title: 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.
authors: 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.
authors: Ramsés E
authors: RE
authors: Ramírez
authors: Cirilo
authors: C
authors: García-Martínez
authors: Francisco
authors: F
authors: Méndez
mesh_terms: D000838:Anions / Q000737:chemistry; D000873:Anthracenes / Q000737:chemistry*; D004355:Drug Stability; D004563:Electrochemistry; D008956:Models, Chemical; D011789:Quantum Theory; D013816:Thermodynamics; D014270:Trifluoroethanol / Q000031:analogs & derivatives* / Q000737:chemistry
chemical_list: D000838:Anions; D000873:Anthracenes; C090817:2,2,2-trifluoro-1-(9-anthryl)ethanol; D014270:Trifluoroethanol
references: Chirality. 2003 Mar;15(3):256-70
references: 12582993
references: J Phys Chem A. 2005 Apr 28;109(16):3717-21
references: 16839039
references: Org Lett. 2001 Nov 15;3(23):3643-6
references: 11700102
references: J Mol Model. 2012 May;18(5):2175-84
references: 21947446
references: Org Lett. 2004 May 27;6(11):1781-3
references: 15151413
references: J Am Chem Soc. 2004 Feb 18;126(6):1716-25
references: 14871102
references: J Phys Chem A. 2009 Oct 8;113(40):10753-8
references: 19751060
references: J Am Chem Soc. 2007 Aug 8;129(31):9753-61
references: 17636911