Recently, our research group demonstrated the importance of molecular shape to the recognition profiles of a family of diarylamide quasiracemates. This system consisted of chiral 2-substitituted (N-benzoyl)methylbenzylamines and provided a catalog of molecules that differed incrementally in the spatial properties of the altered substituent. Pairs of these compounds, i.e., quasiracemates composed of <i>R</i>-X and <i>S</i>-X’, were processed via hot stage thermomicroscopy to give outcomes that helped assign the structural boundaries of molecular shape to molecular assembly. This investigation extends these studies to include naphthylamide quasiracemates, which has a molecular framework that is ~20% larger than the previous diarylamides. Expanding on previous research, the question was asked of whether increasing the size of the chemical framework would allow for greater topological diversity of substituents in quasiracemate formation. This has been pursued by synthesizing an extensive set of chiral naphthylamide quasienantiomers capable of forming bimolecular assemblies in molecular crystals. These samples have been assessed using X-ray crystallography, DSC, and hot stage microscopy with results that offer important insight to the structural features responsible for quasiracemate formation.

Effects of increasing size of molecular framework on crystal recognition in naphthylamide quasiracemates

256th National Meeting (2018)

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