A novel C3v-symmetrical calix[6](aza)cryptand with a remarkably high and selective affinity for small ammoniums.
Identifieur interne : 001341 ( Main/Exploration ); précédent : 001340; suivant : 001342A novel C3v-symmetrical calix[6](aza)cryptand with a remarkably high and selective affinity for small ammoniums.
Auteurs : Ulrich Darbost [France] ; Michel Giorgi ; Olivia Reinaud ; Ivan JabinSource :
- The Journal of organic chemistry [ 0022-3263 ] ; 2004.
Abstract
The three-step synthesis of a calix[6]arene capped with a TAC unit is presented. The novel C(3v)-symmetrical calix[6](aza)cryptand displayed an exceptionally high affinity for small ammoniums. NMR and X-ray diffraction analyses demonstrated the formation of endo-complexes. These complexes are stabilized thanks to (i) hydrogen bonding to both the aza cap and one phenolic unit of the calixarene and to (ii) cationic and CH-pi interactions between the ammonium and the aromatic walls of the host. Combined extraction and competitive binding experiments yielded the free energies of bindings DeltaG degrees in chloroform. The values are the highest ever obtained with a calixarene-type host. Calix[6]TAC displayed the best affinity for EtNH(3)(+). Comparison with other small ammoniums emphasizes the high selectivity of the recognition process.
DOI: 10.1021/jo035859o
PubMed: 15255711
Affiliations:
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The novel C(3v)-symmetrical calix[6](aza)cryptand displayed an exceptionally high affinity for small ammoniums. NMR and X-ray diffraction analyses demonstrated the formation of endo-complexes. These complexes are stabilized thanks to (i) hydrogen bonding to both the aza cap and one phenolic unit of the calixarene and to (ii) cationic and CH-pi interactions between the ammonium and the aromatic walls of the host. Combined extraction and competitive binding experiments yielded the free energies of bindings DeltaG degrees in chloroform. The values are the highest ever obtained with a calixarene-type host. Calix[6]TAC displayed the best affinity for EtNH(3)(+). Comparison with other small ammoniums emphasizes the high selectivity of the recognition process.</div></front></TEI><affiliations><list><country><li>France</li></country><region><li>Haute-Normandie</li><li>Région Normandie</li></region><settlement><li>Le Havre</li></settlement><orgName><li>Université du Havre</li></orgName></list><tree><noCountry><name sortKey="Giorgi, Michel" sort="Giorgi, Michel" uniqKey="Giorgi M" first="Michel" last="Giorgi">Michel Giorgi</name><name sortKey="Jabin, Ivan" sort="Jabin, Ivan" uniqKey="Jabin I" first="Ivan" last="Jabin">Ivan Jabin</name><name sortKey="Reinaud, Olivia" sort="Reinaud, Olivia" uniqKey="Reinaud O" first="Olivia" last="Reinaud">Olivia Reinaud</name></noCountry><country name="France"><region name="Région Normandie"><name sortKey="Darbost, Ulrich" sort="Darbost, Ulrich" uniqKey="Darbost U" first="Ulrich" last="Darbost">Ulrich Darbost</name></region></country></tree></affiliations></record>Pour manipuler ce document sous Unix (Dilib)
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