Carbanion or amide? First charge density study of parent 2-picolyllithium.
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.
Ott
Holger
H
Institut für Anorganische Chemie der Universität Göttingen, Tammannstrasse 4, 37077 Göttingen, Germany.
Pieper
Ursula
U
Leusser
Dirk
D
Flierler
Ulrike
U
Henn
Julian
J
Stalke
Dietmar
D