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Homoanomeric effect in the 1,2-dimethoxyethyl radical

Henry, D.J.ORCID: 0000-0002-9629-4423, Beckwith, A.L.J. and Radom, L. (2003) Homoanomeric effect in the 1,2-dimethoxyethyl radical. Australian Journal of Chemistry, 56 (5). pp. 429-436.

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A homoanomeric effect is found to stabilize the 1,2-dimethoxyethyl radical (CH3O-C•H-CH2OCH3) in a conformation in which the singly-occupied orbital at the radical centre is approximately coplanar with the p-type lone pair on the α-oxygen and with the β-C-O bond. The magnitude of this stabilization is predicted to be ∼ 10-12 kJ mol-1 at the G3(MP2)-RAD and DBS-RAD levels of theory.

Item Type: Journal Article
Publisher: Commonwealth Scientific and Industrial Research Organization Publishing
Copyright: © CSIRO 2003
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