Journalartikel

Jahr der Veröffentlichung: 2010

Seiten: 7240-7241

Zeitschrift: Journal of the American Chemical Society

Bandnummer: 132

Heftnummer: 21

DOI Link: https://doi.org/10.1021/ja100670q

Verlag: American Chemical Society

Abstract: 

We describe the first preparation of the long-sought parent oxathiirane
from sulfine through photochemical rearrangement with light at λ = 313 ±
10 nm in an Ar matrix at 11 K. Oxathiirane was characterized by the
extraordinarily good agreement of experimentally measured and (unscaled)
CCSD(T)/cc-pVTZ computed vibrational frequencies for both the
perhydrogenated and perdeuterated species. The title molecule is ca. 10
kcal mol⁻¹ less stable than sulfine, in marked contrast to the isomer energy difference of dioxirane vs carbonyl oxide (ca. −25 kcal mol⁻¹).
This is due to the strong positive polarization (blue potential) versus
the highly electronegative oxygen atom (red). The stability ordering
and the relative energy differences of carbonyl versus thiocarbonyl
groups underline the likely role oxathiiranes play in sulfur transfer
reactions.

Harvard-Zitierstil: Schreiner, P., Reisenauer, H., Romanski, J. and Mloston, G. (2010) Oxathiirane, Journal of the American Chemical Society, 132(21), pp. 7240-7241. https://doi.org/10.1021/ja100670q

APA-Zitierstil: Schreiner, P., Reisenauer, H., Romanski, J., & Mloston, G. (2010). Oxathiirane. Journal of the American Chemical Society. 132(21), 7240-7241. https://doi.org/10.1021/ja100670q