Behavior of the 9-anthryl-tert-butylcarbinol as a chiral solvating agent.: Study of diastereochemical association by intermolecular NOE and molecular dynamics calculations

The 9-anthryl-tert-butylcarbinol was tested as a chiral solvating agent (CSA) in the presence of racemic forms of mentil-p-toluenesulfinate, 9-( 1-amino-2,2-dimethylpropyl)-9,19-dihydroanthracene, alpha-methoxyphenylacetic acid and 1-phenyl-1,2-ethanediol. Diastereomeric complexes were found to form between each enantiomer of these last two compounds. One of the enantiomers of 9-anthryl-tert-butylcarbinol was studied by means of intermolecular NOE and molecular dynamics calculations. Major thermodynamic and structural differences were found.