Conformational changes in cryptophane having C1-symmetry studied by vibrational circular dichroism

The Journal of Physical Chemistry. a
Thierry BrotinThierry Buffeteau

Abstract

Vibrational circular dichroism (VCD) measurements and density functional theory (DFT) calculations were used to obtain the absolute configuration of a cryptophane molecule having C1-symmetry (labeled cryptophane-H). This molecule exhibits chiroptical properties different from those published for cryptophane-A having D3-symmetry [Brotin et al. J. Am. Chem. Soc. 2006, 128, 5533-5540]. In particular, we have shown that the conformation of the aliphatic linkers is very dependent on the solvent used and its ability to enter (CDCl3 solution) or not (C2D2Cl4 solution) in the cryptophane cavity. Calculations performed at the DFT (B3PW91/6-31G*) level establish, besides the absolute configuration, the preferential anti and gauche conformations of the aliphatic linkers of the chloroform@cryptophane-H complex and the empty cryptophane-H molecule, respectively. Polarimetric measurements performed in several solvents reflect also the change of conformation of the bridges upon guest encapsulation.

References

Jul 18, 2002·Chemical Communications : Chem Comm·Magali DarzacJean-Pierre Dutasta
Aug 13, 2004·Biopolymers·Feng WangPrasad L Polavarapu
Nov 19, 2004·Journal of the American Chemical Society·Megan M SpenceAlexander Pines
Apr 20, 2006·Journal of the American Chemical Society·Thierry BrotinThierry Buffeteau
Jun 21, 2006·Chemical Communications : Chem Comm·Thierry BuffeteauIvan Huc
May 18, 2007·The Journal of Physical Chemistry. a·Laurent DucasseThierry Buffeteau
Dec 7, 2007·The Journal of Organic Chemistry·Dominique CavagnatThierry Brotin

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Citations

Jan 27, 2011·Nature Communications·Olena TaratulaIvan J Dmochowski
Jun 14, 2012·The Journal of Physical Chemistry. B·Zoltan TakacsJozef Kowalewski
Jun 11, 2009·Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry·Julien GuthmullerBenoît Champagne
Nov 8, 2012·Magnetic Resonance in Chemistry : MRC·Z TakacsJ-P Dutasta
Jul 1, 2010·Magnetic Resonance in Chemistry : MRC·Z TakacsJ P Dutasta
Jun 20, 2015·The Journal of Physical Chemistry. B·Thierry BrotinThierry Buffeteau
Dec 24, 2011·The Journal of Organic Chemistry·Thierry BrotinThierry Buffeteau
Apr 29, 2014·The Journal of Physical Chemistry. B·Nicolas DaugeyThierry Buffeteau
Apr 8, 2011·The Journal of Organic Chemistry·Aude BouchetThierry Buffeteau
Jun 5, 2013·The Journal of Organic Chemistry·Thierry BrotinThierry Buffeteau
Jun 4, 2014·The Journal of Organic Chemistry·Thierry BrotinThierry Buffeteau
Aug 4, 2012·The Journal of Physical Chemistry. B·Thierry BrotinThierry Buffeteau
May 28, 2019·Chirality·Orsola BaydounThierry Brotin
Jan 28, 2011·The Journal of Organic Chemistry·Aude BouchetThierry Buffeteau
Dec 16, 2016·The Journal of Physical Chemistry. B·Delphine PitratThierry Brotin
Sep 1, 2021·Chirality·Orsola BaydounThierry Brotin

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