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Volumn 74, Issue 3, 2009, Pages 1345-1348

Structure, stereodynamics and absolute configuration of the atropisomers of hindered arylanthraquinones

Author keywords

[No Author keywords available]

Indexed keywords

ABSOLUTE CONFIGURATIONS; ATROPISOMERS; ENANTIOSELECTIVE HPLC; NAPHTHYL GROUPS; STEREODYNAMICS; X- RAY DIFFRACTIONS;

EID: 64549117421     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo802383s     Document Type: Article
Times cited : (17)

References (43)
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    • Frisch, M. J, Trucks, G. W, Schlegel, H. B, Scuseria, G. E, Robb, M. A, Cheeseman, J. R, Montgomery, J. A, Jr, Vreven, T, Kudin, K. N, Burant, J. C, Millam, J. M, Iyengar, S. S, Tomasi, J, Barone, V, Mennucci, B, Cossi, M, Scalmani, G, Rega, N, Petersson, G. A, Nakatsuji, H, Hada, M, Ehara, M, Toyota, K, Fukuda, R, Hasegawa, J, Ishida, M, Nakajima, T, Honda, Y, Kitao, O, Nakai, H, Klene, M, Li, X, Knox, J. E, Hratchian, H. P, Cross, J. B, Bakken, V, Adamo, C, Jaramillo, J, Gomperts, R, Stratmann, R. E, Yazyev, O, Austin, A. J, Cammi, R, Pomelli, C, Ochterski, J. W, Ayala, P. Y, Morokuma, K, Voth, G. A, Salvador, P, Dannenberg, J. J, Zakrzewski, V. G, Dapprich, S, Daniels, A. D, Strain, M. C, Farkas, O, Malick, D. K, Rabuck, A. D, Raghavachari, K, Foresman, J. B, Ortiz, J. V, Cui, Q, Baboul, A. G, Clifford, S, Cioslowski, J, Stefanov, B. B, Liu, G, Liashenko, A, Piskorz, P, Komaromi, I, Martin, R. L, Fox, D. J, Keit
    • Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Montgomery, J. A., Jr.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Iyengar, S. S.; Tomasi, J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji, H.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.; Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A. G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.; Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.; Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J. A. Gaussian 03, Revision E.01; Gaussian, Inc., Wallingford, CT, 2004.
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    • -1)so that the corresponding pathway is not expected to take place.
    • -1)so that the corresponding pathway is not expected to take place.
  • 24
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    • -1/6, according to: Claridge, T. D. W. High-Resolution NMR Techniques in Organic Chemistry; Pergamon Press: Oxford, 1999; p 303.
    • -1/6, according to: Claridge, T. D. W. High-Resolution NMR Techniques in Organic Chemistry; Pergamon Press: Oxford, 1999; p 303.
  • 25
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    • This attribution agrees with the trend of the 1H shift of the corresponding methyl groups, that of 1a (2.02 ppm) being at lower field with respect to that of 1b 1.68 ppm, The latter should thus correspond to the anti structure since its methyl groups lie in a position where they experience the upfield shift displacement due to the aromatic ring currents; see: Jackman, L. M, Sternhell, S. Applications of NMR Spectroscopy in Organic Chemistry, 2nd ed, Pergamon Press: Oxford, 1969; p 95. Jennings, W. B, Farrell, B. M, Malone, J. F Acc. Chem. Res. 2001, 34, 885-894
    • 1H shift of the corresponding methyl groups, that of 1a (2.02 ppm) being at lower field with respect to that of 1b (1.68 ppm). The latter should thus correspond to the anti structure since its methyl groups lie in a position where they experience the upfield shift displacement due to the aromatic ring currents; see: Jackman, L. M.; Sternhell, S. Applications of NMR Spectroscopy in Organic Chemistry, 2nd ed.; Pergamon Press: Oxford, 1969; p 95. Jennings, W. B.; Farrell, B. M.; Malone, J. F Acc. Chem. Res. 2001, 34, 885-894.
  • 26
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    • 9 predict an upfield methyl shift for the anti (1.71 ppm) with respect to the syn 2.16 ppm, in agreement with the observed trend
    • 9 predict an upfield methyl shift for the anti (1.71 ppm) with respect to the syn (2.16 ppm), in agreement with the observed trend.
    • (2003) Angew. Chem. Int. Ed , vol.42 , pp. 3340-3363
    • Wuthrich, K.1
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    • For the assignments made by TDDFT-CD calculations, see: Diedrich, C; Grimme, S. J.Phys. Chem. A 2003, 107, 2524. Stephens, P. J.; McCann, D. M.; Butkus, E.; Stoncius, S.; Cheeseman, J. R.; Frisch, M. J J. Org. Chem. 2004, 69, 1948.
    • For the assignments made by TDDFT-CD calculations, see: Diedrich, C; Grimme, S. J.Phys. Chem. A 2003, 107, 2524. Stephens, P. J.; McCann, D. M.; Butkus, E.; Stoncius, S.; Cheeseman, J. R.; Frisch, M. J J. Org. Chem. 2004, 69, 1948.
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    • It has to be pointed out that the experimental interconversion is accomplished via the rotation of either of the two naphthalene rings, whereas the computed value was obtained assuming the rotation of only one ring. Thus, for an appropriate comparison the experimental rate constant should be divided by 2 see, for instance: Lunazzi, L, Mazzanti, A, Minzoni, M. J. Org. Chem. 2007, 72, 2501-2507
    • It has to be pointed out that the experimental interconversion is accomplished via the rotation of either of the two naphthalene rings, whereas the computed value was obtained assuming the rotation of only one ring. Thus, for an appropriate comparison the experimental rate constant should be divided by 2 (see, for instance: Lunazzi, L.; Mazzanti, A.; Minzoni, M. J. Org. Chem. 2007, 72, 2501-2507.
  • 38
    • 64549132918 scopus 로고    scopus 로고
    • Accordingly, the value of the experimental barrier which actually corresponds to the rotation of a single ring becomes slightly higher, i.e, 35.9 kcal mol-1
    • -1.
  • 39
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    • The presence of two substituents might be responsible for the observed interconversion barrier as a consequence of a possible buttressing effect
    • The presence of two substituents might be responsible for the observed interconversion barrier as a consequence of a possible buttressing effect.
  • 40
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    • 2 solution when using a 37:1 molar excess of enantiopure (R)-(-)-2, 2, 2-trifluoro-1-(9-anthryl)ethanol; see: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387.
    • 2 solution when using a 37:1 molar excess of enantiopure (R)-(-)-2, 2, 2-trifluoro-1-(9-anthryl)ethanol; see: Pirkle, W. H.; Sikkenga, D. L.; Pavlin, M. S. J. Org. Chem. 1977, 42, 384-387.
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    • Prepared according to: Thompson, W. J.; Gaudino, J. J. Org. Chem. 1984, 49, 5237.
    • Prepared according to: Thompson, W. J.; Gaudino, J. J. Org. Chem. 1984, 49, 5237.
  • 42
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    • Available at
    • (a) GaussSum 2.1.3,2007. Available at http://gausssum.sf.net.
    • (2007) GaussSum 2.1.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.