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...
| Main Authors: | , , , |
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| Format: | Article |
| Language: | English |
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Beilstein-Institut
2014-03-01
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| Series: | Beilstein Journal of Organic Chemistry |
| Subjects: | |
| Online Access: | https://doi.org/10.3762/bjoc.10.63 |
| _version_ | 1829493380207345664 |
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| author | Mario Geffe Lars Andernach Oliver Trapp Till Opatz |
| author_facet | Mario Geffe Lars Andernach Oliver Trapp Till Opatz |
| author_sort | Mario Geffe |
| collection | DOAJ |
| 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. |
| first_indexed | 2024-12-16T06:32:31Z |
| format | Article |
| id | doaj.art-e9d8f857c25b428f8c492be2d1ac0126 |
| institution | Directory Open Access Journal |
| issn | 1860-5397 |
| language | English |
| last_indexed | 2024-12-16T06:32:31Z |
| publishDate | 2014-03-01 |
| publisher | Beilstein-Institut |
| record_format | Article |
| series | Beilstein Journal of Organic Chemistry |
| spelling | doaj.art-e9d8f857c25b428f8c492be2d1ac01262022-12-21T22:40:51ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972014-03-0110170170610.3762/bjoc.10.631860-5397-10-63Chromatographically separable rotamers of an unhindered amideMario Geffe0Lars Andernach1Oliver Trapp2Till Opatz3Institut für Organische Chemie, Johannes Gutenberg Universität Mainz, Duesbergweg 10–14, 55128 Mainz, GermanyInstitut für Organische Chemie, Johannes Gutenberg Universität Mainz, Duesbergweg 10–14, 55128 Mainz, GermanyOrganisch-Chemisches Institut, Ruprecht-Karls Universität Heidelberg, Im Neuenheimer Feld 270, 69120 Heidelberg, GermanyInstitut für Organische Chemie, Johannes Gutenberg Universität Mainz, Duesbergweg 10–14, 55128 Mainz, GermanySurprisingly 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.https://doi.org/10.3762/bjoc.10.63amidesdensity functional calculationsdynamic HPLCrotamersthermodynamics |
| spellingShingle | Mario Geffe Lars Andernach Oliver Trapp Till Opatz Chromatographically separable rotamers of an unhindered amide Beilstein Journal of Organic Chemistry amides density functional calculations dynamic HPLC rotamers thermodynamics |
| 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 | amides density functional calculations dynamic HPLC rotamers thermodynamics |
| url | https://doi.org/10.3762/bjoc.10.63 |
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