Jennifer W. Mcclaine, Xia Zhang, M. J. Wornat
Sep 15, 2006
Citations
1
Influential Citations
21
Citations
Journal
Journal of chromatography. A
Abstract
We present HPLC/UV/MS evidence to support the identification of benzo[ghi]naphtho[8,1,2-bcd]perylene as a product of supercritical toluene pyrolysis. Mass spectral data confirm that compound I-eluting in between co-eluting benzo[a]coronene/phenanthro[5,4,3,2-efghi]perylene and benzo[pqr]naphtho[8,1,2-bcd]perylene, all three of which have been unequivocally identified as C(28)H(14) products of toluene pyrolysis-is also a C(28)H(14) product component. The UV spectrum of compound I is presented, and indicates that it is a benzenoid polycyclic aromatic hydrocarbon (PAH). Five of the eight benzenoid C(28)H(14) PAH isomers have published UV spectra, and characteristics of the remaining three are deduced from annelation theory. Only one of these compounds, benzo[ghi]naphtho[8,1,2-bcd]perylene, is predicted to have a UV spectrum with characteristics that we find in the spectrum of compound I. In addition, benzo[ghi]naphtho[8,1,2-bcd]perylene is the only benzenoid C(28)H(14) isomer whose length-to-breadth ratio is consistent with the HPLC retention time of compound I. The reaction mechanism through which benzo[ghi]naphtho[8,1,2-bcd]perylene is formed in this environment is shown, and is consistent with reaction pathways of other large PAH found in this product mixture.