Homoanomeric effect in the 1,2-dimethoxyethyl radical

David J. Henry; Athelstan L.J. Beckwith; Leo Radom

doi:10.1071/CH02255

Homoanomeric effect in the 1,2-dimethoxyethyl radical

David J. Henry^*, Athelstan L.J. Beckwith, Leo Radom

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

5 Citations (Scopus)

Abstract

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.

Original language	English
Pages (from-to)	429-436
Number of pages	8
Journal	Australian Journal of Chemistry
Volume	56
Issue number	5
DOIs	https://doi.org/10.1071/CH02255
Publication status	Published - 2003

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title = "Homoanomeric effect in the 1,2-dimethoxyethyl radical",

abstract = "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.",

author = "Henry, {David J.} and Beckwith, {Athelstan L.J.} and Leo Radom",

year = "2003",

doi = "10.1071/CH02255",

language = "English",

volume = "56",

pages = "429--436",

journal = "Australian Journal of Chemistry",

issn = "0004-9425",

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T1 - Homoanomeric effect in the 1,2-dimethoxyethyl radical

AU - Henry, David J.

AU - Beckwith, Athelstan L.J.

AU - Radom, Leo

PY - 2003

Y1 - 2003

N2 - 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.

AB - 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.

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U2 - 10.1071/CH02255

DO - 10.1071/CH02255

M3 - Article

SN - 0004-9425

VL - 56

SP - 429

EP - 436

JO - Australian Journal of Chemistry

JF - Australian Journal of Chemistry

IS - 5

ER -

Homoanomeric effect in the 1,2-dimethoxyethyl radical

Abstract

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