Can carbonic acid protonate biological bases? Support from base protonation in methanol solvent
In separate contributions, we have focussed on demonstrating that carbonic acid (CA) - historically considered too unstable to be a viable protonating agent - is able to protonate several types of pH indicators while behaving as a regular, moderately strong, carboxylic acid. Together with the experi...
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ftunivnantes:oai:HAL:hal-04005994v1 2023-05-15T15:52:30+02:00 Can carbonic acid protonate biological bases? Support from base protonation in methanol solvent Aminov, Daniel Pines, Dina Philip, M. Kiefer Daschakraborty, Snehasis James, T. Hynes Pines, Ehud Processus d'Activation Sélective par Transfert d'Energie Uni-électronique ou Radiatif (UMR 8640) (PASTEUR) Département de Chimie - ENS Paris École normale supérieure - Paris (ENS-PSL) Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-École normale supérieure - Paris (ENS-PSL) Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS) 2019 https://hal-ens.archives-ouvertes.fr/hal-04005994 https://doi.org/10.1051/epjconf/201920509005 en eng HAL CCSD EDP Sciences info:eu-repo/semantics/altIdentifier/doi/10.1051/epjconf/201920509005 hal-04005994 https://hal-ens.archives-ouvertes.fr/hal-04005994 doi:10.1051/epjconf/201920509005 ISSN: 2100-014X EPJ Web of Conferences https://hal-ens.archives-ouvertes.fr/hal-04005994 EPJ Web of Conferences, 2019, 205, pp.09005. ⟨10.1051/epjconf/201920509005⟩ [CHIM]Chemical Sciences info:eu-repo/semantics/article Journal articles 2019 ftunivnantes https://doi.org/10.1051/epjconf/201920509005 2023-03-08T00:47:03Z In separate contributions, we have focussed on demonstrating that carbonic acid (CA) - historically considered too unstable to be a viable protonating agent - is able to protonate several types of pH indicators while behaving as a regular, moderately strong, carboxylic acid. Together with the experimental support we found for considering CA as a regular carboxylic acid are theoretical calculations demonstrating CA’s ability to protonate methylamine within 25 fs when forming with it a contact reactive complex. Here we briefly discuss a further aspect of this focus, involving the measurement of the lifetime and pKa of CA in pure methanol. The lifetime in methanol was found to be about 12-fold longer than in water, showing that the decomposition reaction of CA is solvent-dependent. The pKa change upon transferring CA from water to methanol was found to be 4.7 ± 0.1 pKa units, changing from 3.49 ± 0.03 to 8.16 ± 0.05: this change is similar to the pKa change observed for common stable carboxylic acids when these are transferred from water to methanol. These results add further support of our earlier proposal that CA can be an important protonating agent of biological bases in the blood plasma. Article in Journal/Newspaper Carbonic acid Université de Nantes: HAL-UNIV-NANTES EPJ Web of Conferences 205 09005 |
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Université de Nantes: HAL-UNIV-NANTES |
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ftunivnantes |
language |
English |
topic |
[CHIM]Chemical Sciences |
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[CHIM]Chemical Sciences Aminov, Daniel Pines, Dina Philip, M. Kiefer Daschakraborty, Snehasis James, T. Hynes Pines, Ehud Can carbonic acid protonate biological bases? Support from base protonation in methanol solvent |
topic_facet |
[CHIM]Chemical Sciences |
description |
In separate contributions, we have focussed on demonstrating that carbonic acid (CA) - historically considered too unstable to be a viable protonating agent - is able to protonate several types of pH indicators while behaving as a regular, moderately strong, carboxylic acid. Together with the experimental support we found for considering CA as a regular carboxylic acid are theoretical calculations demonstrating CA’s ability to protonate methylamine within 25 fs when forming with it a contact reactive complex. Here we briefly discuss a further aspect of this focus, involving the measurement of the lifetime and pKa of CA in pure methanol. The lifetime in methanol was found to be about 12-fold longer than in water, showing that the decomposition reaction of CA is solvent-dependent. The pKa change upon transferring CA from water to methanol was found to be 4.7 ± 0.1 pKa units, changing from 3.49 ± 0.03 to 8.16 ± 0.05: this change is similar to the pKa change observed for common stable carboxylic acids when these are transferred from water to methanol. These results add further support of our earlier proposal that CA can be an important protonating agent of biological bases in the blood plasma. |
author2 |
Processus d'Activation Sélective par Transfert d'Energie Uni-électronique ou Radiatif (UMR 8640) (PASTEUR) Département de Chimie - ENS Paris École normale supérieure - Paris (ENS-PSL) Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-École normale supérieure - Paris (ENS-PSL) Université Paris sciences et lettres (PSL)-Université Paris sciences et lettres (PSL)-Institut de Chimie du CNRS (INC)-Sorbonne Université (SU)-Centre National de la Recherche Scientifique (CNRS) |
format |
Article in Journal/Newspaper |
author |
Aminov, Daniel Pines, Dina Philip, M. Kiefer Daschakraborty, Snehasis James, T. Hynes Pines, Ehud |
author_facet |
Aminov, Daniel Pines, Dina Philip, M. Kiefer Daschakraborty, Snehasis James, T. Hynes Pines, Ehud |
author_sort |
Aminov, Daniel |
title |
Can carbonic acid protonate biological bases? Support from base protonation in methanol solvent |
title_short |
Can carbonic acid protonate biological bases? Support from base protonation in methanol solvent |
title_full |
Can carbonic acid protonate biological bases? Support from base protonation in methanol solvent |
title_fullStr |
Can carbonic acid protonate biological bases? Support from base protonation in methanol solvent |
title_full_unstemmed |
Can carbonic acid protonate biological bases? Support from base protonation in methanol solvent |
title_sort |
can carbonic acid protonate biological bases? support from base protonation in methanol solvent |
publisher |
HAL CCSD |
publishDate |
2019 |
url |
https://hal-ens.archives-ouvertes.fr/hal-04005994 https://doi.org/10.1051/epjconf/201920509005 |
genre |
Carbonic acid |
genre_facet |
Carbonic acid |
op_source |
ISSN: 2100-014X EPJ Web of Conferences https://hal-ens.archives-ouvertes.fr/hal-04005994 EPJ Web of Conferences, 2019, 205, pp.09005. ⟨10.1051/epjconf/201920509005⟩ |
op_relation |
info:eu-repo/semantics/altIdentifier/doi/10.1051/epjconf/201920509005 hal-04005994 https://hal-ens.archives-ouvertes.fr/hal-04005994 doi:10.1051/epjconf/201920509005 |
op_doi |
https://doi.org/10.1051/epjconf/201920509005 |
container_title |
EPJ Web of Conferences |
container_volume |
205 |
container_start_page |
09005 |
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1766387669350219776 |