Correlating acidities, electron affinities, and bond dissociation energies. Measure one, get all three!

Journal of Organic Chemistry

Volumn 69, Issue 26, 2004, Pages 9176-9183

  Fattahi, Alireza ^a   Kass, Steven R ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACIDITY; CARBOXYLIC ACIDS; DATA REDUCTION; DISSOCIATION; THERMODYNAMICS;

BOND ENERGY; ELECTRON AFFINITY; HYBRIDIZATION; THERMODYNAMIC CYCLE;

CHEMICAL BONDS;

ALCOHOL DERIVATIVE; CARBOXYLIC ACID DERIVATIVE;

ACIDITY; ARTICLE; BINDING AFFINITY; CHEMICAL BOND; DISSOCIATION; ELECTRON TRANSPORT; ENERGY; ENTHALPY; HYBRIDIZATION; THERMODYNAMICS;

EID: 10844241549     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0488964     Document Type: Article

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38. 2 is partially localized and partially delocalized, and the aromatic ring is conjugated to the double bond in the acid but to the charge center in the anion. Phenylcyclopropane could be viewed similarly, but conjugation is more important in the anion and less important in the acid as indicated by the B3LYP/6-31+G(d) rotational barriers. The inversion barrier in the anion also is smaller, so phenylcyclopropane was retained in the statistical analysis. Benzocyclopropene and dihydropentadiene also are included in the data analysis despite large experimental uncertainties because excluding them does not change the results.
39. 19 anion in the delocalized carbanion data set.
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41. -).
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