1. Base‐Assisted Conversion of Protonated d‐Fructose to 5‐HMF: Searching for Gas‐Phase Green Models
- Author
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Federico Pepi, Stefania Garzoli, Marzio Rosi, Chiara Salvitti, Anna Troiani, Andreina Ricci, Giulia de Petris, Troiani, Anna, Giulia de Petri, Federico Pepi, Stefania Garzoli, Chiara Salvitti, Marzio Rosi, and Ricci, Andreina
- Subjects
Green chemistry ,gas-phase reactions ,Electrospray ionization ,Ionic bonding ,Protonation ,010402 general chemistry ,Mass spectrometry ,01 natural sciences ,lcsh:Chemistry ,Computational chemistry ,mass spectrometry ,masss spectrometry, theoretical calculations, fructose dehydration, gas-phase ,Full Paper ,010405 organic chemistry ,Chemistry ,green chemistry ,General Chemistry ,Full Papers ,Decomposition ,0104 chemical sciences ,lcsh:QD1-999 ,Dehydration reaction ,density functional calculations ,reactions mechanism ,Proton affinity - 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.
- Published
- 2019