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.

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.