Tetracyanoethylene (TCNE) and Tetracyanoquinodimethane (TCNQ) were used earlier in an attempt to determine the single electron donating ability of aromatic groups in coals. The extent of electron transfer from coals to these compounds was measured by determining the frequency shift of the nitrile stretching bands in the Diffuse Reflectance (DR) infrared spectra. Our addition to this work will be to study the interactions of coals, such as Illinois No. 6, with TCNE. We will determine whether a Diels-Alder reaction or other addition reactions are occurring.

Radical cation generation in coal may make possible depolymerization at low temperature. This possibility was investigated using single molecules containing functional groups common in coals. Single- electron oxidations of 4,4{prime}-dimethoxybibenzyl (DMBB) by Fe(III) (1,10-phenanthroline){sub 3}(ClO{sub 4}){sub 3}, in refluxing CH{sub 3}CN, gave incomplete mass balances; an attempt was made to identify the additional products. Part of these products were deduced to be dimer, p-methoxybenzylated dimer of DMBB; mono, di, and tri-p- methoxybenzylated DMBB. Similar oxidations in CH{sub 2}Cl{sub 2} and sulfolane solvents gave similar results. Attempts to use other solvents were unsuccessful.