Investigation of chiral recognition of 1,1′-bi-2-naphthol enantiomers by heptakis-(2,6-di-O-methyl)-β-cyclodextrin with electrospray mass spectrometry

Chiral recognition of enantiomeric 1,1'-bi-2-naphthol enantiomers by beta- and heptakis-(2,6-di-O-methyl)-beta-cyclodextrins as chiral selectors was investigated by electrospray mass spectrometry. Comparative research shows that both beta-cyclodextrin and heptakis-(2,6-di-O-methyl)-beta-cyclodextrin can form noncovalent complexes with 1,1'-bi-2-naphthol in gas phase. Investigation of tandem mass spectrometric data displays that beta-cyclodextrin has little chiral recognition ability to the enantiomers but heptakis-(2,6-di-O-methyl)-beta-cyclodextrin has strong chiral recognition ability. Our work also displays that mixing ratio of heptakis-(2,6-di-O-methyl)-beta-cyclodextrin to 1,1'-bi-2-naphthol and the collision induced disossiation energy have no effect on chiral recognition.