title: Conformational equilibrium in supramolecular chemistry: Dibutyltriuret case.
abstract: The association of substituted benzoates and naphthyridine dianions was used to study the complexation of dibutyltriuret. The title molecule is the simplest molecule able to form two intramolecular hydrogen bonds. The naphthyridine salt was used to break two intramolecular hydrogen bonds at a time while with the use of substituted benzoates the systematic approach to study association was achieved. Both, titrations and variable temperature measurements shed the light on the importance of conformational equilibrium and its influence on association in solution. Moreover, the associates were observed by mass spectrometry. The DFT-based computations for complexes and single bond rotational barriers supports experimental data and helps understanding the properties of multiply hydrogen bonded complexes.
authors.affiliation: Faculty of Chemical Technology and Engineering, UTP University of Science and Technology, Seminaryjna 3, PL-85326 Bydgoszcz, Poland.
authors.forename: Karina
authors.initials: K
authors.lastname: Mroczyńska
authors.affiliation: Faculty of Chemical Technology and Engineering, UTP University of Science and Technology, Seminaryjna 3, PL-85326 Bydgoszcz, Poland.
authors.forename: Małgorzata
authors.initials: M
authors.lastname: Kaczorowska
authors.affiliation: Department of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014, Jyväskylä, Finland.
authors.forename: Erkki
authors.initials: E
authors.lastname: Kolehmainen
authors.affiliation: Faculty of Chemical Technology and Engineering, UTP University of Science and Technology, Seminaryjna 3, PL-85326 Bydgoszcz, Poland.
authors.forename: Ireneusz
authors.initials: I
authors.lastname: Grubecki
authors.affiliation: Faculty of Chemical Technology and Engineering, UTP University of Science and Technology, Seminaryjna 3, PL-85326 Bydgoszcz, Poland.
authors.forename: Marek
authors.initials: M
authors.lastname: Pietrzak
authors.affiliation: Faculty of Chemical Technology and Engineering, UTP University of Science and Technology, Seminaryjna 3, PL-85326 Bydgoszcz, Poland.
authors.forename: Borys
authors.initials: B
authors.lastname: Ośmiałowski
keywords: NMR; association; hydrogen bonding; rotamerism; supramolecular chemistry