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In this study, variations in the free radical concentration, degree of swelling (Q), and extraction yield of Buertai coal (C%, 80.4%) in 11 solvents with different characteristics were determined to investigate the interaction between the coal and solvent, as well as the bond cleavage during solvent extraction. Derivative thermogravimetry (DTG) results for the residues and raw coal were compared to confirm whether the covalent bond breaks during solvent extraction. The free radical concentration decreases in certain solvents but increases in a few others. The relative free radical concentration, Q, and extraction yield are positively correlated. The charge-transfer capability of the solvent, and in particular its electron-donating capability, plays an essential role in influencing the interaction between the coal and solvent. The increase in the free radical concentration during solvent extraction can be attributed to (1) the formation or decomposition of charge-transfer complexes, (2) dissociation of charge-transfer complexes into radical ions, and (3) breakage of weak covalent bonds. DTG results show the occurrence of weak covalent bonds breakage at temperatures of 133.9−320.1 °C during solvent extraction due to the reduction of the bond energy caused by the formation of radical ions.