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The solid state structures of three compounds that contain a perfluorinated chain, CF (3) (CF (2) ) (5) CH (2) CH (CH (3) ) CO (2) H, CF (3) (CF (2) ) (5) (CH (2) ) (4) (CF (2) ) (5) CF (3) and CF (3) (CF (2) ) (5) CH (2) CH (2) (3) P═O have been compared and a number of C-F···F-C and C-F···H-C interactions that are closer than the sum of the van der Waals radii have been identified. These interactions have been probed by a comprehensive computational chemistry investigation and the stabilizing energy between dimeric fragments was found to be 0. 26-29. 64 kcal/mol, depending on the type of interaction. An Atoms-in-Molecules (AIM) study has confirmed that specific C-F···F-C interactions are indeed present, and are not due simply to crystal packing. The weakly stabilizing nature of these interactions has been utilized in the physisorption of a selected number of compounds containing long chain perfluorinated ponytails onto a perfluorinated self-assembled monolayer, which has been characterized by IRRAS (Infrared Reflection Absorption Spectroscopy).
Baker et al. (Sun,) studied this question.