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Synthesis, resolution and crystal structures of two enanti-omeric rhodamine derivatives.

ABSTRACT: The title mol-ecule, rac-6'-bromo-3'-di-ethyl-amino-3H-spiro-[2-benzo-furan-1,9'-xanthen]-3-one, C₂₄H₂₀BrNO₃, was synthesized and the two enanti-omers which formed were separated. The structures of all three compounds were determined and compared with those of a variety of related derivatives. A notable feature is the fold of the xanthene portion which ranges from 15.15?(13)° in the racemate to 2.42?(2)° in one mol-ecule of the R enanti-omer with that for the S enanti-omer having an inter-mediate value. The differences are attributed to the number and severity of inter-molecular inter-actions which include C-H?O hydrogen bonds, C-H??(ring) and, in the S enanti-omer, a ?-stacking inter-action between the carbonyl group and an aromatic ring.

SUBMITTER: Stephenson CJ

PROVIDER: S-EPMC5347046 | biostudies-literature | 2017 Mar

REPOSITORIES: biostudies-literature

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Synthesis, resolution and crystal structures of two enanti-omeric rhodamine derivatives.

Stephenson Clifton J CJ Mague Joel T JT Kamm Nathaniel N Aleman Nathalie N Rich Dayla D Dang Quynh-Nhu QN Nguyen Ha Van HV

Acta crystallographica. Section E, Crystallographic communications 20170203 Pt 3

The title mol-ecule, rac-6'-bromo-3'-di-ethyl-amino-3H-spiro-[2-benzo-furan-1,9'-xanthen]-3-one, C24H20BrNO3, was synthesized and the two enanti-omers which formed were separated. The structures of all three compounds were determined and compared with those of a variety of related derivatives. A notable feature is the fold of the xanthene portion which ranges from 15.15 (13)° in the racemate to 2.42 (2)° in one mol-ecule of the R enanti-omer ...[more]

PMID: 28316801

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