Doctorado en Ciencias Biológicas y de la Salud, Universidad Autónoma Metropolitana-Unidad Xochimilco, Mexico City 04960, Mexico.
Departamento de Bioquímica, Sección de Estudios de Posgrado e Investigación, Escuela Superior de Medicina, Instituto Politécnico Nacional, Mexico City 11340, Mexico.
Molecules. 2019 May 30;24(11):2061. doi: 10.3390/molecules24112061.
Two 2,3-disubstituted benzofurans ( and ), 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 () 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 () 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.
两种 2,3-二取代苯并呋喃（和）是γ-氨基丁酸（GABA）的类似物，通过 Pd/C 驱动的呋喃环双键催化还原合成了它们的 2,3-二氢衍生物。该合成产生了令人惊讶的副产物。因此，基于 Pearson 的硬软酸碱（HSAB）原理，进行了全局和局部反应性的理论计算，以了解化合物中烯烃碳的还原所发生的区域选择性。局部电负性（）是解释极性反应选择性的最有用参数。该局部参数是用凝聚的 Fukui 函数定义的，并重新定义为亲电（）Parr 函数。这两组值的相似模式有助于证明这些化合物中烯烃碳的亲电行为（软酸）。理论计算、核磁共振和共振杂化表明了每个化合物中最容易还原的部分。
