Extreme Oxatriquinanes: Structural Characterization of alpha-Oxyoxonium Species with Extraordinarily Long Carbon-Oxygen Bonds

Date

2013-06-05

Author

Günbaş, Emrullah Görkem
Fettinger, James C.
Olmstead, Marilyn M.
MASCAL, Mark

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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

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Citation Formats

E. G. Günbaş, J. C. Fettinger, M. M. Olmstead, and M. MASCAL, “Extreme Oxatriquinanes: Structural Characterization of alpha-Oxyoxonium Species with Extraordinarily Long Carbon-Oxygen Bonds,” JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, pp. 8173–8176, 2013, Accessed: 00, 2020. [Online]. Available: https://hdl.handle.net/11511/40673.