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

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Article information

DOI
https://doi.org/10.1039/C8CC09987A
Article type
Communication
Submitted
17 Dec 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

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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

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