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Lancifodilactone G : insights about an unusually stable enol

Chenoweth, D. M. and Chenoweth, K. and Goddard, W. A., III (2008) Lancifodilactone G : insights about an unusually stable enol. Journal of Organic Chemistry, 73 (17). pp. 6853-6856. ISSN 0022-3263. https://resolver.caltech.edu/CaltechAUTHORS:CHEjoc08

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Abstract

From quantum mechanics calculations we confirm that the naturally occurring enol lancifodilactone G is stable over the keto form (by 2.6 kcal/mol in water), the only known stable aliphatic enol (devoid of conjugated or bulky aromatics and lacking a 1,3-diketone structural motif known to stabilize enols). We determine architectural elements responsible for the enol stabilization and find a mechanism for keto-enol conversion in solution. In addition, we correct previously reported computational results that were performed on the misinterpreted structure demonstrating that the enol form of this natural product is more stable than previously thought.


Item Type:Article
Related URLs:
URLURL TypeDescription
http://dx.doi.org/10.1021/jo8012385DOIUNSPECIFIED
http://pubs.acs.org/doi/abs/10.1021/jo8012385PublisherUNSPECIFIED
Additional Information:© 2008 American Chemical Society. Publication Date (Web): August 7, 2008. D.M.C. is grateful to the Kanel Foundation for a predoctoral fellowship. Partial support was provided by NSF (CMMI-072870 and CTS-0608889). The computational facilities were provided by ARO-DURIP and ONR-DURIP.
Funders:
Funding AgencyGrant Number
Kanel FoundationUNSPECIFIED
NSFCMMI-072870
NSFCTS-0608889
Subject Keywords:CONTINUUM DIELECTRIC THEORY; ACETOPHENONE ENOL; KETONIZATION; EQUILIBRIUM; ENERGIES; GENERATION; MECHANISM; DENSITY.
Issue or Number:17
Record Number:CaltechAUTHORS:CHEjoc08
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:CHEjoc08
Usage Policy:No commercial reproduction, distribution, display or performance rights in this work are provided.
ID Code:13551
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:17 Jun 2009 18:36
Last Modified:03 Oct 2019 00:40

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