New Chiral Cyclohexylhemicucurbit[6]uril
- 11 July 2013
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 15 (14), 3786-3789
- https://doi.org/10.1021/ol401766a
Abstract
The first enantiomerically pure members of the cucurbituril family, (all-S)- and (all-R)-cyclohexylhemicucurbit[6]urils (cycHC), were synthesized in good yield (up to 85%). The crystal structure of this new macrocycle clearly shows its ball-like shape. CycHC monomers adopt a “zigzag” conformation, having apolar cyclohexyls around the openings and polar ureas in the middle. Cyclohexylhemicucurbit[6]urils formed complexes with halides, carboxylic acids and amines and diastereomeric complexes with methoxyphenylacetic acid in organic media. The association constants of cycHC with small organic compounds were evaluated by diffusion NMR in chloroform.Keywords
This publication has 35 references indexed in Scilit:
- Acyclic Cucurbit[n]uril‐Type Molecular Containers Bind Neuromuscular Blocking Agents In Vitro and Reverse Neuromuscular Block In VivoAngewandte Chemie, 2012
- Recognition Properties of Acyclic Glycoluril OligomersOrganic Letters, 2011
- Bambus[n]urils: a New Family of Macrocyclic Anion ReceptorsOrganic Letters, 2011
- Anion‐Free Bambus[6]uril and Its Supramolecular PropertiesChemistry – A European Journal, 2011
- Acyclic Cucurbit[n]uril Congeners Are High Affinity HostsThe Journal of Organic Chemistry, 2010
- Cucurbit[n]urils: from mechanism to structure and functionChemical Communications, 2008
- The Inverted Cucurbit[n]uril FamilyJournal of the American Chemical Society, 2005
- Acyclic Congener of Cucurbituril: Synthesis and Recognition PropertiesThe Journal of Organic Chemistry, 2003
- A Method for Synthesizing Partially Substituted Cucurbit[n]urilMolecules, 2003
- Diffusion ordered nuclear magnetic resonance spectroscopy: principles and applicationsProgress in Nuclear Magnetic Resonance Spectroscopy, 1999