Understanding the Nucleophilic Character and Stability of the Carbanions and Alkoxides of 1-(9-Anthryl)ethanol and Derivatives

The nucleophilic character and stability of the carbanions vs. alkoxides derived from 2,2,2-trifluoro-1-(9-anthryl)ethanol and 1-(9-anthryl)ethanol containing X electron-releasing and X electron-acceptor substituents attached to C-10, have been studied at the B3LYP/6-31+G(d,p) level of theory. Resul...

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Autores principales: Ramírez, Ramsés E., García-Martínez, Cirilo, Méndez, Francisco
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2013
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270014/
https://www.ncbi.nlm.nih.gov/pubmed/23973997
http://dx.doi.org/10.3390/molecules180910254
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author Ramírez, Ramsés E.
García-Martínez, Cirilo
Méndez, Francisco
author_facet Ramírez, Ramsés E.
García-Martínez, Cirilo
Méndez, Francisco
author_sort Ramírez, Ramsés E.
collection PubMed
description The nucleophilic character and stability of the carbanions vs. alkoxides derived from 2,2,2-trifluoro-1-(9-anthryl)ethanol and 1-(9-anthryl)ethanol containing X electron-releasing and X electron-acceptor substituents attached to C-10, have been studied at the B3LYP/6-31+G(d,p) level of theory. Results analyzed in terms of the absolute gas-phase acidity, Fukui function, the local hard and soft acids and bases principle, and the molecular electrostatic potential, show that the central ring of the 9-anthryl group confers an ambident nucleophilic character and stabilizes the conjugated carbanion by electron-acceptor delocalization.
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spelling pubmed-62700142018-12-18 Understanding the Nucleophilic Character and Stability of the Carbanions and Alkoxides of 1-(9-Anthryl)ethanol and Derivatives Ramírez, Ramsés E. García-Martínez, Cirilo Méndez, Francisco Molecules Article The nucleophilic character and stability of the carbanions vs. alkoxides derived from 2,2,2-trifluoro-1-(9-anthryl)ethanol and 1-(9-anthryl)ethanol containing X electron-releasing and X electron-acceptor substituents attached to C-10, have been studied at the B3LYP/6-31+G(d,p) level of theory. Results analyzed in terms of the absolute gas-phase acidity, Fukui function, the local hard and soft acids and bases principle, and the molecular electrostatic potential, show that the central ring of the 9-anthryl group confers an ambident nucleophilic character and stabilizes the conjugated carbanion by electron-acceptor delocalization. MDPI 2013-08-22 /pmc/articles/PMC6270014/ /pubmed/23973997 http://dx.doi.org/10.3390/molecules180910254 Text en © 2013 by the authors; licensee MDPI, Basel, Switzerland. http://creativecommons.org/licenses/by/3.0/ This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution license (http://creativecommons.org/licenses/by/3.0/).
spellingShingle Article
Ramírez, Ramsés E.
García-Martínez, Cirilo
Méndez, Francisco
Understanding the Nucleophilic Character and Stability of the Carbanions and Alkoxides of 1-(9-Anthryl)ethanol and Derivatives
title Understanding the Nucleophilic Character and Stability of the Carbanions and Alkoxides of 1-(9-Anthryl)ethanol and Derivatives
title_full Understanding the Nucleophilic Character and Stability of the Carbanions and Alkoxides of 1-(9-Anthryl)ethanol and Derivatives
title_fullStr Understanding the Nucleophilic Character and Stability of the Carbanions and Alkoxides of 1-(9-Anthryl)ethanol and Derivatives
title_full_unstemmed Understanding the Nucleophilic Character and Stability of the Carbanions and Alkoxides of 1-(9-Anthryl)ethanol and Derivatives
title_short Understanding the Nucleophilic Character and Stability of the Carbanions and Alkoxides of 1-(9-Anthryl)ethanol and Derivatives
title_sort understanding the nucleophilic character and stability of the carbanions and alkoxides of 1-(9-anthryl)ethanol and derivatives
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270014/
https://www.ncbi.nlm.nih.gov/pubmed/23973997
http://dx.doi.org/10.3390/molecules180910254
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