Putting Isomers in Their Place

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Science  07 Mar 2003:
Vol. 299, Issue 5612, pp. 1487
DOI: 10.1126/science.299.5612.1487c

Normally the isomers of chemical compounds are defined by different sets of covalent bonds or by different stereochemical arrangements at chiral centers. Shivanyuk and Rebek demonstrate a further type of isomerization by trapping guest molecules in molecular capsules. Three molecules of chloroform (CHCl3; 74 cubic angstroms) or isopropyl chloride [ClCH(CH3)2; 73 cubic angstroms] fit snugly in a 420 cubic angstrom cavity formed by two cavitand molecules. Nuclear magnetic resonance studies show that all six possible arrangements of three guest molecules can be identified. These structures are dynamic, so they can start with the complex containing three isopropyl chloride molecules and titrate in chloroform to create the other isomers. — PDS

Angew. Chem. Int. Ed. 42, 684 (2003).

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