Experimental and theoretical studies on the inclusion complexation of syringic acid with α-, β-, γ- and heptakis(2,6-di-O-methyl)-β-cyclodextrin

Intermolecular interactions of alpha-, beta-, gamma- and heptakis(2,6-di-O-methyl)-beta-cyclodextrin (CD) with syringic acid (Syr) in aqueous solution are investigated by fluorescence spectroscopy. The fluorescence intensity of Syr gradually increases with the addition of the CDs. The formation constants (K) of the host-guest inclusion complexes are determined using a nonlinear analysis. The association abilities of Syr with the CDs decrease in the order gamma ->beta ->alpha-approximate to DM beta-CD. Both the intrinsic binding abilities of the CDs and the structural effect of Syr are taken into consideration when comparing the K values. Based on the results of NMR experimental and theoretical PM3 calculations both in vacuo and in water, it is found that Syr stays near the wider rim of alpha-CD cavity. Both the number of substituted groups (NSG) in a guest and the molar volume ratio of the guest to host cavity (MVR) play an important role in forming the CD supramolecular complexes of a homologous series of phenol derivatives, such as 2-methoxylphenol (2-Mop), eugenol (Eug) and Syr, i.e., an appropriate NSG or MVR in an inclusion system, such as in 2-Mop-alpha-CD, Eug-beta-CD and Syr-gamma-CD systems, can maximize the intermolecular interaction between host and guest.