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Research And Development On Advanced Graphite Materials. Volume XVI - An Electron Spin Resonance Study Of Thermal Decomposition Reactions Of Organic Compounds

Report Number: WADD TR 61-72 Volume 16
Author: Singer, L. S.
Author: Lewis, I. C.
Corporate Author: Research Laboratory of National Carbon Company Division of Union Carbide Corporation
Laboratory: AF Materials Laboratory
Date of Publication: 1963-06
Pages: 32
Contract: AF 33(616)-6915
Project: 7350
Task: 735002
AD Number: AD0414491

Initial results of an ESR (electron spin resonance) survey of the thermal decomposition and carbonization of pure organic compounds are presented. ESR measurements were performed during pyrolysis in inert polyphenyl solvents to permit observation of resolved hyperfine structure of radical intermediates. The generality of radical formation during carbonization is demonstrated. Detailed investigations were made on the model aromatic hydrocarbons, acenaphthylene, 9,9'-bifluorenyl and 9,9'-bifluorylidene which provide examples of extremes in graphitization behavior. Results are discussed in terms of reaction mechanisms and the nature of radicals in low temperature carbons. Resolved spectra for acenaphthylene and two deuterated analogs are compared. Possible structures for the observed radicals from both acenaphthylene and the bifluorenyl-bifluorylidene system are presented and discussed theoretically in terms of the H. M O. (Hückel Molecular Orbital) method. ESR studies are reported for thermal decomposition of several aromatic diazocompounds. The observed stable radical intermediates are believed to result from further reaction of the initially generated carbene species. Detailed studies of the decomposition of diphenyl methadone suggest the presence of a radical intermediate containing the Φ2Ċ-N< grouping.

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