Products and mechanism of acene dimerization. A computational study

Journal of the American Chemical Society

Volumn 133, Issue 28, 2011, Pages 10803-10816

  Zade, Sanjio S ^a,b   Zamoshchik, Natalia ^a   Reddy, A Ravikumar ^a   Fridman Marueli, Galit ^a   Sheberla, Dennis ^a   Bendikov, Michael ^a  

^a WEIZMANN INSTITUTE OF SCIENCE   (Israel)

^b INDIAN INSTITUTE OF SCIENCE EDUCATION AND RESEARCH KOLKATA   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACTIVATION BARRIERS; BENZENE RING; CHARGE MOBILITIES; COMPUTATIONAL STUDIES; CYCLOADDITION REACTION; HIGH REACTIVITY; PENTACENES; POTENTIAL APPLICATIONS; REACTION MECHANISM; REACTION PATHWAYS; RING CLOSURES; TRANSITION STATE;

ACTIVATION ENERGY; ANTHRACENE; BENZENE; CYCLOADDITION; DIMERS; MOLECULAR ELECTRONICS; MOLECULES; NAPHTHALENE; ORGANIC FIELD EFFECT TRANSISTORS; POLYMERS;

DIMERIZATION;

ACENE DERIVATIVE; ANTHRACENE; BENZENE; CARBON; DIMER; HEPTACENE; HEXACENE; MONOMER; NAPHTHALENE; OCTACENE; PENTACENE; PHENYL GROUP; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; POLYMER; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CHEMICAL REACTION KINETICS; CYCLOADDITION; DIMERIZATION; MATHEMATICAL MODEL; MOLECULAR ELECTRONICS; POLYMERIZATION; SUBSTITUTION REACTION; TERMINAL SEQUENCE; THERMAL ANALYSIS; THERMODYNAMICS;

EID: 79960225383     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja106594v     Document Type: Article

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116. syn 1-4) that was found in the case of benzene dimerization.
117. It was suggested previously (Navarro-Vázquez, A.; Prall, M.; Schreiner, P. R. Org. Lett. 2004, 6, 2981-2984) that for Cope-type rearrangements "a nonconcerted reaction takes place when biradical intermediates are stabilized either by allyl or aromatic resonance". Anthracene and pentacene dimerizations, indeed, have a stabilized benzyl biradical intermediate and proceed via a nonconcerted pathway. However, for the dimerization of benzene and naphthalene, only a concerted pathway was found, even though the dimerization TSs have a stabilized allyl or benzyl biradical. We believe that this is because of the very high activation energies calculated for benzene and naphthalene dimerization