Evidence that alkyl substitution provides little stabilization to radicals: The C-C bond test and the nonbonded interaction contradiction

Journal of Organic Chemistry

Volumn 71, Issue 18, 2006, Pages 7045-7048

  Gronert, Scott ^a  

^a SAN FRANCISCO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DISSOCIATION; MATHEMATICAL MODELS; MOLECULAR DYNAMICS; PARAFFINS;

ALKYL SUBSTITUTION; COMPUTATIONAL DATA; NONBONDED INTERACTIONS;

CHEMICAL BONDS;

ALKANE DERIVATIVE; ALKYL GROUP; CARBON; HYDROGEN;

ARTICLE; CALCULATION; CHEMICAL BOND; DISSOCIATION; ENERGY; MATHEMATICAL MODEL; MEASUREMENT; MOLECULAR INTERACTION; STEREOCHEMISTRY; SUBSTITUTION REACTION;

EID: 33750432838     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo060797y     Document Type: Article

References (38)

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37. One could fit the equations by allowing BE to be a variable (while setting the NB terms to a single, constant value), but the available data would require that BE balance the changes in RS (i.e., alkyl substitution would provide nearly equal stabilization to the radical and parent alkane and, therefore, have only a minor effect on the dissociation energy). In any case, allowing BE to be a variable eliminates any possibility of equating BDEs with radical stabilization energies.
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