title: Carbanion or amide? First charge density study of parent 2-picolyllithium.
abstract: The negative charge originating from deprotonation of the methyl group is distributed over the 2-picolyl ring. Bonding properties derived from the electron density distribution support the enamide character of picolyllithium (PicLi; the picture shows the deformation density of [2-PicLi x PicH](2)), but electrophilic attack occurs at the deprotonated C atom. This reactivity is rationalized by the electrostatic potential, which guides electrophiles towards the nucleophilic C atom.
authors.affiliation: Institut für Anorganische Chemie der Universität Göttingen, Tammannstrasse 4, 37077 Göttingen, Germany.
authors.forename: Holger
authors.initials: H
authors.lastname: Ott
authors.forename: Ursula
authors.initials: U
authors.lastname: Pieper
authors.forename: Dirk
authors.initials: D
authors.lastname: Leusser
authors.forename: Ulrike
authors.initials: U
authors.lastname: Flierler
authors.forename: Julian
authors.initials: J
authors.lastname: Henn
authors.forename: Dietmar
authors.initials: D
authors.lastname: Stalke