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Secondary Isotope Effects on 13C and 15N Chemical Shifts of Schiff Bases Revisited
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Alexander Filarowski
Published/Copyright:
June 10, 2013
Abstract
An analysis is presented of secondary deuterium isotope effects on 15N and 13C chemical shifts of the methylamine Schiff base of 4,6-dimethoxysalicylaldehyde. It is shown that for this compound existing as an equilibrium between an OH and a NH-form, the secondary isotope effects depend on the OH/NH ratio giving a function with a maximum and a minimum.
Secondary deuterium isotope effects on 13C and 15N chemical shifts are compared in a broader range of compounds and the above trend is confirmed. Changes in the dielectric constants of the medium with temperature are found to be rather unimportant for the change in equilibrium. Equilibrium isotope effects on chemical shifts are shown to be important. The magnitudes of the isotope effects are correlated both to intrinsic and equilibrium isotope effects. The latter correlate to the shape of the two-potential well, the energy difference and the difference in chemical shifts of the two tautomers.
Keywords: Secondary Deuterium Isotope Effects; Chemical Shifts; Schiff Bases; DFT Calculations; Intramolecular Hydrogen Bonding
Published Online: 2013-6-10
Published in Print: 2013-6-1
© by Oldenbourg Wissenschaftsverlag, München, Germany
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Keywords for this article
Secondary Deuterium Isotope Effects;
Chemical Shifts;
Schiff Bases;
DFT Calculations;
Intramolecular Hydrogen Bonding
Articles in the same Issue
- Editorial
- Biography of Prof. Dr. Hans-Heinrich Limbach
- Alumni and long term guests of the Limbach group
- NMR and FT-IR Studies on the Association of Derivatives of Thymidine, Adenosine, and 6-N-Methyl-Adenosine in Aprotic Solvents
- Competition between Hydrogen Bonds and Lewis Acid-Base Interactions in the Equilibria between Bis(pentafluorophenyl)borinic Acid and Pyridine: Insights from NMR, Diffractometric and Computational Studies
- Energy Analysis of Competing Non-Covalent Interaction in 1:1 and 1:2 Adducts of Collidine with Benzoic Acids by Means of X-Ray Diffraction
- A TT Dinucleotide with a Nonionic Silyl Backbone: Impact on Conformation and H-Bond Mediated Base Pairing as Studied by Low-Temperature NMR
- Oxygen and Hydrogen Isotopic Preference in Hydration Spheres of Chloride and Sulfate Ions
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- Immobilization and Characterization of RuCl2(PPh3)3 Mesoporous Silica SBA-3
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- Analysis of Nutation Patterns in Fourier-Transform NMR of Non-Thermally Polarized Multispin Systems
- The Structure of Supercooled Water and the Mechanism of Homogeneous Nucleation of Ice Ih
- Probing Small Protonated Water Clusters in Acetonitrile Solutions by 1H NMR
- Double Hydrogen Transfer in Low Symmetry Porphycenes
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