Issue 16, 2019
From the journal:

Chemical Communications

Combined experimental and theoretical study of long-range H–F interactions in α-fluoro amides†

Elena Cosimi, ORCID logo a   Nils Trapp, ORCID logo a   Marc-Olivier Ebert ORCID logo *a  and  Helma Wennemers ORCID logo *a  

* Corresponding authors

a Laboratory of Organic Chemistry, D-CHAB, ETH Zurich, Vladimir-Prelog-Weg 3, CH-8093 Zurich, Switzerland
E-mail: Marc-Olivier.Ebert@org.chem.ethz.ch, Helma.Wennemers@org.chem.ethz.ch

Abstract

A combined experimental and computational approach provided insight into the nature and conformational dependence of long-range 4JHF couplings in α-fluoro amides. The dependence of 4JHF on substituents and the solvent was investigated. H–F coupling constants determined by NMR spectroscopy are in agreement with DFT calculations. NBO analysis revealed that a favourable nF→σNH* interaction correlates with the magnitude of 4JHF.

Graphical abstract: Combined experimental and theoretical study of long-range H–F interactions in α-fluoro amides

About
Cited by
Related
Download options Please wait...

Supplementary files

Article information

DOI
https://doi.org/10.1039/C8CC09987A
Article type
Communication
Submitted
17 Dis 2018
Accepted
16 Jan 2019
First published
16 Jan 2019
This article is Open Access
Creative Commons BY-NC license

Chem. Commun., 2019,55, 2253-2256

Permissions

Request permissions

Combined experimental and theoretical study of long-range H–F interactions in α-fluoro amides

E. Cosimi, N. Trapp, M. Ebert and H. Wennemers, Chem. Commun., 2019, 55, 2253 DOI: 10.1039/C8CC09987A

This article is licensed under a Creative Commons Attribution-NonCommercial 3.0 Unported Licence. You can use material from this article in other publications, without requesting further permission from the RSC, provided that the correct acknowledgement is given and it is not used for commercial purposes.

To request permission to reproduce material from this article in a commercial publication, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party commercial publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements