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- W1513372582 abstract "Abstract The separation of the enantiomers of 4-hydroxy-2-dipropylaminoindan (USDA-46) was accomplished by ion-pair chromatography using benzyloxycarbonylglycyl- l -proline ( l -ZGP) as a chiral selector in the mobile phase. Molecular mechanics calculations (MMX) were performed to model the formation of diastereomeric complexes of l -ZGP and the enantiomers of USDA-46. Complexes were generated by manual dockings of a variety of different conformations of each component and by an automated Monte Carlo search in MacroModel. The complexes were found to be stabilized by a reinforced ionic interaction, inter- and intramolecular hydrogen bonds and attractive aromatic interactions. Geometries and energies of complex conformations were calculated to determine dynamic measures of total and partial surface areas and dipole moments. The results were combined with data from a study on a series of phenolic aminotetralin derivatives. The previously established correlation between the separation coefficient α of the tetralin derivatives and the difference in dynamic unsaturated surface area of the l -ZGP complexes was corroborated by the results obtained with USDA-46." @default.
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- W1513372582 date "1994-04-01" @default.
- W1513372582 modified "2023-09-27" @default.
- W1513372582 title "Chiral discrimination of complexes between benzyloxycarbonylglycyl-l-proline and 4-hydroxy-2-dipropylaminoindan in ion-pair chromatography" @default.
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- W1513372582 doi "https://doi.org/10.1016/0021-9673(94)80414-1" @default.
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