Unusual Complex Formation and Chemical Reaction of Haloacetate Anion on the Exterior Surface of Cucurbit[6]uril in the Gas Phase |
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Authors: | Tae Su Choi Jae Yoon Ko Sung Woo Heo Young Ho Ko Kimoon Kim Hugh I Kim |
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Institution: | 1. Department of Chemistry, Pohang University of Science and Technology, Pohang, Gyeongbuk, Korea 2. Center for Smart Supramolecules and Division of Advanced Materials Science, Pohang University of Science and Technology, Pohang, Gyeongbuk, Korea
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Abstract: | Noncovalent interactions of cucurbit6]uril (CB6]) with haloacetate and halide anions are investigated in the gas phase using electrospray ionization ion mobility mass spectrometry. Strong noncovalent interactions of monoiodoacetate, monobromoacetate, monochloroacetate, dichloroacetate, and trichloroacetate on the exterior surface of CB6] are observed in the negative mode electrospray ionization mass spectra. The strong binding energy of the complex allows intramolecular SN2 reaction of haloacetate, which yields externally bound CB6]-halide complex, by collisional activation. Utilizing ion mobility technique, structures of exteriorly bound CB6] complexes of haloacetate and halide anions are confirmed. Theoretically determined low energy structures using density functional theory (DFT) further support results from ion mobility studies. The DFT calculation reveals that the binding energy and conformation of haloacetate on the CB6] surface affect the efficiency of the intramolecular SN2 reaction of haloacetate, which correlate well with the experimental observation. |
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