Open AccessBase‐Assisted Conversion of Protonated D ‐Fructose to 5‐HMF: Searching for Gas‐Phase Green Models
Author(s) -
Troiani Anna,
de Petris Giulia,
Pepi Federico,
Garzoli Stefania,
Salvitti Chiara,
Rosi Marzio,
Ricci Andreina
Publication year - 2019
Publication title -
chemistryopen
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.644
H-Index - 29
ISSN - 2191-1363
DOI - 10.1002/open.201900173
Subject(s) - chemistry , protonation , electrospray ionization , mass spectrometry , proton affinity , base (topology) , ionic bonding , hydroxymethyl , dehydration , dehydration reaction , fructose , ion , chromatography , organic chemistry , biochemistry , mathematical analysis , mathematics
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 NH 3 , 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.