Sulphuric acid-catalysed formation of hemiacetal from glyoxal and ethanol

Farzaneh Sarrami, Li Juan Yu, Wenchao Wan, Amir Karton

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)


We examine the reaction of ethanol with glyoxal to form hemiacetal by means of the high-level G4(MP2) procedure. In this reaction, an intermolecular proton transfer is coupled with the formation of a covalent C[sbnd]O bond between the two molecules. We find a novel catalytic reaction mechanism in which an H2SO4 catalyst reduces the barrier height from ∆H 298 = 140.2 to 16.3 kJ mol−1. It is well established that H2SO4 can effectively catalyse intramolecular proton transfers. This letter shows that H2SO4 can catalyse an intermolecular proton transfer that is coupled with a covalent bond formation.

Original languageEnglish
Pages (from-to)27-34
Number of pages8
JournalChemical Physics Letters
Publication statusPublished - 1 May 2017


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