ORGN 696 |
| Dynamic covalent chemistry, the production of molecular compounds through thermodynamically controlled reactions, has generated much interest of late. Perhaps the most useful facet of this type of chemistry is its ability to error check and proof-read, i.e., that the molecules can equilibrate and adapt to changing reaction conditions in situ. These principles are demonstrated through the construction of the small dynamic combinatorial library made from 2,6-diformylpyridine and 2,2′-oxybis(ethylamine). Electrospray ionization mass spectrometry (ESIMS) confirms the existence of at least nine different linear and cyclic oligomers. Error checking and proof-reading occurs upon the addition of a dialkylammonium ion template – shown in green and blue below – which amplifies a [24]crown-8-like cyclic member of the library during the creation of a [2]rotaxane. Evidence of these processes is presented in the form of one and two-dimensional 1H NMR spectroscopy, variable temperature 1H NMR spectroscopy, and ESIMS.
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Asymmetric Reactions, Combinatorial Chemistry, Molecular Recognition and Self-Assembly, Proteins, Peptides, Amino Acids and Enzyme Inhibitors
8:00 PM-10:00 PM, Wednesday, March 28, 2007 Hyatt Regency Chicago -- Riverside Center, Poster
Division of Organic Chemistry |
