Conformational Study of N,N'-Diacyl Bispidines and Dioxo Bis-bispidines: Planar Chirality and Molecular Switching
Zhuo Wang1, Md Jahirul Islam1, V Nicholas Vukotic1
1Department of Chemistry and Biochemistry, University of Windsor , 401 Sunset Avenue, Windsor, Ontario N9B 3P4, Canada.
Abstract:
N,N'-Diacyl bispidines exhibit chirality in the absence of a chiral center and axis. Conformational analysis indicates planar chirality in the molecular structure as a result of open-ended chiral planes, which has been confirmed by X-ray diffraction studies. Substantial chiral-achiral molecular switching is observed in di(haloacetyl) bispidines upon changing the solvent polarity. Tethering the chiral planes with a bispidine linker alters the planar chirality significantly and renders the resulting bis-bispidine macrocycles achiral.
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