Resonance stabilization energies in polycyclic aromatic hydrocarbon

Journal Article · Fri Mar 04 04:00:00 EST 1977 · J. Org. Chem.; (United States)

DOI:https://doi.org/10.1021/jo00425a015· OSTI ID:7323621

Stein, S E; Golden, D M

It is shown that relative values of ..pi..-bonding resonance stabilization energies for benzyl-type polycyclic aromatic radicals, as calculated by SCF-MO methods, closely correspond to energies calculated by the simple resonance theory approach of Herndon. The formula derived for the latter type of ..pi..-bonding resonance stabilization energy is E/sub ..pi..RSE/ (kcal mole/sup -1/) = 22.68 ln (CSC(R.)) -27.33 ln (CSC(RH)), where CSC(R.) and CSC(RH) are the corrected structure counts (number of stable Kekule isomers) for the radical and parent molecule, respectively. Two methods are then suggested for modifying this formula to estimate empirical radical stabilization energies for use in predicting standard heats of formation of stabilized hydrocarbon radicals.

• Research Organization: Stanford Research Inst., Menlo Park, CA
• OSTI ID: 7323621
• Journal Information: J. Org. Chem.; (United States), Journal Name: J. Org. Chem.; (United States) Vol. 42:5; ISSN JOCEA
• Country of Publication: United States
• Language: English

Related Subjects

37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
400301* -- Organic Chemistry-- Chemical & Physicochemical Properties-- (-1987)
AROMATICS
CALCULATION METHODS
ENTHALPY
EQUATIONS
FORMATION HEAT
HYDROCARBONS
MATHEMATICAL MODELS
MOLECULAR MODELS
ORGANIC COMPOUNDS
PHYSICAL PROPERTIES
POLYCYCLIC AROMATIC HYDROCARBONS
PREDICTION EQUATIONS
REACTION HEAT
SELF-CONSISTENT FIELD
THERMODYNAMIC PROPERTIES