A chemical structure (CS) identifies the connectivities between atoms, and the nature of those connections, for a given elemental composition. For chiral molecules, in addition to the identification of CS, the identification of the correct absolute configuration (AC) is also needed. Several chiral natural products are known whose CSs were initially mis-identified and later corrected, and these errors were often discovered during the total synthesis or retrosynthesis of natural products. Can chiroptical spectroscopy help identify the mis-identified chiral chemical structures ? To answer this question, chiroptical spectra have been calculated for previously mis-identified chiral chemical structures of eight compounds and analyzed with those for corresponding correct chiral chemical structures, using CDSpecTech software developed in our laboratory for similarity overlap analysis. This analysis indicates that vibrational Raman optical activity and vibrational circular dichroism spectra, when investigated together, have the potential to identify the mis-identified chiral chemical structures.

The use of chiroptical spectroscopy for identifying mis-identified chiral chemical structures

255th National Meeting (2018)

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