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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...
Autores principales: | , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
John Wiley and Sons Inc.
2019
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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. |
format | Online Article Text |
id | pubmed-6723769 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | John Wiley and Sons Inc. |
record_format | MEDLINE/PubMed |
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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