Chromatographically separable rotamers of an unhindered amide

Publication type:
Journal article
Metadata:
Autoren
  • Mario Geffe
  • Lars Andernach
  • Oliver Trapp
  • Till Opatz
Sammlungen
  • metadata
ISSN
1860-5397
Zeitschrift
Beilstein journal of organic chemistry
Schlüsselwörter
  • 540 Chemie
  • 540 Chemistry and allied sciences
Sprache
eng
Paginierung
Seiten: 701 - 706
Datum der Veröffentlichung
2014
Herausgeber
Beilstein-Institut zur Förderung der Chemischen Wissenschaften
Herausgeber URL
http://dx.doi.org/10.3762/bjoc.10.63
Datum der Datenerfassung
2020
Datum, an dem der Datensatz öffentlich gemacht wurde
2020
Zugang
Public
Titel
Chromatographically separable rotamers of an unhindered amide
Ausgabe der Zeitschrift
10

Data source: METADATA.UB

Other metadata sources:
Autoren
  • Mario Geffe
  • Lars Andernach
  • Oliver Trapp
  • Till Opatz
Autoren-URL
https://www.webofscience.com/api/gateway?GWVersion=2&SrcApp=fis-test-1&SrcAuth=WosAPI&KeyUT=WOS:000333306800001&DestLinkType=FullRecord&DestApp=WOS_CPL
DOI
10.3762/bjoc.10.63
Externe Identifier
  • Clarivate Analytics Document Solution ID: AD5PZ
  • PubMed Identifier: 24778722
ISSN
1860-5397
Zeitschrift
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
Schlüsselwörter
  • amides
  • density functional calculations
  • dynamic HPLC
  • rotamers
  • thermodynamics
Paginierung
701 - 706
Datum der Veröffentlichung
2014
Status
Published
Titel
Chromatographically separable rotamers of an unhindered amide
Sub types
  • Article
Ausgabe der Zeitschrift
10

Data source: Web of Science (Lite)

Abstract
<jats:p>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.</jats:p>
Date of acceptance
2014
Autoren
  • Mario Geffe
  • Lars Andernach
  • Oliver Trapp
  • Till Opatz
DOI
10.3762/bjoc.10.63
eISSN
1860-5397
Zeitschrift
Beilstein Journal of Organic Chemistry
Sprache
en
Online publication date
2014
Paginierung
701 - 706
Status
Published online
Herausgeber
Beilstein Institut
Herausgeber URL
http://dx.doi.org/10.3762/bjoc.10.63
Datum der Datenerfassung
2021
Titel
Chromatographically separable rotamers of an unhindered amide
Ausgabe der Zeitschrift
10

Data source: Crossref

Abstract
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.
Addresses
  • Institut für Organische Chemie, Johannes Gutenberg Universität Mainz, Duesbergweg 10-14, 55128 Mainz, Germany.
Autoren
  • Mario Geffe
  • Lars Andernach
  • Oliver Trapp
  • Till Opatz
DOI
10.3762/bjoc.10.63
eISSN
1860-5397
Externe Identifier
  • PubMed Identifier: 24778722
  • PubMed Central ID: PMC3999880
Open access
true
ISSN
1860-5397
Zeitschrift
Beilstein journal of organic chemistry
Sprache
eng
Medium
Electronic-eCollection
Online publication date
2014
Open access status
Open Access
Paginierung
701 - 706
Datum der Veröffentlichung
2014
Status
Published
Publisher licence
CC BY
Datum der Datenerfassung
2014
Titel
Chromatographically separable rotamers of an unhindered amide.
Sub types
  • research-article
  • Journal Article
Ausgabe der Zeitschrift
10

Files

https://www.beilstein-journals.org/bjoc/content/pdf/1860-5397-10-63.pdf https://www.ncbi.nlm.nih.gov/pmc/articles/pmid/24778722/pdf/?tool=EBI https://europepmc.org/articles/PMC3999880?pdf=render

Data source: Europe PubMed Central

Abstract
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.
Date of acceptance
2014
Autoren
  • Mario Geffe
  • Lars Andernach
  • Oliver Trapp
  • Till Opatz
Autoren-URL
https://www.ncbi.nlm.nih.gov/pubmed/24778722
DOI
10.3762/bjoc.10.63
Externe Identifier
  • PubMed Central ID: PMC3999880
ISSN
1860-5397
Zeitschrift
Beilstein J Org Chem
Schlüsselwörter
  • amides
  • density functional calculations
  • dynamic HPLC
  • rotamers
  • thermodynamics
Sprache
eng
Country
Germany
Paginierung
701 - 706
Datum der Veröffentlichung
2014
Status
Published online
Datum, an dem der Datensatz öffentlich gemacht wurde
2014
Titel
Chromatographically separable rotamers of an unhindered amide.
Sub types
  • Journal Article
Ausgabe der Zeitschrift
10

Data source: PubMed

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