Can an Amine Be a Weaker and a Stronger Base at the Same Time? Curious Cases of Chameleonic Ionization

[Image: see text] We discovered an anomalous basic dissociation in certain multiprotic compounds. An amine group placed in the middle of a given compound is predicted to behave unusually—at certain pH ranges, its averaged degree of protonation actually increases with pH (!) resulting from interactio...

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Detalles Bibliográficos
Autor principal: Fraczkiewicz, Robert
Formato: Online Artículo Texto
Lenguaje:English
Publicado: American Chemical Society 2023
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10683473/
https://www.ncbi.nlm.nih.gov/pubmed/38034037
http://dx.doi.org/10.1021/acsphyschemau.3c00029
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author Fraczkiewicz, Robert
author_facet Fraczkiewicz, Robert
author_sort Fraczkiewicz, Robert
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description [Image: see text] We discovered an anomalous basic dissociation in certain multiprotic compounds. An amine group placed in the middle of a given compound is predicted to behave unusually—at certain pH ranges, its averaged degree of protonation actually increases with pH (!) resulting from interactions with other ionizable groups. This chameleonic behavior results in two pK(50) values: one corresponding to a weaker base and the other to a stronger base for the same group.
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spelling pubmed-106834732023-11-30 Can an Amine Be a Weaker and a Stronger Base at the Same Time? Curious Cases of Chameleonic Ionization Fraczkiewicz, Robert ACS Phys Chem Au [Image: see text] We discovered an anomalous basic dissociation in certain multiprotic compounds. An amine group placed in the middle of a given compound is predicted to behave unusually—at certain pH ranges, its averaged degree of protonation actually increases with pH (!) resulting from interactions with other ionizable groups. This chameleonic behavior results in two pK(50) values: one corresponding to a weaker base and the other to a stronger base for the same group. American Chemical Society 2023-08-31 /pmc/articles/PMC10683473/ /pubmed/38034037 http://dx.doi.org/10.1021/acsphyschemau.3c00029 Text en © 2023 The Author. Published by American Chemical Society https://creativecommons.org/licenses/by/4.0/Permits the broadest form of re-use including for commercial purposes, provided that author attribution and integrity are maintained (https://creativecommons.org/licenses/by/4.0/).
spellingShingle Fraczkiewicz, Robert
Can an Amine Be a Weaker and a Stronger Base at the Same Time? Curious Cases of Chameleonic Ionization
title Can an Amine Be a Weaker and a Stronger Base at the Same Time? Curious Cases of Chameleonic Ionization
title_full Can an Amine Be a Weaker and a Stronger Base at the Same Time? Curious Cases of Chameleonic Ionization
title_fullStr Can an Amine Be a Weaker and a Stronger Base at the Same Time? Curious Cases of Chameleonic Ionization
title_full_unstemmed Can an Amine Be a Weaker and a Stronger Base at the Same Time? Curious Cases of Chameleonic Ionization
title_short Can an Amine Be a Weaker and a Stronger Base at the Same Time? Curious Cases of Chameleonic Ionization
title_sort can an amine be a weaker and a stronger base at the same time? curious cases of chameleonic ionization
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10683473/
https://www.ncbi.nlm.nih.gov/pubmed/38034037
http://dx.doi.org/10.1021/acsphyschemau.3c00029
work_keys_str_mv AT fraczkiewiczrobert cananaminebeaweakerandastrongerbaseatthesametimecuriouscasesofchameleonicionization

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