Polychlorinated biphenylenes (PCBN) from pyrolysis of chlorobenzenes: Identification and mechanism of formation

Bleise, A.; Dongmann, G.; Schlimper, H.; Günther, Klaus; Schwuger, M. J.

doi:10.1080/02772249709358454

Cited by 2 publications

(3 citation statements)

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“…With total and chlorine mass known, reasonable molecular formulas are straightforwardly obtained. Ambiguities arise as biphenylene congeners possess identical masses and exhibit mass spectra very similar to those of Cl-ACNs . Further, there is precedent in the literature where such compounds have been claimed to form in pyrolytic systems at least alongside ACN .…”

Section: Resultsmentioning

confidence: 99%

“…Ambiguities arise as biphenylene congeners possess identical masses and exhibit mass spectra very similar to those of Cl-ACNs. 93 Further, there is precedent in the literature where such compounds have been claimed to form in pyrolytic systems at least alongside ACN. 93 Evidence for preferential ACN formation is possible, however, on isomer counting.…”

Section: Introductionmentioning

confidence: 99%

“…93 Further, there is precedent in the literature where such compounds have been claimed to form in pyrolytic systems at least alongside ACN. 93 Evidence for preferential ACN formation is possible, however, on isomer counting. Only a single C 12 Cl 8 isomer is observed in our experiments and thus must be either biphenylene or ACN.…”

Section: Introductionmentioning

confidence: 99%

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High Temperature Chemistry of Chlorinated Acenaphthylene. 3C Bay Acetylene Additions and Annealing by Five-Membered Ring Shifts

McIntosh

Russell

2015

J. Phys. Chem. A

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Experimental and theoretical results concerning the growth and isomerization of chlorinated acenaphthylene, C12H8, during the pyrolysis of chlorohydrocarbons are presented here. A fullerene subunit, C12H8, is a useful system to investigate regarding C60 formation. However, direct experimental observation of isomerization and annealing processes in particular are difficult to confirm due to the high symmetry of the parent molecule. Chlorination lowers the symmetry, essentially labeling carbon atoms, allowing growth and isomerization to be followed directly. Pyrolysis of dichloro- and trichloroethylene, and their copyrolyses with trichlorobenzenes, provides an efficient and general source of chlorinated acenaphthylenes in a range of degrees of chlorination and over a number of unique congeners. Analysis of congener yields as a function of reagents employed, guided by DFT/B3LYP/6-311G(d,p) level calculations, strongly suggests that C2 addition across three-carbon bays in naphthalene is a major driver of growth. Additionally, extremely facile five-membered ring shifts are operative, with chlorine promoting isomerization. Theoretical study of C16H10- and C18H10-based congeners indicate that this is a general phenomenon, and with chlorine also favoring internal cyclopentafused rings in addition to increased isomerization rates, this suggests halogen moieties may be an important feature for efficient fullerene growth.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%