681-690
    • (2008) Chirality , vol.20 , pp. 681
    • Flack, H.D.1    Bernardinelli, G.2
  • 27
    • 70450206724 scopus 로고    scopus 로고
    • revision A.01;; Gaussian, Inc., Wallingford, CT.
    • Gaussian 09, Revision A.01; Frisch, M. J.; Gaussian, Inc., Wallingford, CT, 2009.
    • (2009) Gaussian 09
    • Frisch, M.J.1
  • 29
    • 2942665493 scopus 로고    scopus 로고
    • The rotational strengths were calculated in the length and velocity representations. The resulting values are very similar, and the errors due to basis set incompleteness are therefore very small, or negligible. See:;;;;,-7521
    • The rotational strengths were calculated in the length and velocity representations. The resulting values are very similar, and the errors due to basis set incompleteness are therefore very small, or negligible. See: Stephens, P. J.; McCann, D. M.; Devlin, F. J.; Cheeseman, J. R.; Frisch, M. J. J. Am. Chem. Soc. 2004, 126, 7514-7521
    • (2004) J. Am. Chem. Soc. , vol.126 , pp. 7514
    • Stephens, P.J.1    McCann, D.M.2    Devlin, F.J.3    Cheeseman, J.R.4    Frisch, M.J.5
  • 31
    • 28044451321 scopus 로고    scopus 로고
    • The use of more than one model enhances the reliability of the method, and it can serve as an evaluation of the amplitude of the possible error. See:;,-9834
    • The use of more than one model enhances the reliability of the method, and it can serve as an evaluation of the amplitude of the possible error. See: Check, C. E.; Gilbert, T. M. J. Org. Chem. 2005, 70, 9828-9834
    • (2005) J. Org. Chem. , vol.70 , pp. 9828
    • Check, C.E.1    Gilbert, T.M.2
  • 32
    • 79952135720 scopus 로고    scopus 로고
    • neither of the enantiomers of the major diastereisomer 3a yielded crystals suitable for a structural determination by X-ray diffraction.
    • Neither of the enantiomers of the major diastereisomer 3a yielded crystals suitable for a structural determination by X-ray diffraction.
  • 33
    • 79952168608 scopus 로고    scopus 로고
    • -1).
    • -1).
  • 34
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    • note
    • 2O in the NMR sample should lead to a partial (or total) deuteration of the CH and Me groups, a feature that it is not experimentally observed. This confirms that the energy barrier determined is that of the rotation of the aryl group.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.