To Avoid Chasing Incorrect Chemical Structures of Chiral Compounds: Raman Optical Activity and Vibrational Circular Dichroism Spectroscopies.

Autor: Polavarapu PL; Department of Chemistry, Vanderbilt University, 7330 Stevenson Center, Nashville, TN, 37235, USA., Covington CL; Department of Chemistry, Vanderbilt University, 7330 Stevenson Center, Nashville, TN, 37235, USA., Raghavan V; Department of Chemistry, Vanderbilt University, 7330 Stevenson Center, Nashville, TN, 37235, USA.
Jazyk: angličtina
Zdroj: Chemphyschem : a European journal of chemical physics and physical chemistry [Chemphyschem] 2017 Sep 20; Vol. 18 (18), pp. 2459-2465. Date of Electronic Publication: 2017 Aug 04.
DOI: 10.1002/cphc.201700764
Abstrakt: 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 misidentified and later corrected, and these errors were often discovered during the total synthesis of natural products. In this work, we present a new and convenient approach that can be used with Raman optical activity (ROA) and vibrational circular dichroism (VCD) spectroscopies, to distinguish between the correct and incorrect CSs of chiral compounds. This approach involves analyzing the spectral similarity overlap between experimental spectra and those predicted with advanced quantum chemical theories. Significant labor needed for establishing the correct CSs via chemical syntheses of chiral natural products can thus be avoided.
(© 2017 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.)
Databáze: MEDLINE
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