Various model compounds, representative of aromatic structures found in coal liquefaction, were synthesized and tested for their stability and reactivity with hydrogen donor molecules at typical liquefaction conditions. Dibenzophenanthrene was found too difficult to synthesize but led to the finding that dihydrodibenzophenanthrene, a high yield co-product, is an attractive candidate for ranking hydrogen donors. Reactions of o-terphenyl with hydrogen donors were analyzed kinetically and found to be pseudo-first order. Biphenyl in the cleavage products was used as a measure of hydrogen donor effectiveness, although the reactive form of the donor is apparently a radical, present in low steady state concentrations. Binaphthyl reacted with various hydrogen donors to yield the completed product, perylene. The simplicity of the product slate indicated a minimum of free radical species, and allowed potential coal-derived H-donors to be ranked for their efficiency in promoting reactions. Several model biaromatic compounds with the potential of coupling into new exceptionally stable six-membered aromatic rings were shown to do so in significant yields at the 400 to 470/sup 0/C. The use of added 1,1'-binaphthyl to a potential coal-derived H-donor was shown as a way to analyze the potential H-donor for its relative ability to donate hydrogen. The order was found to be quite similar to results with the same H-donors used in actual liquefaction, showing this method to be an effective way to quantitatively compare H-donor solvents. The resulting molecules had much lower solubility and higher melting points, making them more difficult to analyze than their precursors. The implications to coal liquefaction are enormous if there are biaromatic linkages in any of the coal fragments as they degrade to lower molecular weight species. 7 refs.