The blandly coordinating reactants proline (Figure ), 1,1′-bi-2-naphthol (BINOL, Figure ) or ephedrine (Figure ) did not show any or negligible variation in the sublimation speed of D-(+)-Cph upon inclusion of one or the other enantiomer additive. On the other hand, the use of the substituted chiral thiourea THU (Figure ) did result in a markedly faster and linear sublimation of D-(+)-Cph when the R species was used and a slowed evolution of the analyte vapor in case of the opposite enantiomer. This difference in behavior was additionally confirmed by four cross-experiments involving the possible combinations of camphor (D-(+) and L-(-)) and thiourea additive (R and S). Furthermore, it was evaluated on the base of the total Cph sublimate collected over 120 minutes with the same setup used to collect fraction of TLA in the previous part of the work. When "favorable" combinations of camphor and THU were milled, a higher amount (14-18 mg) of analyte condensed in the trap, while upon using "unfavorable" mixtures of THU and Cph only a lower mass of analyte (8-9 mg) was collectable. It was also visually possible (Figure 27, S9) to distinguish between the two types of Cph-THU combinations from the residue in the jar at the end of the reaction: a sticky consistency formed when an "unfavorable" combination of the two solids was ground, thus tampering the release of Cph to the gaseous phase. Such behavior can be explained with the formation of a liquid compound when camphor is combined with only one of the two enantiomers of the additive, similarly to what was reported for combinations of D-(+)-camphor with (1S,2S)-pseudoephedrine (solid co-crystal) or (1R,2S)-ephedrine (liquid mixture) which only differed in one stereocenter. In case of "favorable" Cph-THU combinations, the consistency of the mixture remained powdery, allowing a free sublimation of the analyte.