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

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 ioni...

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Detalles Bibliográficos
Autores principales: Troiani, Anna, de Petris, Giulia, Pepi, Federico, Garzoli, Stefania, Salvitti, Chiara, Rosi, Marzio, Ricci, Andreina
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2019
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6723769/
https://www.ncbi.nlm.nih.gov/pubmed/31508268
http://dx.doi.org/10.1002/open.201900173
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author Troiani, Anna
de Petris, Giulia
Pepi, Federico
Garzoli, Stefania
Salvitti, Chiara
Rosi, Marzio
Ricci, Andreina
author_facet Troiani, Anna
de Petris, Giulia
Pepi, Federico
Garzoli, Stefania
Salvitti, Chiara
Rosi, Marzio
Ricci, Andreina
author_sort Troiani, Anna
collection PubMed
description 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.
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spelling pubmed-67237692019-09-10 Base‐Assisted Conversion of Protonated d‐Fructose to 5‐HMF: Searching for Gas‐Phase Green Models Troiani, Anna de Petris, Giulia Pepi, Federico Garzoli, Stefania Salvitti, Chiara Rosi, Marzio Ricci, Andreina ChemistryOpen Full Papers 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. John Wiley and Sons Inc. 2019-09-04 /pmc/articles/PMC6723769/ /pubmed/31508268 http://dx.doi.org/10.1002/open.201900173 Text en ©2019 The Authors. Published by Wiley-VCH Verlag GmbH & Co. KGaA. This is an open access article under the terms of the http://creativecommons.org/licenses/by-nc-nd/4.0/ License, which permits use and distribution in any medium, provided the original work is properly cited, the use is non‐commercial and no modifications or adaptations are made.
spellingShingle Full Papers
Troiani, Anna
de Petris, Giulia
Pepi, Federico
Garzoli, Stefania
Salvitti, Chiara
Rosi, Marzio
Ricci, Andreina
Base‐Assisted Conversion of Protonated d‐Fructose to 5‐HMF: Searching for Gas‐Phase Green Models
title Base‐Assisted Conversion of Protonated d‐Fructose to 5‐HMF: Searching for Gas‐Phase Green Models
title_full Base‐Assisted Conversion of Protonated d‐Fructose to 5‐HMF: Searching for Gas‐Phase Green Models
title_fullStr Base‐Assisted Conversion of Protonated d‐Fructose to 5‐HMF: Searching for Gas‐Phase Green Models
title_full_unstemmed Base‐Assisted Conversion of Protonated d‐Fructose to 5‐HMF: Searching for Gas‐Phase Green Models
title_short Base‐Assisted Conversion of Protonated d‐Fructose to 5‐HMF: Searching for Gas‐Phase Green Models
title_sort base‐assisted conversion of protonated d‐fructose to 5‐hmf: searching for gas‐phase green models
topic Full Papers
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6723769/
https://www.ncbi.nlm.nih.gov/pubmed/31508268
http://dx.doi.org/10.1002/open.201900173
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