New insights into the geometry of resorc[4]arenes: Solvent-mediated supramolecular conformational and chiroptical control

Schiel C, Hembury GA, Borovkov VV, Klaes M, Agena C, Wada T, Grimme S, Inoue Y, Mattay J (2006)
The Journal of Organic Chemistry 71(3): 976-982.

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Zeitschriftenaufsatz | Veröffentlicht | Englisch
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Abstract / Bemerkung
The conformations of inherently chiral resorc[4]arenes were studied by circular dichroism (CD) spectroscopy. Whereas in aprotic solvents the crown conformation (C-4) is preferred, protic solvents favor the boat conformation (C-2). As a result of electronic coupling of the lowest L-b state of the resorcinol unit in the resorc[4]arene, the CD spectra show a strong dependence on the conformation of the macrocycle. For the first time the solvent dependence of the CD spectra was qualitatively analyzed and simulated by using theoretical methods. We have thus demonstrated not only that the conformation of the calixarene is dramatically manipulated by the solvent but also that the joint use of chiroptical measurements and theoretical calculations is a powerful and versatile tool for elucidating structural variations in supramolecular chemistry.
Erscheinungsjahr
Zeitschriftentitel
The Journal of Organic Chemistry
Band
71
Zeitschriftennummer
3
Seite
976-982
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Schiel C, Hembury GA, Borovkov VV, et al. New insights into the geometry of resorc[4]arenes: Solvent-mediated supramolecular conformational and chiroptical control. The Journal of Organic Chemistry. 2006;71(3):976-982.
Schiel, C., Hembury, G. A., Borovkov, V. V., Klaes, M., Agena, C., Wada, T., Grimme, S., et al. (2006). New insights into the geometry of resorc[4]arenes: Solvent-mediated supramolecular conformational and chiroptical control. The Journal of Organic Chemistry, 71(3), 976-982. doi:10.1021/jo0518654
Schiel, C., Hembury, G. A., Borovkov, V. V., Klaes, M., Agena, C., Wada, T., Grimme, S., Inoue, Y., and Mattay, J. (2006). New insights into the geometry of resorc[4]arenes: Solvent-mediated supramolecular conformational and chiroptical control. The Journal of Organic Chemistry 71, 976-982.
Schiel, C., et al., 2006. New insights into the geometry of resorc[4]arenes: Solvent-mediated supramolecular conformational and chiroptical control. The Journal of Organic Chemistry, 71(3), p 976-982.
C. Schiel, et al., “New insights into the geometry of resorc[4]arenes: Solvent-mediated supramolecular conformational and chiroptical control”, The Journal of Organic Chemistry, vol. 71, 2006, pp. 976-982.
Schiel, C., Hembury, G.A., Borovkov, V.V., Klaes, M., Agena, C., Wada, T., Grimme, S., Inoue, Y., Mattay, J.: New insights into the geometry of resorc[4]arenes: Solvent-mediated supramolecular conformational and chiroptical control. The Journal of Organic Chemistry. 71, 976-982 (2006).
Schiel, Christian, Hembury, Guy A., Borovkov, Victor V., Klaes, Michael, Agena, Ceno, Wada, Takehiko, Grimme, Stefan, Inoue, Yoshihisa, and Mattay, Jochen. “New insights into the geometry of resorc[4]arenes: Solvent-mediated supramolecular conformational and chiroptical control”. The Journal of Organic Chemistry 71.3 (2006): 976-982.

3 Zitationen in Europe PMC

Daten bereitgestellt von Europe PubMed Central.

Cyclochiral resorcin[4]arenes as effective enantioselectors in the gas phase.
Fraschetti C, Letzel MC, Paletta M, Mattay J, Speranza M, Filippi A, Aschi M, Rozhenko AB., J Mass Spectrom 47(1), 2012
PMID: 22282092
Dimeric nanocapsule induces conformational change.
Maerz AK, Thomas HM, Power NP, Deakyne CA, Atwood JL., Chem Commun (Camb) 46(8), 2010
PMID: 20449261

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