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Volumn 10, Issue 16, 2008, Pages 3421-3424

A new case of induced helical chirality in a bichromophoric system: Absolute configuration of transparent and flexible diols from the analysis of the electronic circular dichroism spectra of the corresponding di(1-naphthyl)ketals

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EID: 61349155467     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8012149     Document Type: Article
Times cited : (23)

References (25)
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    • (a) Nakanishi, K.; Berova, N. In Circular Dichroism: Principles and Applications; Nakanishi, K., Berova, N., Woody, R. W., Eds.; Wiley-VCH Publishers: New York, 2000; Chapter 12, pp 337-382.
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    • For a general discussion of the ab initio calculation of chiroptical properties: a
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    • Bultinck, P, de Winter, H, Langenaecker, W, Tollenaere, J, Eds, Dekker: NY, Chapter 26, pp
    • (f) Stephens, P. J. In Computational Medicinal Chemistry for Drug Discovery; Bultinck, P..; de Winter, H..; Langenaecker, W..; Tollenaere, J., Eds.; Dekker: NY, 2003; Chapter 26, pp 699-725.
    • (2003) Computational Medicinal Chemistry for Drug Discovery , pp. 699-725
    • Stephens, P.J.1
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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 C.02; Gaussian, Inc.: Wallingford, CT, 2004, http://www.gaussian.com/.
  • 25
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    • These populations have been obtained using the ΔG value of 0.18 kcal/mol, provided by the DFT calculations. With this energy difference, the populations become 66 and 33% at -133° C, in excellent agreement with some variable-temperature NMR measurements (see Figure 16 of Supporting Information). The same analysis provides an energy of activation for the P/M interconversion of about 9 kcal/mol (see Figure 16 of Supporting Information).
    • These populations have been obtained using the ΔG value of 0.18 kcal/mol, provided by the DFT calculations. With this energy difference, the populations become 66 and 33% at -133° C, in excellent agreement with some variable-temperature NMR measurements (see Figure 16 of Supporting Information). The same analysis provides an energy of activation for the P/M interconversion of about 9 kcal/mol (see Figure 16 of Supporting Information).


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