PMID: 11902859Mar 21, 2002Paper

Water-stabilized cavitands

Journal of the American Chemical Society
Adel Rafai FarJulius Rebek

Abstract

Tetrabenzimidazole cavitands 4 were prepared by condensation of ortho esters with octaamino cavitand 3 in 70-80% yield. Molecular modeling predicted that no intramolecular hydrogen bonds are possible between the imidazole fragments in the vase conformation of 4. Instead, this conformation provides four perfect binding sites for hydroxyl-containing molecules through an N-H---O-H---N pattern. Such interactions provide the means for sealing the cavitand's cavity. Accordingly, dry compounds 4 are not soluble in dry CDCl3 but readily dissolve upon addition of small amounts of alcohols or by saturation of the solution with water. 1H NMR spectroscopy revealed that in these solutions molecules 4 adopt a vase conformation while 1D GOESY experiments revealed their monomeric nature. In water-saturated CDCl3, these cavitands 4 form kinetically stable 1:1 inclusion complexes with tetramethylphosphonium bromide and triethylammonium chloride in which the cation is incorporated into the pi-basic cavity. Thus, cavitands 4 are a novel class of open-ended molecular containers capable of the formation of highly kinetically stable complexes upon assistance by hydrogen-bonding water molecules.

References

Nov 10, 2000·Chemistry : a European Journal·T HainoJ Rebek
Nov 25, 2000·Angewandte Chemie·B Twamley, P P Power
Jan 1, 1999·Angewandte Chemie·P L HollandW B Tolman

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Citations

Oct 7, 2010·Organic Letters·Eric Busseron, Julius Rebek
Jul 29, 2008·Organic Letters·Agustí LledóJulius Rebek
Dec 8, 2005·Chemical Communications : Chem Comm·Clemens H HaasJulius Rebek
Apr 13, 2010·Chemical Communications : Chem Comm·Yuji KuboTakashi Fujihara
May 22, 2010·Chemical Communications : Chem Comm·Enrique BotanaJavier de Mendoza
Oct 14, 2010·Chemical Communications : Chem Comm·Agustí Lledó, Julius Rebek
Jun 6, 2006·Proceedings of the National Academy of Sciences of the United States of America·Dariush AjamiJulius Rebek
Jul 27, 2005·Proceedings of the National Academy of Sciences of the United States of America·Byron W Purse, Julius Rebek
Aug 19, 2014·Langmuir : the ACS Journal of Surfaces and Colloids·Yoo-Jin GhangRichard J Hooley
Sep 9, 2015·Chemical Reviews·Sundus Erbas-CakmakAlina L Nussbaumer
Nov 26, 2013·Chemical Communications : Chem Comm·A AsadiJ Rebek
Dec 22, 2016·Angewandte Chemie·Oliver DumeleFrançois Diederich
Sep 27, 2006·Angewandte Chemie·Kent A NielsenJan O Jeppesen
Sep 26, 2014·Chemical Communications : Chem Comm·V HaridasAshutosh Shandilya
May 28, 2015·Angewandte Chemie·Oliver DumeleFrançois Diederich
May 30, 2017·Chemical Science·Yang LiuRichard J Hooley
Jun 23, 2015·Chemistry : a European Journal·Sheila Ruiz-BotellaEduardo Peris
Oct 21, 2016·Chemistry : a European Journal·Sheila Ruiz-BotellaEduardo Peris
Jan 28, 2012·Organic & Biomolecular Chemistry·Pedro MolinaFrancisco Otón
Feb 26, 2005·The Journal of Organic Chemistry·Ivy Philip, Angel E Kaifer
May 13, 2009·Organic Letters·Seiji KamiokaTakayuki Doi
Sep 28, 2017·Analytical Chemistry·Yang LiuRichard J Hooley
Feb 17, 2018·Journal of the American Chemical Society·Cornelius GroppFrançois Diederich
Dec 14, 2011·Langmuir : the ACS Journal of Surfaces and Colloids·Ying LiuRichard J Hooley
Dec 18, 2020·Organic Letters·Edison CastroRaúl Hernández Sánchez
Nov 21, 2002·Journal of the American Chemical Society·Pablo BallesterJulius Rebek
Nov 19, 2004·Organic Letters·Heung-Jin ChoiKyungsoo Paek

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