Matches in SemOpenAlex for { <https://semopenalex.org/work/W2083144637> ?p ?o ?g. }
- W2083144637 endingPage "10030" @default.
- W2083144637 startingPage "10020" @default.
- W2083144637 abstract "A series of new chiral macrocycles containing the trans-1,2-diaminocyclohexane (DACH) subunit and arene- and oligoethylene glycol-derived spacers has been prepared in enantiomerically pure form. Four of the macrocycles have been characterized by X-ray crystallography, which reveals a consistent mode of intramolecular N–H···N hydrogen bonding and conformational variations about the N-benzylic bonds. Most of the macrocycles were found to differentiate the enantiomers of mandelic acid (MA) by 1H NMR spectroscopy in CDCl3; within the series of macrocycles tested, enantiodiscrimination was promoted by (i) a meta-linkage geometry about the arene spacer, (ii) the presence of naphthalene- rather than phenylene-derived arene spacers, and (iii) increasing length of the oligoethylene glycol bridge. 1H NMR titrations were performed with optically pure MA samples, and the data were fitted to a simultaneous 1:1 and 2:1 binding model, yielding estimates of 2:1 binding constants between some of the macrocycles and MA enantiomers. In several cases, NOESY spectra of the MA:macrocycle complexes show differential intramolecular correlations between protons adjacent to the amine and carboxylic acid groups of the macrocycles and MA enantiomers, respectively, thus demonstrating geometric differences between the diastereomeric intermolecular complexes. The three most effective macrocycles were employed as chiral solvating agents (CSAs) to determine the enantiomeric excess (ee) of 18 MA samples over a wide ee range and with very high accuracy (1% absolute error)." @default.
- W2083144637 created "2016-06-24" @default.
- W2083144637 creator A5000781340 @default.
- W2083144637 creator A5012297054 @default.
- W2083144637 creator A5013410283 @default.
- W2083144637 creator A5058497338 @default.
- W2083144637 creator A5069132052 @default.
- W2083144637 date "2011-11-14" @default.
- W2083144637 modified "2023-10-16" @default.
- W2083144637 title "Aza-Crown Macrocycles as Chiral Solvating Agents for Mandelic Acid Derivatives" @default.
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