Extreme oxatriquinanes: Structural characterization of α-oxyoxonium species with extraordinarily long carbon-oxygen bonds

Gorkem Gunbas, William L. Sheppard, James C. Fettinger, Marilyn M. Olmstead, Mark Mascal

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

The first stable α-oxyoxonium species have been synthesized and characterized. Strong donation of nonbonding electrons on oxygen into the adjacent σ(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 α-hydroxy and α-methoxy oxatriquinane triflates reveals 1.658 and 1.619 Å C-O+ bond lengths, respectively, the former of which is a new record for the C-O bond.

Original languageEnglish (US)
Pages (from-to)8173-8176
Number of pages4
JournalJournal of the American Chemical Society
Volume135
Issue number22
DOIs
StatePublished - Jun 5 2013

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Bond length
Carbon
Oxygen
Electrons
Kinetics

ASJC Scopus subject areas

  • Chemistry(all)
  • Catalysis
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Extreme oxatriquinanes : Structural characterization of α-oxyoxonium species with extraordinarily long carbon-oxygen bonds. / Gunbas, Gorkem; Sheppard, William L.; Fettinger, James C.; Olmstead, Marilyn M.; Mascal, Mark.

In: Journal of the American Chemical Society, Vol. 135, No. 22, 05.06.2013, p. 8173-8176.

Research output: Contribution to journalArticle

Gunbas, Gorkem ; Sheppard, William L. ; Fettinger, James C. ; Olmstead, Marilyn M. ; Mascal, Mark. / Extreme oxatriquinanes : Structural characterization of α-oxyoxonium species with extraordinarily long carbon-oxygen bonds. In: Journal of the American Chemical Society. 2013 ; Vol. 135, No. 22. pp. 8173-8176.
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