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Article Dans Une Revue Magnetic Resonance in Chemistry Année : 2013

Host-guest complexes between cryptophane-C and chloromethanes revisited

Z. Takacs
  • Fonction : Auteur
M. Soltesova
  • Fonction : Auteur
J. Kowalewski
  • Fonction : Auteur
Jérôme Lang
Thierry Brotin
J.-P. Dutasta

Résumé

Cryptophane-C is composed of two nonequivalent cyclotribenzylene caps, one of which contains methoxy group substituents on the phenyl rings. The two caps are connected by three OCH2CH2O linkers in an anti arrangement. Host–guest complexes of cryptophane-C with dichloromethane and chloroform in solution were investigated in detail by nuclear magnetic resonance techniques and density functional theory (DFT) calculations. Variable temperature proton and carbon-13 spectra show a variety of dynamic processes, such as guest exchange and host conformational transitions. The guest exchange was studied quantitatively by exchange spectroscopy measurements or by line-shape analysis. The conformational preferences of the guest-containing host were interpreted through cross-relaxation measurements, providing evidence of the gauche+2 and gauche−2 conformations of the linkers. In addition, the mobility of the chloroform guest inside the cavity was studied by carbon-13 relaxation experiments. Combining different types of evidence led to a detailed picture of molecular recognition, interpreted in terms of conformational selection. Copyright © 2012 John Wiley & Sons, Ltd.

Dates et versions

hal-01117199 , version 1 (16-02-2015)

Identifiants

Citer

Z. Takacs, M. Soltesova, J. Kowalewski, Jérôme Lang, Thierry Brotin, et al.. Host-guest complexes between cryptophane-C and chloromethanes revisited. Magnetic Resonance in Chemistry, 2013, 51 (1), pp.19-31. ⟨10.1002/mrc.3898⟩. ⟨hal-01117199⟩
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