AI Article Synopsis
- The study compares the nucleophilic strength and stability of carbanions and alkoxides from two compounds: 2,2,2-trifluoro-1-(9-anthryl)ethanol and 1-(9-anthryl)ethanol, each modified with different electron-donating or withdrawing groups.
- The analysis employs advanced theoretical methods to examine various chemical properties, including acidity and nucleophilicity, to determine how these modifications influence the stability of intermediates.
- It was found that the 9-anthryl group enhances the stability of carbanions through electron delocalization, giving these compounds unique nucleophilic characteristics.
Article Abstract
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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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC6270014 | PMC |
| http://dx.doi.org/10.3390/molecules180910254 | DOI Listing |
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