Base‐Assisted Conversion of Protonated D‐Fructose to 5‐HMF: Searching for Gas‐Phase Green Models

Autor: Dr. Anna Troiani, Prof. Dr. Giulia de Petris, Prof. Dr. Federico Pepi, Dr. Stefania Garzoli, Dr. Chiara Salvitti, Prof. Dr. Marzio Rosi, Prof. Dr. Andreina Ricci
Jazyk: angličtina
Rok vydání: 2019
Předmět:
Zdroj: ChemistryOpen, Vol 8, Iss 9, Pp 1190-1198 (2019)
Druh dokumentu: article
ISSN: 2191-1363
DOI: 10.1002/open.201900173
Popis: Abstract A gas‐phase investigation of the D‐fructose dehydration reaction in the presence of base has been performed by the joint application of mass spectrometric techniques and theoretical calculations. Protonated addition products of D‐fructose and base were generated in the gas phase by electrospray ionization using several bases of different proton affinity. The intermediates, products and decomposition channels were investigated by ion trap mass spectrometry. Electronic structure calculations allowed the identification of the ionic intermediates and products of a selected system containing NH3, helping to rationalize the observed reaction pathways. The obtained results show that the final product, the protonated 5‐hydroxymethyl‐2‐furaldheyde [5‐HMF]H+, is better formed using selected bases and only if these remain clustered until the end of the dehydration process.
Databáze: Directory of Open Access Journals
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