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dc.contributor.author
Boeselt, Lennard
dc.contributor.author
Doetzer, Reinhard
dc.contributor.author
Steiner, Sandra
dc.contributor.author
Stritzinger, Michaela
dc.contributor.author
Salzmann, Susanne
dc.contributor.author
Riniker, Sereina
dc.date.accessioned
2020-08-01T03:30:16Z
dc.date.available
2020-08-01T03:30:16Z
dc.date.issued
2020-07-07
dc.identifier.other
10.1021/acs.analchem.0c01399
dc.identifier.uri
http://hdl.handle.net/20.500.11850/429551
dc.description.abstract
The relative stereochemistry and isomeric substitution pattern of organic molecules is typically determined using nuclear magnetic resonance spectroscopy (NMR). However, NMR spectra are sometimes nonconclusive, e.g., if spectra are extremely crowded, coupling patterns are not resolved, or if symmetry reasons preclude interpretation. Infrared spectroscopy (IR) can provide additional information in such cases, because IR represents a molecule comprehensively by depiction of the complete set of its normal vibrations. The challenge is thereby that diastereomers and substitution isomers often give rise to highly similar IR spectra, and visual distinction is insufficient and may be biased. Here we show the adaptation of an alignment algorithm, originally developed for vibrational circular dichroism (VCD) spectroscopy, to automatically match IR spectra and provide a quantitative measure of the goodness of fit, which can be used to distinguish isomers. The performance of the approach is demonstrated for different use cases: diastereomers of flexible druglike molecules, E/Z-isomers, and substitution isomers of pyrazine and naphthalene. It can be applied to IR spectra measured both in the gas phase (gas chromatography IR) and in solution.
dc.publisher
AMER CHEMICAL SOC
dc.title
Determining the Regiochemistry and Relative Stereochemistry of Small and Druglike Molecules Using an Alignment Algorithm for Infrared Spectra
dc.type
Journal Article
ethz.journal.title
Analytical chemistry
ethz.journal.volume
92
ethz.journal.issue
13
ethz.journal.abbreviated
Anal. chem. (Wash.)
ethz.pages.start
9124
ethz.pages.end
9131
ethz.identifier.wos
ethz.publication.place
WASHINGTON
ethz.date.deposited
2020-08-01T03:30:26Z
ethz.source
WOS
ethz.rosetta.exportRequired
true
ethz.COinS
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