Stereoelectronic Properties of Tetrahedral Species derived from Carbonyl Groups. Ab initio study of the hydroxymethanes

✍ Scribed by Jean-Marie Lehn; Georges Wipff; Hans-Beat Bürgi

• Publisher: John Wiley and Sons
• Year: 1974
• Tongue: German
• Weight: 263 KB
• Volume: 57
• Category: Article
• ISSN: 0018-019X
• DOI: 10.1002/hlca.19740570225

✦ Synopsis

Abstract

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.