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Host-Guest Complexes of Cucurbit[6]uril with Phenethylamine-Type Stimulants

Abstract

The host-guest complexes between cucurbit[6]uril macrocycle and phenethylamine ‘natural’ stimulants (ephedrine, synephrine and octopamine) have been obtained in the presence of magnesium ions. Ephedrine and synephrine form partially inclusion complexes with the macrocycle upon insertion of the methylammonium moieties into host cavity and stabilizing ion-dipole and hydrogen bonding interactions. Octopamine lacking methyl group attached to the ammonium function forms perching complexes with the macrocycle. While magnesium ions used to enchence aqueous solubility of cucurbit[6]uril do not interfere in the crystallization of ephedrine and synephrine host-guest complexes, in the case of octopamine the sequential crystallization of metastable metal-free host-guest complex and thermodynamically stable magnesium-captured form of the host-guest complexes was observed.

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Publication details

The article was received on 28 Sep 2018, accepted on 06 Nov 2018 and first published on 06 Nov 2018


Article type: Communication
DOI: 10.1039/C8CE01661E
Citation: CrystEngComm, 2018, Accepted Manuscript
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    Host-Guest Complexes of Cucurbit[6]uril with Phenethylamine-Type Stimulants

    O. Danylyuk, CrystEngComm, 2018, Accepted Manuscript , DOI: 10.1039/C8CE01661E

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