New deuterium isotope effects on C and F chemical shifts across intramolecular hydrogen bonds of non-resonance assisted systems |
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Authors: | Jacek G So?nicki Poul Erik Hansen |
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Institution: | a Technical University of Szczecin, Institute of Chemistry and Environmental Protection, Al. Piastw 42, PL-71065 Szczecin, Poland b Department of Life Sciences and Chemistry, Roskilde University, PO Box 260, DK-4000 Roskilde, Denmark |
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Abstract: | A series of thioanilides and corresponding anilides, some of which contain fluorinated phenyl rings, have been synthesized as model compounds. They all contain rather strong intramolecular hydrogen bonds, the strength of which varies. Deuterium isotope effects on 19F and 13C chemical shifts due to deuteriation at the NH proton show interesting new long-range isotope effects on chemical shifts that may be related to the existence of an intramolecular hydrogen bond and to transmission of the isotope effect due to an electric field effect. Deuterium isotope effects on chemical shifts report on variations in hydrogen bonding, for example, as a function of changes in substituents or temperature. Deuteriation leads to a strengthening of the hydrogen bond. |
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Keywords: | Hydrogen bond Isotope effect 13C NMR 19F NMR Thioanilides Anilides |
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