2014
DOI: 10.1038/nchem.1842
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Induced-fit catalysis of corannulene bowl-to-bowl inversion

Abstract: Stereoelectronic complementarity between the active site of an enzyme and the transition state of a reaction is one of the tenets of enzyme catalysis. This report illustrates the principles of enzyme catalysis (first proposed by Pauling and Jencks) through a well-defined model system that has been fully characterized crystallographically, computationally and kinetically. Catalysis of the bowl-to-bowl inversion processes that pertain to corannulene is achieved by combining ground-state destabilization and trans… Show more

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Cited by 154 publications
(109 citation statements)
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“…Siegel and co-workers studied the bowl-to-bowl inversion of corannulene 1 and ethylcorannulene derivatives mediated by extended tetracationic cyclophane (Figure 8) [22,30]. This synthetic host forms a supramolecular complex with 1 and ethylcorannulene via induced fit, and the bowl-to-bowl inversion process was accelerated by a factor of 10 at room temperature.…”
Section: Bowl Inversion/racemization Of Chiral Buckybowlsmentioning
confidence: 99%
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“…Siegel and co-workers studied the bowl-to-bowl inversion of corannulene 1 and ethylcorannulene derivatives mediated by extended tetracationic cyclophane (Figure 8) [22,30]. This synthetic host forms a supramolecular complex with 1 and ethylcorannulene via induced fit, and the bowl-to-bowl inversion process was accelerated by a factor of 10 at room temperature.…”
Section: Bowl Inversion/racemization Of Chiral Buckybowlsmentioning
confidence: 99%
“…and co-workers found that sumanene 2 attached with a mono-iodo substituent induces a slightly deeper bowl depth and a higher bowl inversion energy compared with other sumanene derivatives because of its steric effect, whereas the electronic effects caused by formyl and nitro substituents induced a shallower bowl depth and a lower bowl inversion energy [20]. Siegel and co-workers studied the bowl-to-bowl inversion of corannulene 1 and ethylcorannulene derivatives mediated by extended tetracationic cyclophane (Figure 8) [22,30]. This synthetic host forms a supramolecular complex with 1 and ethylcorannulene via induced fit, and the bowl-to-bowl inversion process was accelerated by a factor of 10 at room temperature.…”
Section: Bowl Inversion/racemization Of Chiral Buckybowlsmentioning
confidence: 99%
See 3 more Smart Citations