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Adamantane-bearing benzylamines and benzylamides: Novel building blocks for supramolecular systems with finely tuned binding properties towards β-cyclodextrin

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dc.title Adamantane-bearing benzylamines and benzylamides: Novel building blocks for supramolecular systems with finely tuned binding properties towards β-cyclodextrin en
dc.contributor.author Rouchal, Michal
dc.contributor.author Matelová, Alena
dc.contributor.author Pires de Carvalho, Fabiana
dc.contributor.author Bernat, Robert
dc.contributor.author Grbić, Dragan
dc.contributor.author Kuřitka, Ivo
dc.contributor.author Babinský, Martin
dc.contributor.author Marek, Radek
dc.contributor.author Čmelík, Richard
dc.contributor.author Vícha, Robert
dc.relation.ispartof Supramolecular Chemistry
dc.identifier.issn 1061-0278 Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued 2013
utb.relation.volume 25
utb.relation.issue 6
dc.citation.spage 349
dc.citation.epage 361
dc.type article
dc.language.iso en
dc.publisher Taylor and Francis en
dc.identifier.doi 10.1080/10610278.2013.783916
dc.relation.uri http://www.tandfonline.com/doi/abs/10.1080/10610278.2013.783916#.Uj_xoOR6nwM
dc.subject adamantane en
dc.subject amines en
dc.subject binding properties en
dc.subject cyclodextrins en
dc.subject host-guest systems en
dc.description.abstract Novel building blocks for the synthesis of supramolecular components based on adamantane-bearing benzylamines were prepared. The binding properties of these amines and the corresponding acetamides towards β-cyclodextrin (β-CD) were studied using mass spectrometry, NMR spectrometry, isothermal titration calorimetry and semi-empirical calculations. It was found that all of the examined guests predominantly formed 1:1 inclusion complexes in an enthalpy-driven manner with association constants of the order of 10 2-103 M-1. Stronger binding to the β-CD cavity was observed for guests with a longer spacer between the adamantane and benzene moieties and/or a 1,4-disubstituted benzene ring. © 2013 Taylor & Francis Group, LLC. en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1003373
utb.identifier.obdid 43869822
utb.identifier.scopus 2-s2.0-84879410402
utb.identifier.wok 000320020400005
utb.identifier.coden SCHEE
utb.source j-scopus
dc.date.accessioned 2013-07-27T14:55:31Z
dc.date.available 2013-07-27T14:55:31Z
utb.contributor.internalauthor Rouchal, Michal
utb.contributor.internalauthor Matelová, Alena
utb.contributor.internalauthor Pires de Carvalho, Fabiana
utb.contributor.internalauthor Kuřitka, Ivo
utb.contributor.internalauthor Vícha, Robert
utb.fulltext.affiliation Michal Rouchal a , Alena Matelová a , Fabiana Pires de Carvalho a , Robert Bernat a , Dragan Grbića , Ivo Kuřitka b , Martin Babinský c , Radek Marek c , Richard Čmelík d & Robert Vícha* a a Department of Chemistry , Faculty of Technology, Tomas Bata University in Zlín , Náměstí T. G. Masaryka 275, 762 72 , Zlín , Czech Republic b Polymer Centre, Faculty of Technology, Tomas Bata University in Zlín , Náměstí T. G.Masaryka 275, 762 72 , Zlín , Czech Republic c CEITEC – Central European Institute of Technology, Masaryk University , Kamenice 5, 62500 , Brno , Czech Republic d Institute of Analytical Chemistry, v. v. i., Academy of Sciences of the Czech Republic ,Veveří 97, 602 00 , Brno , Czech Republic *Corresponding author. Email: rvicha@ft.utb.cz
utb.fulltext.dates Received 19 October 2012 final version received 31 December 2012
utb.fulltext.sponsorship This work was supported by the Internal Founding Agency of Tomas Bata University in Zlín, project IGA/FT/2012/016 to A.M., M.R. and R.V., the project ‘CEITEC 2 Central European Institute of Technology’ (CZ.1.05/1.1.00/02.0068) from the European Regional Development Fund to R.M. and M.B. and institutional research plan RVO:68081715 to R.C.
utb.fulltext.projects IGA/FT/2012/016
utb.fulltext.projects CZ.1.05/1.1.00/02.0068
utb.fulltext.projects RVO:68081715
utb.fulltext.faculty Faculty of Technology
utb.fulltext.ou Department of Chemistry
utb.fulltext.ou Polymer Centre
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