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Extreme Oxatriquinanes: Structural Characterization of alpha-Oxyoxonium Species with Extraordinarily Long Carbon-Oxygen Bonds
Date
2013-06-05
Author
Günbaş, Emrullah Görkem
Sheppard, William L.
Fettinger, James C.
Olmstead, Marilyn M.
MASCAL, Mark
Metadata
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This work is licensed under a
Creative Commons Attribution-NonCommercial-NoDerivatives 4.0 International License
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The first stable alpha-oxyoxonium species have been synthesized and characterized. Strong donation of nonbonding electrons on oxygen into the adjacent sigma*(C-O+) orbital was predicted by modeling to result in unheard of carbon-oxygen bond lengths. The kinetic stability of the triquinane ring system provides a platform upon which to study these otherwise elusive species, which are evocative of intermediates on the acetalization reaction pathway. Crystallographic analysis of the alpha-hydroxy and alpha-methoxy oxatriquinane triflates reveals 1.658 and 1.619 angstrom C-O+ bond lengths, respectively, the former of which is a new record for the C-O bond.
Subject Keywords
Colloid and Surface Chemistry
,
Biochemistry
,
General Chemistry
,
Catalysis
URI
https://hdl.handle.net/11511/40673
Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
DOI
https://doi.org/10.1021/ja4032715
Collections
Department of Chemistry, Article