Circular dichroism spectra (350-185 nm) of a new series of 4- substituted [2.2]paracyclophanes: A quantitative analysis within the devoe polarizability model

Tetrahedron Asymmetry

Volumn 9, Issue 1, 1998, Pages 55-62

  Rosini, Carlo ^a   Ruzziconi, Renzo ^a   Superchi, Stefano ^a   Fringuelli, Francesco ^b   Piermatti, Oriana ^b  

^a UNIVERSITY OF BASILICATA   (Italy)

^b UNIVERSITY OF PERUGIA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

PARACYCLOPHANE DERIVATIVE;

ARTICLE; CALCULATION; CHIRALITY; CIRCULAR DICHROISM; DIPOLE; MODEL; PRIORITY JOURNAL;

EID: 0032535961     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(97)00522-3     Document Type: Article

References (25)

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3. Falk, H.; Reich-Rohrwig, P.; Schlögl, K. Tetrahedron 1970, 26, 511.
4. Tochtermann, W.; Vagt, U.; Snatzke, G., Chem. Ber. 1985, 118, 1996.
5. Several relevant papers recently appeared by F. Vögtle et al. where the CD spectra of other paracyclophanes have been described. See, for instance, Pischel, I.; Nieger, M.; Archut, A.; Vögtle, F. Tetrahedron 1996, 52, 10043.
6. Cram, D. J.; Allinger, N. L. J. Am. Chem. Soc. 1955, 77, 6289.
7. (a) Mason, S. F. "Molecular Optical Activity and the Chiral Discriminations", Cambridge University Press, Cambridge, 1982;
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9. (c) Nakanishi, K.; Berova, N. in "Circular Dichroism: Principles and Applications" Nakanishi, K.; Berova, N.; Woody, R. W., Eds., VCH Publishers, New York, 1994, chap. 13, p. 361;
10. (d) A different approach, alternative to the chirality rules has been recently introduced. See: Rodger, A.; Norden, B. "Circular Dichroism and Linear Dichroism" Oxford University Press, Oxford, 1997.
11. Cipiciani, A.; Fringuelli, F.; Mancini, V.; Piermatti, O.; Pizzo, F.; Ruzziconi, R. J. Org. Chem. 1997, 62, 3744.
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13. b.
14. b.
15. Murrel suggests a value of spectroscopic moment for I (+13) significantly lower than the original one (+21) of Platt (see Ref. 10). Murrel, J. N. "The Theory of Electronic Spectra of Organic Molecules" Methuen, London, 1963, p. 207.
16. max of the chromophore involved (See Ref. 7b and Heyn, M. P. J. Phys. Chem. 1975, 79, 2424).
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21. 12 is the point-dipole-point-dipole interaction term. This expression gives rise to a couplet-like feature if the absorption maxima of the chromophore 1 and 2 are near in frequency ("quasidegenerate" coupled oscillator system). DeVoe, H. J. Chem. Phys. 1964, 41, 393; ibidem 1965, 43, 3199. For some applications of these calculations to structural problems see: Rosini, C.; Salvadori, P.; Zandomeneghi, M. Tetrahedron: Asymmetry 1993, 4, 545.
22. 12 is the point-dipole-point-dipole interaction term. This expression gives rise to a couplet-like feature if the absorption maxima of the chromophore 1 and 2 are near in frequency ("quasidegenerate" coupled oscillator system). DeVoe, H. J. Chem. Phys. 1964, 41, 393; ibidem 1965, 43, 3199. For some applications of these calculations to structural problems see: Rosini, C.; Salvadori, P.; Zandomeneghi, M. Tetrahedron: Asymmetry 1993, 4, 545.
23. 12 is the point-dipole-point-dipole interaction term. This expression gives rise to a couplet-like feature if the absorption maxima of the chromophore 1 and 2 are near in frequency ("quasidegenerate" coupled oscillator system). DeVoe, H. J. Chem. Phys. 1964, 41, 393; ibidem 1965, 43, 3199. For some applications of these calculations to structural problems see: Rosini, C.; Salvadori, P.; Zandomeneghi, M. Tetrahedron: Asymmetry 1993, 4, 545.
24. Shingu, K.; Imajo, S.; Kuritani, H.; Hagishita, S.; Kuriyama, K. J. Am. Chem. Soc. 1983, 105, 6966.
25. a couplet.