title: Controlling factors in the synthesis of cucurbituril and its homologues.
abstract: The acid-catalyzed synthesis of cucurbit[n]urils from formaldehyde and glycoluril is poorly understood. In this paper, we examine a wide range of reaction conditions that include the effects of acid type, acid concentration, reactant concentrations, and temperature to both probe the mechanism and optimize the yields of isolated cucurbit[n]urils, where n = 5-10. A mechanism for the formation of these cucurbit[n]urils is presented. Individual cucurbit[n]urils were unambiguously identified in reaction mixtures using ESMS and (13)C NMR.
authors.affiliation: School of Chemistry, University College, University of New South Wales, Australian Defence Force Academy, Canberra, ACT 2600, Australia.
authors.forename: A
authors.initials: A
authors.lastname: Day
authors.forename: A P
authors.initials: AP
authors.lastname: Arnold
authors.forename: R J
authors.initials: RJ
authors.lastname: Blanch
authors.forename: B
authors.initials: B
authors.lastname: Snushall