Investigating the spontaneous resolution of an abiotic metallofoldamer

WCC 14

Ann E. Benavidez, abenavid@udel.edu, Department of Chemistry, University of Delaware, 621 Cedar Avenue, Haddonfield, NJ 08033
Abiotic metallofoldamers are nonbiological molecules based off of salen and salophen ligands which form single-stranded helices upon complexation with metal ions. Although the particular metallofoldamer under investigation is racemic in solution, it spontaneously resolves into enantiomerically pure crystals. I sought to investigate whether a preference exists for either enantiomer and to determine the effectiveness of solid-state circular dichroism spectroscopy as an alternative to x-ray diffraction in spontaneous resolution analysis.

Four crystals were characterized by a previous graduate student and I have examined three additional crystals by solid-state CD, which has been established to efficiently yield reliable results. All seven crystals were found to be left-handed. Currently, I am synthesizing more metallofoldamer so as to gain a larger sample size. It is anticipated that greater insight will be gained concerning the enantiomeric preference of the metallofoldamer and its possible relationship to the issue of the origins of chirality.

 

The Merck Index Women in Chemistry
2:30 PM-4:30 PM, Monday, August 17, 2009 Walter E. Washington Convention Center -- Hall D, Poster

Women Chemists Committee

The 238th ACS National Meeting, Washington, DC, August 16-20, 2009