Stabilization of N-, N,N-, N,N'-Methylated and Unsubstituted Simple Amidine Salts by Multifurcated Hydrogen Bonds

Jaroslaw Spychala

doi:https://doi.org/10.1155/2006/589273

Stabilization of N-, N,N-, N,N'-Methylated and Unsubstituted Simple Amidine Salts by Multifurcated Hydrogen Bonds

Abstract

In the light of the usefulness of amidines in medicinal chem., this paper considers the effects on biol. properties and chem. reactivities of org. mols. affected by intramol. interactions. The study of chem. shifts has been an important source of information on the electronic structure of amidine salts and their ability to form non-covalent bonds with nucleic acids. The NMR and IR results demonstrate that hydrogen bonds are a force for promoting chem. reactions. The thymine O2 carbonyl oxygen in a close proximity to the amidinium cation does interact with the appropriately spaced amidinium NH donor moieties. The 1H-15N 2D NMR (GHSQC and GHMBC) spectra with natural isotopic abundance of 15N fully confirm the intramol. character of the bonds. A rule able to est. the relative strength of the new multifurcated hydrogen bonds is given. The appearance of the ΔδNH chem. shift differences near zero is due to the strong intramol. interactions. The strength of the H-bond donation by acetamidines is reflected in the N-H dissocn./recombination process (pos. charge shift has been invoked to explain other effects on benzamidines). The temp. dependence of chem. shift for the amidine NH protons in DMSO solns. is herein discussed.

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Jaroslaw Spychala dr

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Category:: Magazine publication
Type:: Magazine publication
Published in:: Journal of Spectroscopy no. 20, edition 4, pages 169 - 176,
ISSN: 2314-4920
Publication year:: 2006
Bibliographic description:: Jaroslaw Spychala, Stabilization of N-, N,N-, N,N'-Methylated and Unsubstituted Simple Amidine Salts by Multifurcated Hydrogen Bonds, Spectroscopy, vol. 20(4), pages169-176, 2006.
DOI:: Digital Object Identifier (open in new tab) https://doi.org/10.1155/2006/589273
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