ABSTRACT
For the first time, four series of new phthalide-containing heteroaromatic compounds were separated by reverse phase HPLC: OYO, OYS, SYS; OYOYO, OYOYS, SYOYS; SYSYS, SYSYO, OYSYO; OYYO, OYYS, SYYS, (where O - diphenyloxide, S - diphenylsulfide, Y - phthalide group). A fundamental difference was established in the chromatographic behavior of diaryl(arylene)diphthalides, built on the principle of "head-to-tail", and diaryldiphthalides with a structure of "head-to-head". The meso and chiral diastereoisomers of the former were eluted by one peak, while the latter existed in solution in the forms of stable cis (racemic form) and trans (meso form) rotamers with different retention times. It was shown that to calculate the retention times of related diarylphthalides, diaryl(arylene)phthalides, diastereoisomeric and enantiomeric diaryldiphthalides of an asymmetric structure, the half-sum rule can be applied according to which: tR(A-X-B)≈[(tR(A-X-A)+tR(B-X-B)]/2. For diaryl(arylene)diphthalides of a triadic structure, a modified additive scheme for calculating retention times is proposed, including multiplication and division operations: tR(A-A-A) = tR(A-A-B) × tR(A-B-B)/tR(B-B-B).
