Hydrogen atom or proton transfer in neutral and single positive ions of salicylic acid and related compounds

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Abstract

The nature of the process 'hydrogen atom' or 'proton' transfer reaction in neutral and single positive ions of salicylic acid, o-hydroxybenzaldehyde, and salicylaldimine has been studied using the B3LYP density functional method. Single-point calculations at the CCSD(T) level have also been performed. For neutral systems, the reaction corresponds to a proton transfer process coupled with an important electronic transfer, which leads to a compound with nonzwitterionic character. A similar behavior is observed for ionized π radical cations. In ionized σ states, however, the process is that of a hydrogen transfer. In all cases, π ionization strengthens the initial H-bond and favors the reaction. For some of the systems the proton transfer occurs spontaneously.
Original languageEnglish
Pages (from-to)8882-8890
JournalJournal of the American Chemical Society
Volume121
Issue number38
DOIs
Publication statusPublished - 29 Sep 1999

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