Ternary complexation of benzoic acid with β-cyclodextrin and aminoacids. Experimental and theoretical studies

GARCIA MENDEZ, S; OTERO ESPINA, F.; LUZARDO ALVAREZ A; LONGHI, M.R.; QUEVEDO, M.A.; ZOPPI, A.

JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY

Springer

Año: 2016

0923-0750

-Cyclodextrin (b-CD) is a well-known host molecule used to prepare inclusion complexes. Considering that the three dimensional array of these complexesdepends on the inclusion mode of the guest molecule within the b-CD cavity, the development of methods to elucidate their structure is highly desired. The mainobjective of this work aimed to shed light on the structural and energetic features related to the effect of aminoacids (AA: glycine, valine, isoleucine, arginine and glutamic acid) as third components on the complexation of benzoicacid (BA) with b-CD. In addition, hippuric acid (HA), a structure resembling a BA-glycine conjugate, was included as a model molecule to compare the effect of glycine present as a chemical moiety covalently linked to the guestmolecule. Phase solubility analyses were performed to determine the relative binding affinities for binary (BA:b-CD and HA:bCD) and ternary (BA:b-CD:AA) complexes, obtaining the following results: BA:b-CD:AA[BA:b-CD:[HA:b-CD. As pa