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PubMed · 11552802

Determining absolute configuration in flexible molecules: a case study.

K M Specht·J Nam·D M Ho·N Berova·R K Kondru·D N Beratan·P Wipf·R A Pascal·D Kahne
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Abstract

Assigning absolute configuration of molecules continues to be a major problem. Determining absolute configuration in conformationally flexible systems is challenging, even for experts. Here, we present a case study in which we use a combination of molecular modeling, solution NMR, and X-ray crystallography to illustrate why it is difficult to use solution methods alone for configuration assignment. For the case examined, a comparison of calculated and experimental optical rotatory dispersion (ORD) data provides the most straightforward way to assign the absolute configuration.

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BenzoatesCircular DichroismCrystallography, X-RayMolecular ConformationNaphthalenesOptical Rotatory DispersionSolutionsStereoisomerismThermodynamicsJournal ArticleResearch Support, Non-U.S. Gov'tResearch Support, U.S. Gov't, Non-P.H.S.Research Support, U.S. Gov't, P.H.S.

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K M Specht, J Nam, D M Ho, N Berova, R K Kondru, D N Beratan, P Wipf, R A Pascal, D Kahne. 2001-09-19. Determining absolute configuration in flexible molecules: a case study.. https://doi.org/10.1021/ja0104406

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