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Amino alcohol based chiral solvating agents: synthesis and applications in the NMR enantiodiscrimination of carboxylic acids

Bozkurt, Selahattin; Durmaz, Mustafa; Naziroglu, Hayriye Nevin; Yilmaz, Mustafa; Sirit, Abdulkadir


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  <dc:creator>Bozkurt, Selahattin</dc:creator>
  <dc:creator>Durmaz, Mustafa</dc:creator>
  <dc:creator>Naziroglu, Hayriye Nevin</dc:creator>
  <dc:creator>Yilmaz, Mustafa</dc:creator>
  <dc:creator>Sirit, Abdulkadir</dc:creator>
  <dc:date>2011-01-01</dc:date>
  <dc:description>Four optically active amino alcohols were synthesized via the ring opening of (R)-N-(2,3-epoxypropyl)phthalimide with (R)-2-phenyl glycinol, (1R,2S)-cis-1-amino-2-indanol, (R)-2-amino-1-butanol and (S)-phenyl ethylamine in 73-93% yields. The enantioselective recognition of these receptors towards the enantiomers of racemic carboxylic acids was studied by H-1 NMR spectroscopy. The molar ratio and the association constants of the chiral compounds with each of the enantiomers of the guests were determined by using Job plots and a non-linear least-squares fitting method, respectively. Large non-equivalent chemical shifts (up to 30.0 Hz) can be achieved in the presence of chiral amino alcohols 2 and 5. Amongst the chiral receptors used, compound 5 was found to be the best chiral shift reagent, and was effective in the determination of the enantiomeric excess of chiral carboxylic acids. (C) 2011 Elsevier Ltd. All rights reserved.</dc:description>
  <dc:identifier>https://aperta.ulakbim.gov.trrecord/21751</dc:identifier>
  <dc:identifier>oai:zenodo.org:21751</dc:identifier>
  <dc:rights>info:eu-repo/semantics/openAccess</dc:rights>
  <dc:rights>http://www.opendefinition.org/licenses/cc-by</dc:rights>
  <dc:source>TETRAHEDRON-ASYMMETRY 22(5) 541-549</dc:source>
  <dc:title>Amino alcohol based chiral solvating agents: synthesis and applications in the NMR enantiodiscrimination of carboxylic acids</dc:title>
  <dc:type>info:eu-repo/semantics/article</dc:type>
  <dc:type>publication-article</dc:type>
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