Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
Analysis of the electronic structure of the hydroxymethanes provides a consistent picture of stereoelectronic effects in such molecules: The average C—O bond length decreases in the series methanol, methanediol, methanetriol. An oxygen (O′) lone pair, which is trans-anti-periplanar (app) to another oxygen (O″), shortens and strengthens the C—O′ bond and simultaneously lengthens and weakens the C—O′ bond. This is consistent with solid state structural evidence and with the reactivity patterns of tetrahedral species resulting from nucleophilic addition to a carbonyl group.
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