DFT study the interaction of beta-cyclodextrin with benzyl azide and phenyl acetylene in synthesis of 1,2,3-triazoles

摘要

The phenyl acetylene and benzyl azide cycloaddition reaction in water in the presence of -cyclodextrin (-CD) as a phase transfer catalyst (PTC) can get a better yield in a shorter time. The interaction between -CD and phenyl acetylene or benzyl azide plays an important role in this reaction. This paper studies the complexes of -CD with phenyl acetylene and benzyl azide using density functional theory (DFT) method. In order to find out the orientations of guests in the cavity of -CD, binding energy and deformation energy are investigated, and the calculated results are confirmed by H-1 nuclear magnetic resonance ((HNMR)-H-1). The data from single point energy indicate that the inclusion complexes can improve the solubilities of phenyl acetylene and benzyl azide in water. The C-13 and N-15 spectra show that the most obvious variation concentrates on C-6 and C-8 of phenyl acetylene and N-15 of benzyl azide in complexes. Mulliken charge and frontier orbital are employed for revealing the charge distribution. The effect of -CD is discussed in terms of the calculated parameters. Copyright (c) 2014 John Wiley & Sons, Ltd.