Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5375760 | Chemical Physics | 2009 | 8 Pages |
Abstract
Results indicate that the protonation of pyridine nitrogen promotes the enolimine-ketoenamine tautomerism. The importance of pyridine nitrogen on the “electron-sink” effect in the carbanionic molecules clearly depends on the protonation state of the imine nitrogen: in the enolimine tautomers, where the imine nitrogen is deprotonated, a 70% of the electron charge is delocalized on the pyridine ring, whereas in the ketoenamine type structures, where the imine nitrogen is fully protonated, just a 20% of this charge is delocalized in this molecular moiety. The results are discussed in relation to the chemistry of some PLP-dependent enzymes and the structure of their active sites.
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Authors
Rodrigo Casasnovas, Antoni Salvà , Juan Frau, Josefa Donoso, Francisco Muñoz,