CHED 412 |
| Pairs of benzylideneanilines we have designated “bridge-flipped isomers” differ only in the orientation of the chain or bridge of atoms connecting the two aryl groups; the isomerism is Ar-CH=N-Ar' vs. Ar-N=CH-Ar'. Our goal is to prepare new solid materials having properties that can be controlled or modified by co-crystallizing various proportions of bridge-flipped benzylideneaniline isomers. Mutual solid-state solubility is most extensive for components that have the same molecular packing arrangement in their respective crystals, so we are preparing benzylideneaniline bridge-flipped isomeric pairs and determining their crystal structures to identify isostructural pairs that would be especially suitable for co-crystallization. Among these structures we have recently discovered our first isostructural pair: 2-trifluoromethyl-N-(2-methylbenzylidene)aniline and 2-methyl-N-(2-trifluoromethylbenzylidene)aniline. Unlike the only other isostructural bridge-flipped benzylideneanilines of which we are currently aware, 4-chloro-N-(4-methylbenzylidene)aniline and 4-methyl-N-(4-chlorobenzylidene)aniline, our compounds assume an ordered molecular packing arrangement in the solid state. |
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Undergraduate Research Poster Session: Organic Chemistry
11:00 AM-1:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- Ex. Hall B4, Poster
Division of Chemical Education |