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Molecules 2013, 18(9), 10254-10265; doi:10.3390/molecules180910254
Article

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

1,2
, 3
 and 2,*
Received: 3 June 2013; in revised form: 13 August 2013 / Accepted: 16 August 2013 / Published: 22 August 2013
(This article belongs to the Special Issue Electrophilic & Nucleophilic Substitution)
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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.
Keywords: absolute gas phase acidity; alkoxide; carbanion; Fukui function; nucleophile absolute gas phase acidity; alkoxide; carbanion; Fukui function; nucleophile
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

Ramírez, R.E.; García-Martínez, C.; Méndez, F. Understanding the Nucleophilic Character and Stability of the Carbanions and Alkoxides of 1-(9-Anthryl)ethanol and Derivatives. Molecules 2013, 18, 10254-10265.

AMA Style

Ramírez RE, García-Martínez C, Méndez F. Understanding the Nucleophilic Character and Stability of the Carbanions and Alkoxides of 1-(9-Anthryl)ethanol and Derivatives. Molecules. 2013; 18(9):10254-10265.

Chicago/Turabian Style

Ramírez, Ramsés E.; García-Martínez, Cirilo; Méndez, Francisco. 2013. "Understanding the Nucleophilic Character and Stability of the Carbanions and Alkoxides of 1-(9-Anthryl)ethanol and Derivatives." Molecules 18, no. 9: 10254-10265.


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