Matches in SemOpenAlex for { <https://semopenalex.org/work/W2067841092> ?p ?o ?g. }
- W2067841092 endingPage "17976" @default.
- W2067841092 startingPage "17966" @default.
- W2067841092 abstract "We report that the p-xylylenediammonium ion (11) acts as a template in the cucurbit[n]uril forming reaction that biases the reaction toward the production of methylene bridged glycoluril hexamer (6C) and bis-nor-seco-CB[10]. Hexamer 6C is readily available on the gram scale by a one step synthetic procedure that avoids chromatography. Hexamer 6C undergoes macrocylization with (substituted) phthalaldehydes 12, 14, 15, and 18—in 9 M H2SO4 or concd HCl at room temperature to deliver monofunctionalized CB[6] derivatives 13, 16, 17, and 19—that are poised for further functionalization reactions. The kinetics of the macrocyclization reaction between hexamer and formaldehyde or phthalaldehyde depends on the presence and identity of ammonium ions as templates. p-Xylylenediammonium ion (11) which barely fits inside CB[6] sized cavities acts as a negative template which slows down transformation of 6C and paraformaldehyde into CB[6]. In contrast, 11 and hexanediammonium ion (20) act as a positive template that promotes the macrocyclization reaction between 6C and 12 to deliver (±)-21 as a key intermediate along the mechanistic pathway to CB[6] derivatives. Naphthalene-CB[6] derivative 19 which contains both fluorophore and ureidyl C═O metal-ion (e.g., Eu3+) binding sites forms the basis for a fluorescence turn-on assay for suitable ammonium ions (e.g., hexanediammonium ion and histamine)." @default.
- W2067841092 created "2016-06-24" @default.
- W2067841092 creator A5004743509 @default.
- W2067841092 creator A5022148690 @default.
- W2067841092 creator A5028917390 @default.
- W2067841092 creator A5068678304 @default.
- W2067841092 creator A5068983305 @default.
- W2067841092 creator A5082197325 @default.
- W2067841092 creator A5087568390 @default.
- W2067841092 date "2011-10-17" @default.
- W2067841092 modified "2023-10-18" @default.
- W2067841092 title "Templated Synthesis of Glycoluril Hexamer and Monofunctionalized Cucurbit[6]uril Derivatives" @default.
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