Depolymerization of coals at low temperatures may offer advantages over thermal bond cleavage. Because bond cleavage energies of radical cations are lower than the corresponding homolytic bond cleavage energies of the same bond, generation of radical cations in coal may make possible depolymerization at lower temperatures. We seek to investigate the above possibility using single molecules containing functional groups common in coals. Since the generation of a radical cation requires the removal of an electron from a neutral molecule, a primary focus of the study will be finding oxidants that will remove an electron from compounds with structural similarity to those typically found in coals. The study will also be concerned with the decomposition of radical cations and the products formed as a result of the decomposition.

Following the position of the nitrile band and using the assumption that there is a linear relationship for between the extent of charge transfer and frequency, a 69% charge transfer was obtained and successfully replicates Flowers` results. If a Diels-Alder reaction occurred, we would expect the position of nitrile group to have shifted down field to the 2260-2240 cm{sup {minus}1} range for a saturated alkyl nitrile. There is no evidence for this type of reaction under these conditions since we obtained a shift upfield from 2229 cm{sup {minus}1} to 2200 cm{sup {minus}1}. There are some peaks of interest in the 1660-1300 cm{sup {minus}1} range of the deposited coals which will be investigated. The TCNE-Illinois No. 6 reaction mixture will be heated from room temperature to 180{degrees}C within the Harrick cell during IR analysis to see if a Diels-Alder or other additions reaction could occur.

The objective of this work is to investigate and characterize the single electron reactions of alkyl and alkoxy aromatic compounds in order to determine the role these reactions play in the chemistry of coal. The work here is concerned with the interactions of coals, such as Illinois No. 6, with tetracyanoethylene.