Perfluorochemicals (PFCs) are well known for their accumulation and persistence in the environment, primarily due to their inability to degrade in part due to high bond enthalpy of C-F bonds. Aside from these chemicals being hydrophobic and oleophobic, they display a helical conformation, which we hypothesize contributes to their non-reactiveness. We investigated the dependence of perfluoroalkyl chains on helicity, specifically that helicity becomes a more prominent influence on the structure as the number of carbons per chain increases. Density Functional Theory computations were used to perform charge and natural bond orbital analysis to look for the possibility of agnostic-type interactions. Potential energy surfaces of perfluoroalkyl chain were scanned in order to understand their stability and conformations. The results of the scans showed that compared to their hydrogen analogues, as the perfluoroalkyl chains increased, more energy minima were observed. Moreover, these molecules would likely become radicals during an oxidative treatment process, we also investigated how the helicity plays a role in the nature of these radicals. These findings of how the helicity contributes to the energy, charge, and spin of perfluoroalkyl molecules will be presented.

Helical nature of perflurochemicals and its implications

252nd National Meeting (2016)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.