Conformational equilibrium in supramolecular chemistry: Dibutyltriuret case

Beilstein Journal of Organic Chemistry

Erkki Kolehmainen¹  Borys Ośmiałowski²  Marek Pietrzak²  Małgorzata Kaczorowska²  Karina Mroczyńska²  Ireneusz Grubecki² 

[1] Department of Chemistry, University of Jyväskylä, P.O. Box 35, FI-40014, Jyväskylä, Finland;Faculty of Chemical Technology and Engineering, UTP University of Science and Technology, Seminaryjna 3, PL-85326 Bydgoszcz, Poland;

关键词: association;    hydrogen bonding;    NMR;    rotamerism;    supramolecular chemistry;   

DOI  :  10.3762/bjoc.11.227

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown