Chromatographically separable rotamers of an unhindered amide

6533b82cfe1ef96bd128ebde

RESEARCH PRODUCT

Chromatographically separable rotamers of an unhindered amide

Till Opatz Lars Andernach Oliver Trapp Mario Geffe

subject

Formamide Morphinan Tetrahydroisoquinoline dynamic HPLC Organic Chemistry rotamers High-performance liquid chromatography Full Research Paper amides lcsh:QD241-441 Chemistry thermodynamics chemistry.chemical_compound lcsh:Organic chemistry chemistry Computational chemistry Amide density functional calculations Organic chemistry Peptide bond lcsh:Q lcsh:Science Conformational isomerism

description

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.

year	journal	country	edition	language
2014-01-10	Beilstein Journal of Organic Chemistry

https://doi.org/10.3762/bjoc.10.63

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