Tuning the steric hindrance of alkylamines: a predictive model of steric editing of planar amines.

ABSTRACT: Amines are one of the most prevalent functional groups in chemistry. Perhaps even more importantly, amines represent one of the most ubiquitous moieties within the realm of bioactive natural products and life-saving pharmaceuticals. The archetypal geometrical property of amines is their sp³ hybridization with the lone pair of nitrogen occupying the apex of the pyramid. Herein, we present a blueprint for quantifying the properties of extremely sterically hindered alkylamines. These amines reach planarity around the nitrogen atom due to the excessive steric hindrance, which results in a conformational re-modeling of the amine moiety. Crucially, the steric properties of amines are characterized by the %V _Bur index, which we show is a general predictive parameter f

SUBMITTER: Tomasini M 

PROVIDER: S-EPMC11339794 | biostudies-literature | 2024 Aug

REPOSITORIES: biostudies-literature