Additions and Corrections
596 Energy & Fuels, Vol. 2, No. 4, 1988 thiophene, which showed that an alkyl group can add to a nonhydrogen containing aromatic carbon to form a quaternary sp3-hybridized carbon. A proposal for the coupling of aromatic cation radicals with neutral radicals was expounded by H. Shine and M. Soroka. For example, the nitration reaction of aromatic compounds with NOz+ may be preceded by complete charge transfer followed by a bond-forming reaction between the aromatic radical cation and the neutral NO2 radical. D. Ross, G. Hum, and R. Schmitt presented their results on the nitration of pyrene by N02/N20, in methylene chloride, which turns out to be more effective than HN03/CHzC12. T. Richardson, F. Tanzella, and N. Bartlett discussed their results dealing with radical-cation salts of perfluoroaromatic hydrocarbons and concluded that fluoroanalogues of the metallic (C,oHs)2+ salts do not exist. The formation of a coronene-AsF, complex is described. V. Enkelmann describes his electrocrystallization synthesis of radical-cationsalts of arenes where the counterion consists of large anions like AsF,. The shiny black needles obtained were highly conductive. The occurrence of aromatic systems in petroleum and coal is well established. J. Speight discusses the evidence for the ring-size distribution in petroleum asphaltenes (pentane insoluble fraction). Using UV/HPLC, Speight concluded that since polynuclear aromatics containing four to seven rings gave signals only between 300 and 365 nm, asphaltenes contained only constituents having less than seven condensed rings and there was a preponderance of one to four ring systems. N. Berkowitz reviews the average molecular structure models for coals and suggests that these offer little to advance the understanding of coal. In the analytical investigation of solvent-refined coal liquid and coal tar by M. Nishioka and M. Lee, it was concluded that the polynuclear aromatic structures from both sources are similar. From this observation, it was suggested that the major compounds identified are either the result of similar aromatic moieties in the original coal feedstock or of processing conditions involving complex reactions that lead to similar stable final products. These investigators summarize the structural similarities of the major polynuclear species and suggest how cyclo-couplingdehydrogenation during processing may explain their origin. R. Chambers, E. Hagaman, and M. Woody used selective methylation of hydroaromatic C-H sites in bituminom coal to implicate the presence
of fluorene-like structural units. A review by I. C. Lewis and L. Singer on thermal conversion of polynuclear aromatic compounds to carbon (carbonization) discusses how large polynuclear aromatic compounds associate into a liquid crystalline state (mesophase)and further polymerize via a-radical and odd alternant *-radical intermediates. Model pyrolytic studies starting with naphthalene show that condensation commences largely with oligomerization, although species resulting from bond cleavage and molecular rearrangement are also evident in the GC and MS analyses of the resulting pitches. An interesting review on quantum-chemical-structurereactivity relationships in polycyclic benzenoid aromatic hydrocarbons is presented by L. Szentpdy and W. C. Herndon. Particular emphasis is placed on the perturbational free-electron MO method illustrated with several examples. The electronic interactions between polycyclic arenes in cyclophanes were studied by M. Haenel and D. Schweitzer, who show that this interaction was highest if a maximal number of six-membered rings were completely eclipsed in a parallel arrangement. The synthesis, chromatography, and spectrometry of 20 previously unreported polycyclic aromatic hydrocarbons by J. C. Fetzer was particularly representative of the state of the art research reported in this book. Fetzer has employed his HPLC expertise to separate and determine the structures of the Zn/ ZnC12/NaC1condensation of odd carbon ketones. M. Nagai, H. Urimoto, K. Uetake, N. Sakikawa, and R. Gonzalez, presented their results on the Raney nickel desulfurization of benzonaphthothiophenes and dibenzothiophene to give a-and @-phenylnaphthalene and biphenyl. The relative ease of desulfurization is correlated to the HMO pn-electron density on the sulfur. The culminating chapter by L. Ebert and J. Scanlon discusses the interrelation of polynuclear aromatic hydrocarbons and carbonaceous materials. The formation and reaction of the graphite intercalation compound C& occupies much of the space in this chapter. All-in-all Polynuclear Aromatic Compounds captures the current research status of benzenoid compounds in the perspective of carbonaceous materials. The book is highly recommended to all engineers and scientists working in the areas of polynuclear aromatic compounds, fossil fuels, and carbonaceous materials. Jerry Ray Dias, University of Missouri-Kansas City
Additions and Corrections Book Review by Stephen E. Stein. J. R. Dias: Handbook of Polycyclic Hydrocarbons. Part A. Benzenoid Hydrocarbons. 1988, 2, 358. Page 358. The above is t h e correct spelling of t h e author’s name. Also, t h e price of t h e book is $124.50.
