A Single Universal Scale of Radical Stabilization Energies Does Not Exist: Global Bond Dissociation Energies and Radical Thermochemistries Are Described by Combining Two Universal Scales-Reference-Cited by-同舟云学术

A Single Universal Scale of Radical Stabilization Energies Does Not Exist: Global Bond Dissociation Energies and Radical Thermochemistries Are Described by Combining Two Universal Scales

Published:2008-10-22 Issue:22 Volume:73 Page:9022-9026
ISSN:0022-3263
Container-title:The Journal of Organic Chemistry
language:en
Short-container-title:J. Org. Chem.

Author:

Zavitsas Andreas A.¹

Affiliation:

1. Department of Chemistry and Biochemistry, Long Island University, University Plaza, Brooklyn, New York 11201

Publisher

American Chemical Society (ACS)

Subject

Organic Chemistry

Link

https://pubs.acs.org/doi/pdf/10.1021/jo8018768

Reference28 articles.

1. THE NATURE OF THE CHEMICAL BOND. IV. THE ENERGY OF SINGLE BONDS AND THE RELATIVE ELECTRONEGATIVITY OF ATOMS

2. Pauling's Electronegativity Equation and a New Corollary Accurately Predict Bond Dissociation Enthalpies and Enhance Current Understanding of the Nature of the Chemical Bond

3. The are no resonance effects in BDE[CH2=CH–CH3] = 101.4 and BDE[CH2=CH−Cl] = 94.5 kcal mol−1. Using eq2, we obtain two equalities with two unknown values: BDE[CH2=CH−CH3] = DE[CH2=CH·] + DE[CH3·] + (ε[CH2=CH·] − ε[H3C·])2and BDE[CH2=CH−Cl] = DE[CH2=CH·] + DE[Cl·] + (ε[CH2=CH·] − ε[Cl·])2. The unknowns are DE[CH2=CH·] and ε[CH2=CH·]. Substituting the known values and solving yields ε[CH2=CH·] = 12.220 and DE[CH2=CH·] = 56.5 kcal mol− 1. The strain-free value of DE[(CH3)3C·] and ε[(CH3)3C·] are similarly obtained by assuming no significant steric strain in (CH3)3C−CH3and in (CH3)3C−Cl.

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