Naslov
Recognition of N-Alkyl- and N-Aryl-Acetamides by N-Alkyl Ammonium Resorcinarene Chlorides

Autori
Kodiah Beyeh, Ngong ; Ala-Korpi, Altti ; Cetina, Mario ; Valkonen, Arto ; Rissanen, Kari

Izvornik
Chemistry : a European journal (0947-6539) 20 (2014), 46; 15144-15150

Vrsta, podvrsta i kategorija rada
Radovi u časopisima, članak, znanstveni

Ključne riječi
resorcinarenes; NMR titration; amides; host-guest complexes; X-ray crystallography

Sažetak
N-alkyl ammonium resorcinarene chlorides are stabilized by an intricate array of intra- and intermolecular hydrogen bonds leading to cavitand-like structures. Depending on the upper rim substituents, self-inclusion was observed in solution and in the solid state. The self-inclusion can be disrupted at higher temperatures while in the presence of small guests, the self-included dimers spontaneously reorganize to 1:1 host-guest complexes. These host compounds show interesting ability in binding a series of N-alkyl acetamides guests through intermolecular hydrogen bonds involving the carbonyl oxygen (–C=O) and the amide (–NH) groups of the guests, the chloride anions (Cl-) and ammonium (–NH2+-) cations of the hosts and also through CH∙∙∙π interactions between the hosts and guests. The self-included and host guest complexes were studied by single crystal X-ray diffraction, NMR titration and mass spectrometric studies.

Izvorni jezik
Engleski

Znanstvena područja
Kemija

POVEZANOST RADA