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

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

1
Departamento de Fisicomatemáticas, Facultad de Ciencias Químicas, Av. San Claudio y 14 Sur, Col. San Manuel, Benemérita Universidad Autónoma de Puebla, C.P. 72570, Puebla, Pue., Mexico
2
Departamento de Química, División de Ciencias Básicas e Ingeniería, Universidad Autónoma Metropolitana-Iztapalapa, A.P. 55-534, México, D. F., 09340 Mexico
3
Química, Departamento de Ciencias Básicas, Universidad Autónoma Metropolitana-Azcapotzalco, San Pablo #180, Col. Reynosa, México, D. F., 02200 Mexico
*
Author to whom correspondence should be addressed.
Received: 3 June 2013 / Revised: 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
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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.

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