Comparison between intramolecular proton transfers involving the carboxylate and alkoxide groups

Enric Bosch, Miquel Moreno, José M. Lluch, Juan Bertrán

Research output: Contribution to journalArticleResearchpeer-review

15 Citations (Scopus)

Abstract

We have studied the intramolecular proton transfer in the hydroxyacetate, hydrogenoxalate and glycolate anions by means of ab initio calculations. Due to the higher proton affinity of RO- as compared to R-COO-, there is only one minimum in the hydroxyacetate potential surface. Conversely, given that hydrogenoxalate and glycolate anions are symmetric systems, a transition state appears in both cases. The greater barrier in the hydrogenoxalate with respect to the glycolate anion can be attributed to the reorganisation energy of the substrate. The proton motion in the hydrogenoxalate molecule is clearly coupled to the motion of the other atoms. © 1990.
Original languageEnglish
Pages (from-to)77-83
JournalChemical Physics
Volume148
DOIs
Publication statusPublished - 15 Nov 1990

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