C-hexaphenyl-substituted trianglamine as a chiral solvating agent for carboxylic acids

Chiral hexaazamacrocycles with a trianglamine structure and C(3)-symmetry, containing six ring substituents and twelve stereocenters have been tested as chiral solvating agents (CSAs) for α-substituted carboxylic acids. Excellent results have been obtained with a hexaphenyl-substituted macrocycle. T...

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Bibliographic Details
Published inOrganic & biomolecular chemistry Vol. 9; no. 11; p. 4234
Main Authors Gualandi, Andrea, Grilli, Stefano, Savoia, Diego, Kwit, Marcin, Gawroński, Jacek
Format Journal Article
LanguageEnglish
Published England 07.06.2011
Subjects
Amines - chemistry
Carboxylic Acids - chemistry
Magnetic Resonance Spectroscopy
Molecular Conformation
Quantum Theory
Stereoisomerism
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ISSN1477-0520
1477-0539
1477-0539
DOI10.1039/c0ob01192d

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Summary:Chiral hexaazamacrocycles with a trianglamine structure and C(3)-symmetry, containing six ring substituents and twelve stereocenters have been tested as chiral solvating agents (CSAs) for α-substituted carboxylic acids. Excellent results have been obtained with a hexaphenyl-substituted macrocycle. The optimal ratio between the macrocycle and racemic acid, allowing for baseline separation of the enantiomers' signals in the (1)H NMR spectrum, was dependent on the type of acid, in particular on its degree of acidity. The analyte and the CSA could be separated and recovered by a simple acid-base extraction and reused without purification. The conformations of the free and protonated hexaamino macrocycles were inferred by CD spectroscopic studies and DFT calculations.
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ISSN:1477-0520
1477-0539
1477-0539
DOI:10.1039/c0ob01192d