Additivity of retention of diastereoisomeric and enantiomeric arylphthalides, aryl(arylene)phthalides and aryldiphthalides of dyadic and triadic composition

V A Kraikin; N G Gileva; T A Yangirov; S P Ivanov; A A Fatykhov; V A Davankov; M M Ilyin; S N Salazkin

doi:10.1016/j.chroma.2020.461527

Additivity of retention of diastereoisomeric and enantiomeric arylphthalides, aryl(arylene)phthalides and aryldiphthalides of dyadic and triadic composition

J Chromatogr A. 2020 Sep 8:1630:461527. doi: 10.1016/j.chroma.2020.461527. Online ahead of print.

Authors

V A Kraikin¹, N G Gileva², T A Yangirov², S P Ivanov², A A Fatykhov², V A Davankov³, M M Ilyin³, S N Salazkin³

Affiliations

¹ Ufa Institute of Chemistry of the Ufa Federal Research Centre, Russian Academy of Sciences, Prospekt Oktyabrya 69, Ufa 450054, Russia. Electronic address: kraikin@anrb.ru.
² Ufa Institute of Chemistry of the Ufa Federal Research Centre, Russian Academy of Sciences, Prospekt Oktyabrya 69, Ufa 450054, Russia.
³ A.N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Ul. Vavilova 28, Moscow 119991, Russia.

PMID: 32956856
DOI: 10.1016/j.chroma.2020.461527

Abstract

For the first time, four series of new phthalide-containing heteroaromatic compounds were separated by reverse phase HPLC: O_YO, O_YS, S_YS; O_YO_YO, O_YO_YS, S_YO_YS; S_YS_YS, S_YS_YO, O_YS_YO; O_YYO, O_YYS, S_YYS, (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: t_R(A-X-B)≈[(t_R(A-X-A)+t_R(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: t_R(A-A-A) = t_R(A-A-B) × t_R(A-B-B)/t_R(B-B-B).

Keywords: Aryldiphthalides; Arylphthalides; Half-sum rule; Retention additivity; Retention time.