An INDO molecular orbital study of [1,3]π interactions in 2-substituted allyl cations

Abstract

The INDO molecular orbital technique, including a partial geometry search, has been applied to three 2-substituted allyl cations and the parent allyl cation. It is deduced that electron-releasing substituents favour π bonding between the terminal carbons. The 2-oxidoallyl species is found to represent an extreme example of this effect, the [1,3]π interaction being so pronounced that 2-oxidoallyl appears to be best described as a monohomocyclopropenone.