Chromatographically separable rotamers of an unhindered amide
- Resource Type
- article
- Authors
- Mario Geffe; Lars Andernach; Oliver Trapp; Till Opatz
- Source
- Beilstein Journal of Organic Chemistry, Vol 10, Iss 1, Pp 701-706 (2014)
- Subject
- amides
density functional calculations
dynamic HPLC
rotamers
thermodynamics
Science
Organic chemistry
QD241-441
- Language
- English
- ISSN
- 1860-5397
Surprisingly stable formamide rotamers were encountered in the tetrahydroisoquinoline and morphinan series of alkaloids. We investigated the hindered rotation around the amide bond by dynamic high-performance liquid chromatography (DHPLC) and kinetic measurements of the interconversion of the rotamers which can readily be separated by HPLC as well as TLC. The experimental results of the different methods were compared to each other as well as to results obtained by DFT calculations.