title: Noncovalent complexation of glucosylthioureidocalix[4]arenes with carboxylates and their gas-phase characteristics: an ESI-FTICR mass spectrometric study.
abstract: The noncovalent complexation of three glucosylcalix[4]arenes (1-3) towards 23 mono- and dicarboxylic acid anions were studied by ESI-FTICR mass spectrometry. Competitive complexation, collision-induced dissociation and gas-phase H/D-exchange experiments were performed to obtain information on selectivity of calixarenes towards carboxylates and characteristics of their complexes. The flexibility and number of glucose units of the host and the spatial disposition of the hydrogen bonding groups on the carboxylate guests were found to affect the selectivity of complexation strongly. The glucosylcalixarenes exhibited particular selectivity for dicarboxylic acid anions incorporating π-systems, and clear isomeric selectivity was observed for isophthalic among phthalic acid anions and for fumaric acid over maleic acid anion.
authors.affiliation: Department of Chemistry, University of Eastern Finland, P.O. Box 111, 80101 Joensuu, Finland.
authors.forename: Mika
authors.initials: M
authors.lastname: Torvinen
authors.forename: Elina
authors.initials: E
authors.lastname: Kalenius
authors.forename: Francesco
authors.initials: F
authors.lastname: Sansone
authors.forename: Alessandro
authors.initials: A
authors.lastname: Casnati
authors.forename: Janne
authors.initials: J
authors.lastname: Jänis
mesh_terms: D047250:Calixarenes / Q000737:chemistry*; D002264:Carboxylic Acids / Q000737:chemistry*; D041961:Deuterium Exchange Measurement / Q000379:methods; D005947:Glucose / Q000737:chemistry*; D006001:Glycoconjugates / Q000737:chemistry*; D021241:Spectrometry, Mass, Electrospray Ionization / Q000379:methods; D013890:Thiourea / Q000737:chemistry*
chemical_list: D002264:Carboxylic Acids; D006001:Glycoconjugates; D047250:Calixarenes; D013890:Thiourea; D005947:Glucose