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null (Ed.)Quasiracemates – materials consisting of pairs of near enantiomers – form crystalline motifs that mimic the inversion relationships observed for their racemic counterparts. Recent investigations from our group explored a family of chiral ( N -benzoyl)methylbenzylamines to understand the structural boundary of cocrystallization. This investigation extends these earlier studies to include naphthylamide quasiracemates, where the molecular framework is ∼20% larger by volume than the previous diarylamides. A family of naphthylamides was prepared where the pendant functional group differs incrementally in size ( i.e. , H to C 6 H 5 ) to give 55 possible unique pairs of racemic and quasiracemic combinations. Data collected from these materials using X-ray crystallography, thermal analysis methods and lattice energy calculations offer important insight into how a spatially larger naphthylamide molecular framework promotes greater structural variance of substituents during the pairwise assembly of quasienantiomers.more » « less
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Silver, Mark A. ; Cary, Samantha K. ; Garza, Alejandro J. ; Baumbach, Ryan E. ; Arico, Alexandra A. ; Galmin, Gregory A. ; Chen, Kuan-Wen ; Johnson, Jason A. ; Wang, Jamie C. ; Clark, Ronald J. ; et al ( , Journal of the American Chemical Society)