Host guest complexes between cucurbit[n]urils and acetanilides having aminopropyl units
| Autor: | Hermenegildo García, Pedro Montes-Navajas, Mercedes Alvaro, Mireia Buaki-Sogo |
|---|---|
| Jazyk: | angličtina |
| Rok vydání: | 2013 |
| Předmět: |
Bridged-Ring Compounds
Models Molecular Stereochemistry Supramolecular chemistry Phenylenediamines Biomaterials chemistry.chemical_compound Colloid and Surface Chemistry Aniline QUIMICA ORGANICA Cucurbituril Polymer chemistry QUIMICA ANALITICA Solid supported complexes Acetanilide Alkyl Ions chemistry.chemical_classification Aniline Compounds Chemical shift Cucurbiturils Silicon Dioxide Surfaces Coatings and Films Electronic Optical and Magnetic Materials chemistry Spectrometry Mass Matrix-Assisted Laser Desorption-Ionization Acetanilides Titration Acetamide |
| Zdroj: | RiuNet. Repositorio Institucional de la Universitat Politécnica de Valéncia instname |
| Popis: | [EN] 2-(Propylamino)acetamide of aniline (1a), and bis-2-(propylamino)acetamide of ortho- (1b) and para-(1c) phenylenediamine form host-guest complexes with CB[6], CB[7] and CB[8] as evidenced by the variations in the H-1 NMR spectroscopy chemical shifts and observation in MALDI-TOF-MS and ESI-MS of ions at the corresponding mass. Binding constants for the 1:1 complexes were estimated from fluorescence titrations and were in the range 10(5)-10(6) M-1. Models based on molecular mechanics for these supramolecular complexes are provided. In spite of the different geometries arising from the ortho- or para-substitution, phenylenediamides form complexes of similar strength in which the hydrophobic alkyl chains are accommodated inside the host cavity. Formation of these host-guest complexes in the solid state was also achieved by modifying an aminopropyl silica with chloroacetanilides and preparing three silica having analogues of compounds 1a-c anchored to the solid particles. Titrations showed, however, that these solids can adsorb a large percentage of CBs by unselective interactions that are not related to the formation of inclusion complexes. Financial support by the Spanish Ministry of Science and Education (CTQ2012-36351 and CTQ2010-18671) is gratefully acknowledged. Mireia Buaki-Sogo also thanks the Spanish ministry for a post-graduate scholarship (CTQ2007-67805). |
| Databáze: | OpenAIRE |
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