Quantum Reality in the Selective Reduction of a Benzofuran System
Two 2,3-disubstituted benzofurans (<b>1</b> and <b>2</b>), 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 b...
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| Format: | Article |
| Language: | English |
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MDPI AG
2019-05-01
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| Series: | Molecules |
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| Online Access: | https://www.mdpi.com/1420-3049/24/11/2061 |
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| author | Arturo Coaviche-Yoval Erik Andrade-Jorge Cuauhtémoc Pérez-González Héctor Luna Ricardo Tovar-Miranda José G. Trujillo-Ferrara |
| author_facet | Arturo Coaviche-Yoval Erik Andrade-Jorge Cuauhtémoc Pérez-González Héctor Luna Ricardo Tovar-Miranda José G. Trujillo-Ferrara |
| author_sort | Arturo Coaviche-Yoval |
| collection | DOAJ |
| description | Two 2,3-disubstituted benzofurans (<b>1</b> and <b>2</b>), 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 (<b>ω<i><sub>k</sub></i></b>) 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 (<b><i>P<sub>k</sub><sup>+</sup></i></b>) 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. |
| first_indexed | 2024-12-22T13:36:06Z |
| format | Article |
| id | doaj.art-532149f3cb2c4d80a5c92fc5d1ec6117 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-22T13:36:06Z |
| publishDate | 2019-05-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-532149f3cb2c4d80a5c92fc5d1ec61172022-12-21T18:24:02ZengMDPI AGMolecules1420-30492019-05-012411206110.3390/molecules24112061molecules24112061Quantum Reality in the Selective Reduction of a Benzofuran SystemArturo Coaviche-Yoval0Erik Andrade-Jorge1Cuauhtémoc Pérez-González2Héctor Luna3Ricardo Tovar-Miranda4José G. Trujillo-Ferrara5Doctorado en Ciencias Biológicas y de la Salud, Universidad Autónoma Metropolitana-Unidad Xochimilco, Mexico City 04960, MexicoDepartamento de Bioquímica, Sección de Estudios de Posgrado e Investigación, Escuela Superior de Medicina, Instituto Politécnico Nacional, Mexico City 11340, MexicoDepartamento de Sistemas Biológicos, Universidad Autónoma Metropolitana-Unidad Xochimilco, Mexico City 04960, MexicoDepartamento de Sistemas Biológicos, Universidad Autónoma Metropolitana-Unidad Xochimilco, Mexico City 04960, MexicoInstituto de Ciencias Básicas, Universidad Veracruzana, Xalapa 91190, Veracruz, MexicoDepartamento de Bioquímica, Sección de Estudios de Posgrado e Investigación, Escuela Superior de Medicina, Instituto Politécnico Nacional, Mexico City 11340, MexicoTwo 2,3-disubstituted benzofurans (<b>1</b> and <b>2</b>), 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 (<b>ω<i><sub>k</sub></i></b>) 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 (<b><i>P<sub>k</sub><sup>+</sup></i></b>) 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.https://www.mdpi.com/1420-3049/24/11/2061catalytic reductionolefinic carbonsselectivityglobal reactivitylocal reactivityelectrophilic |
| spellingShingle | Arturo Coaviche-Yoval Erik Andrade-Jorge Cuauhtémoc Pérez-González Héctor Luna Ricardo Tovar-Miranda José G. Trujillo-Ferrara Quantum Reality in the Selective Reduction of a Benzofuran System Molecules catalytic reduction olefinic carbons selectivity global reactivity local reactivity electrophilic |
| 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 | catalytic reduction olefinic carbons selectivity global reactivity local reactivity electrophilic |
| url | https://www.mdpi.com/1420-3049/24/11/2061 |
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