In this work, we selected the tpss acceptor to study the interconversion reaction by replacing the pyr acceptor in (tftib)(pyr)1/2 (Eqn 1). As an initial step we theoretically predicted the enthalpy of interconversion by periodic DFT using PBE functional with two different corrections: MBD* (many-body dispersion) and Grimme D3. Positive energy values from computational results indicated that such a reaction should not proceed experimentally, and (tftib)(pyr)1/2 should remain unreacted in the resulting mixture. Finally, the dissolution calorimetry (dis-cal) measurements also revealed a positive experimental value for the reaction energy, consistent with the periodic DFT calculations (Fig. ). Conversely, the reverse reaction (Eqn 2), where (tftib)(tpss) reacts with the pyr acceptor to form the (tftib)(pyr)½ has negative calculated enthalpy (opposite value to the forward reaction), and is therefore expected to proceed experimentally. In order to verify the validity of the DFT and calorimetry predictions, milling reactions for Eqn 1 and 2 were performed by liquid-assisted grinding (LAG) with ethanol (for further experimental details see ESI). Interestingly, the experimental outcome of both forward and reverse reaction gave the reaction products, for which powder X-ray diffraction pattern (PXRD) did not match either (tftib)(pyr)1/2 or (tftib)(tpss) cocrystals. Most curiously, the PXRD patterns of the products of both forward and reverse reaction matched each other, suggesting that both reactions had lead to the formation of the same product, of yet unknown structure. The same material was subsequently obtained by mixing the three individual components (tftib), (pyr), (tpss) and milling under LAG conditions with ethanol, suggesting that the new material might be a ternary cocrystal. (see ESI Fig. ).