Exploration of the α-effect by substitution on hydroxylamine anions. I. Effects of alkyl- and fluoroalkylation

Many explanations for the alpha-effect have been suggested. Most are simple models conjecturing various sources affecting the nucleophilic behavior. This paper provides a comprehensive study of electronic effects using the single alpha-atom lone electron pair of substituted hydroxyl amine anions. This substituent scheme shows that the interaction of this lone pair with the negatively charged oxygen atom is an important indicator of reactivity.