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Quantum Reality in the Selective Reduction of a Benzofuran System
Two 2,3-disubstituted benzofurans (1 and 2), analogs of gamma-aminobutyric acid (GABA), were synthesized to obtain their 2,3-dihydro derivatives from the Pd/C-driven catalytic reduction of the double bond in the furanoid ring. The synthesis produced surprising by-products. Therefore, theoretical cal...
Autores principales: | , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
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MDPI
2019
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6600454/ https://www.ncbi.nlm.nih.gov/pubmed/31151186 http://dx.doi.org/10.3390/molecules24112061 |
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author | Coaviche-Yoval, Arturo Andrade-Jorge, Erik Pérez-González, Cuauhtémoc Luna, Héctor Tovar-Miranda, Ricardo Trujillo-Ferrara, José G. |
author_facet | Coaviche-Yoval, Arturo Andrade-Jorge, Erik Pérez-González, Cuauhtémoc Luna, Héctor Tovar-Miranda, Ricardo Trujillo-Ferrara, José G. |
author_sort | Coaviche-Yoval, Arturo |
collection | PubMed |
description | Two 2,3-disubstituted benzofurans (1 and 2), analogs of gamma-aminobutyric acid (GABA), were synthesized to obtain their 2,3-dihydro derivatives from the Pd/C-driven catalytic reduction of the double bond in the furanoid ring. The synthesis produced surprising by-products. Therefore, theoretical calculations of global and local reactivity were performed based on Pearson’s hard and soft acids and bases (HSAB) principle to understand the regioselectivity that occurred in the reduction of the olefinic carbons of the compounds. Local electrophilicity (ω(k)) was the most useful parameter for explaining the selectivity of the polar reactions. This local parameter was defined with the condensed Fukui function and redefined with the electrophilic (P(k)(+)) Parr function. The similar patterns of both resulting sets of values helped to demonstrate the electrophilic behavior (soft acid) of the olefinic carbons in these compounds. The theoretical calculations, nuclear magnetic resonance, and resonance hybrids showed the moieties in each compound that are most susceptible to reduction. |
format | Online Article Text |
id | pubmed-6600454 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2019 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
spelling | pubmed-66004542019-07-16 Quantum Reality in the Selective Reduction of a Benzofuran System Coaviche-Yoval, Arturo Andrade-Jorge, Erik Pérez-González, Cuauhtémoc Luna, Héctor Tovar-Miranda, Ricardo Trujillo-Ferrara, José G. Molecules Article Two 2,3-disubstituted benzofurans (1 and 2), analogs of gamma-aminobutyric acid (GABA), were synthesized to obtain their 2,3-dihydro derivatives from the Pd/C-driven catalytic reduction of the double bond in the furanoid ring. The synthesis produced surprising by-products. Therefore, theoretical calculations of global and local reactivity were performed based on Pearson’s hard and soft acids and bases (HSAB) principle to understand the regioselectivity that occurred in the reduction of the olefinic carbons of the compounds. Local electrophilicity (ω(k)) was the most useful parameter for explaining the selectivity of the polar reactions. This local parameter was defined with the condensed Fukui function and redefined with the electrophilic (P(k)(+)) Parr function. The similar patterns of both resulting sets of values helped to demonstrate the electrophilic behavior (soft acid) of the olefinic carbons in these compounds. The theoretical calculations, nuclear magnetic resonance, and resonance hybrids showed the moieties in each compound that are most susceptible to reduction. MDPI 2019-05-30 /pmc/articles/PMC6600454/ /pubmed/31151186 http://dx.doi.org/10.3390/molecules24112061 Text en © 2019 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/). |
spellingShingle | Article Coaviche-Yoval, Arturo Andrade-Jorge, Erik Pérez-González, Cuauhtémoc Luna, Héctor Tovar-Miranda, Ricardo Trujillo-Ferrara, José G. Quantum Reality in the Selective Reduction of a Benzofuran System |
title | Quantum Reality in the Selective Reduction of a Benzofuran System |
title_full | Quantum Reality in the Selective Reduction of a Benzofuran System |
title_fullStr | Quantum Reality in the Selective Reduction of a Benzofuran System |
title_full_unstemmed | Quantum Reality in the Selective Reduction of a Benzofuran System |
title_short | Quantum Reality in the Selective Reduction of a Benzofuran System |
title_sort | quantum reality in the selective reduction of a benzofuran system |
topic | Article |
url | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6600454/ https://www.ncbi.nlm.nih.gov/pubmed/31151186 http://dx.doi.org/10.3390/molecules24112061 |
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