Understanding the nucleophilic character and stability of the carbanions and alkoxides of 1-(9-anthryl)ethanol and derivatives.

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.

DOI: 10.3390/molecules180910254

Cite this paper

@article{Ramrez2013UnderstandingTN, title={Understanding the nucleophilic character and stability of the carbanions and alkoxides of 1-(9-anthryl)ethanol and derivatives.}, author={Rams{\'e}s E Ram{\'i}rez and Cirilo Garc{\'i}a-Mart{\'i}nez and Francisco Javier Mart{\'i}nez M{\'e}ndez}, journal={Molecules}, year={2013}, volume={18 9}, pages={10254-65} }