Chromatographically separable rotamers of an unhindered amide

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 rotame...

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Autores principales: Geffe, Mario, Andernach, Lars, Trapp, Oliver, Opatz, Till
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2014
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3999880/
https://www.ncbi.nlm.nih.gov/pubmed/24778722
http://dx.doi.org/10.3762/bjoc.10.63
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author Geffe, Mario
Andernach, Lars
Trapp, Oliver
Opatz, Till
author_facet Geffe, Mario
Andernach, Lars
Trapp, Oliver
Opatz, Till
author_sort Geffe, Mario
collection PubMed
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.
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spelling pubmed-39998802014-04-28 Chromatographically separable rotamers of an unhindered amide Geffe, Mario Andernach, Lars Trapp, Oliver Opatz, Till Beilstein J Org Chem Full Research Paper 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. Beilstein-Institut 2014-03-21 /pmc/articles/PMC3999880/ /pubmed/24778722 http://dx.doi.org/10.3762/bjoc.10.63 Text en Copyright © 2014, Geffe et al. https://creativecommons.org/licenses/by/2.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Geffe, Mario
Andernach, Lars
Trapp, Oliver
Opatz, Till
Chromatographically separable rotamers of an unhindered amide
title Chromatographically separable rotamers of an unhindered amide
title_full Chromatographically separable rotamers of an unhindered amide
title_fullStr Chromatographically separable rotamers of an unhindered amide
title_full_unstemmed Chromatographically separable rotamers of an unhindered amide
title_short Chromatographically separable rotamers of an unhindered amide
title_sort chromatographically separable rotamers of an unhindered amide
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3999880/
https://www.ncbi.nlm.nih.gov/pubmed/24778722
http://dx.doi.org/10.3762/bjoc.10.63
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AT opatztill chromatographicallyseparablerotamersofanunhinderedamide

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