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Solvent Effects on Nitrogen Chemical Shifts

Review article
Authors Hanna Andersson
Anna-Carin Carlsson
Bijan Nekoueishahraki
Ulrika Brath
Mate Erdelyi
Published in Annual Reports on NMR Spectroscopy
Volume 86
Pages 73-210
ISSN 0066-4103
Publication year 2015
Published at Department of Chemistry and Molecular Biology
Pages 73-210
Language en
Links http://dx.doi.org/10.1016/bs.arnmr...
Keywords 15N NMR; chemical shift, solvent, 14N NMR, peptide, heterocycle,m protein, metal complex
Subject categories Spectroscopy, Physical organic chemistry, Medicinal Chemistry

Abstract

Due to significant developments in cryogenic probe technology and the easy access to inverse detection pulse programmes (HSQC, HMBC), the sensitivity of nitrogen NMR has lately vastly improved. As a consequence, nitrogen NMR has turned into a useful and commonly available tool for solution studies of molecular structure and properties for small organic compounds likewise biopolymers. The high sensitivity of the nitrogen lone pair to changes in the molecular environment, alterations in intra- and intermolecular interactions, and in molecular conformation along with its wide, up to 1200 ppm chemical shift dispersion make nitrogen NMR to an exceptionally sensitive reporter tool. The nitrogen chemical shift has been applied in various fields of chemistry, including for instance the studies of transition metal complexes, chemical reactions such as N-alkylation and N-oxidation, tautomerization, protonation–deprotonation equilibria, hydrogen and halogen bonding, and elucidation of molecular conformation and configuration. The 15N NMR data observed in the investigation of these molecular properties and processes is influenced by the medium it is acquired in. This influence may be due to direct coordination of solvent molecules to transition metal complexes, alteration of tautomerization equilibria, and solvent polarity induced electron density changes of conjugated systems, for example. Thus, the solvent may significantly alter the observed nitrogen NMR shifts. This review aims to provide an overview of solvent effects of practical importance, and discusses selected experimental reports from various subfields of chemistry.

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