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

ChemistryOpen

Dr. Anna Troiani¹  Dr. Stefania Garzoli¹  Prof. Dr. Federico Pepi¹  Dr. Chiara Salvitti¹  Prof. Dr. Giulia de Petris¹  Prof. Dr. Marzio Rosi²  Prof. Dr. Andreina Ricci³ 

[1] Department of Chemistry and Drug Technologies ‘Sapienza' University of Rome P.le A. Moro 5 00185 Rome Italy;Department of Civil and Environmental Engineering and CNR-ISTM University of Perugia Via Duranti 93 06125 Perugia Italy;Department of Math. and Phys. University of Campania L. Vanvitelli Viale Lincoln 5 81100 Caserta Italy;

关键词: green chemistry;    density functional calculations;    gas-phase reactions;    mass spectrometry;    reactions mechanism;   

DOI  :  10.1002/open.201900173

来源: DOAJ

【 摘 要 】

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.

【 授权许可】

Unknown