NDLI: Host–guest complexation of antioxidative caffeic and ferulic acid amides with a functionalized cyclophane

Content Provider	Springer Nature Link
Author	Virués, Claudia Domínguez, Zaira Salas, Magali Navarro, Rosa Elena Velázquez, Enrique F. Cruz, Samuel Hernández, Javier Iue, Motomichi
Copyright Year	2012
Abstract	Host−guest complexation has been studied by $^{1}$H NMR on the benzyl and phenethyl amides of ferulic and caffeic acids as the guests in chloroform and acetonitrile; the counter host is a cyclophane which integrates four phenylene rings, amino and amide groups in the macrocyclic framework and bears four pendant methyl acetate ester arms. CAPE, one of the best known natural antioxidants, also has been studied for comparison. Among the guests studied, ferulic acid benzyl amide shows NMR shifts due to the formation of a host−guest complex in chloroform. The complexation occurs in two steps with the formation constants K $_{1}$ = [HG]/[H][G] = 6 M$^{−1}$ and β $_{2}$ = [HG$_{2}$]/[H][G]$^{2}$ = 87 M$^{−2}$. Two guest molecules are bound on the surface of the macrocyclic framework of a host molecule by two hydrogen bonds, NH(host amide)···O=C(guest amide) and C=O(host ester)···HO(guest phenol). The latter hydrogen bond may protect the bioactive site, i.e., phenol OH, of guest molecules captured in the complex against undesirable oxidation. This feature is observed only for ferulic acid benzyl amide in chloroform; the cyclophane ester interacts with this amide, distinctively from the other hydroxycinnamic acid derivatives.
Starting Page	407
Ending Page	413
Page Count	7
File Format	PDF
ISSN	09230750
Journal	Journal of Inclusion Phenomena and Macrocyclic Chemistry
Volume Number	74
Issue Number	1-4
e-ISSN	15731111
Language	English
Publisher	Springer Netherlands
Publisher Date	2012-03-17
Publisher Place	Dordrecht
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Antioxidants Caffeic acid Ferulic acid Hydroxycinnamic acid derivatives Cyclophanes Host−guest complexes Food Science Crystallography Organic Chemistry
Content Type	Text
Resource Type	Article
Subject	Chemistry Condensed Matter Physics Food Science

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