English   español  
Please use this identifier to cite or link to this item: http://hdl.handle.net/10261/213295
logo share SHARE logo core CORE   Add this article to your Mendeley library MendeleyBASE

Visualizar otros formatos: MARC | Dublin Core | RDF | ORE | MODS | METS | DIDL
Exportar a otros formatos:


On the Configuration of Five‐Membered Rings: A Spin–Spin Coupling Constant Approach

AuthorsNapolitano, José G.; Gavín, José A.; García, Celina; Norte, Manuel; Fernández, José J.; Hernández Daranas, Antonio
KeywordsAb initio calculations
Coupling constants
Five‐membered rings
NMR spectroscopy
Issue Date27-May-2011
CitationChemistry - a European Journal 17(23): 6338-6347 (2011)
AbstractFive‐membered rings are clearly among the most common structural motifs found in chemistry and biology. Nevertheless, the configuration of conformationally mobile five‐membered rings is often difficult to assign from nuclear magnetic resonance (NMR) data. A simple, reliable, and efficient approach for the stereochemical analysis of five‐membered rings based on the measurement of NMR coupling constants is presented. Density functional theory calculations using representative conformations of the full conformational space available to rings with different substitution patterns were used to identify differences between the accessible coupling constant values for cis and trans relative orientations of the substituents. The calculations were assessed experimentally using NMR data obtained from a number of models. This approach can be easily used to analyze different five‐membered rings, such as oxolanes, cyclopentanes, furanosides and pyrrolidines, and their relative configuration can be determined without the need for making further conformational considerations.
Publisher version (URL)https://doi.org/10.1002/chem.201100412
Appears in Collections:(IPNA) Artículos
Files in This Item:
File Description SizeFormat 
accesoRestringido.pdfArtículo principal16,34 kBAdobe PDFThumbnail
Show full item record
Review this work

Related articles:

WARNING: Items in Digital.CSIC are protected by copyright, with all rights reserved, unless otherwise indicated.