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

作者：Ramirez Ramses E; Garcia Martinez Cirilo; Mendez Francisco^*

来源：Molecules, 2013, 18(9): 10254-10265.

DOI：10.3390/molecules180910254

• absolute gas phase acidity
• alkoxide
• carbanion
• Fukui function
• nucleophile

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.

• 出版日期2013-9