Files in this item

FilesDescriptionFormat

application/vnd.openxmlformats-officedocument.presentationml.presentation

application/vnd.openxmlformats-officedocument.presentationml.presentation1413684.pptx (2MB)
PresentationMicrosoft PowerPoint 2007

application/pdf

application/pdf3852.pdf (15kB)
AbstractPDF

Description

Title:THE CONVERSION OF STYRENE OXIDE ENANTIOMERS INTO SPECTROSCOPICALLY DISTINGUISHABLE DIASTEREOMERS THROUGH COMPLEXATION WITH 3,3,3-TRIFLUORO-1,2-EPOXYPROPANE
Author(s):Marshall, Mark D.
Contributor(s):Krin, Anna ; Domingos, Sergio R; Schnell, Melanie ; Leung, Helen O.
Subject(s):Mini-symposium: Non-covalent Interactions
Abstract:3,3,3-Trifluoro-1,2-epoxypropane [2-(trifluoromethyl)-oxirane, or TFO] has shown promise as a tag for chiral analysis through conversion of enantiomers into spectroscopically distinguishable diastereomers via the formation of non-covalently bound heterodimers. We demonstrate the suitability of this method through characterization of the microwave rotational spectrum of complexes formed between TFO and styrene oxide (SO). Molecular dynamics calculations are used to quickly identify possible heterodimer conformations which are then optimized and evaluated using density functional theory. Using a mixture of racemic samples of both species, we observe and assign spectra for the lowest energy conformers of both homochiral (RR/SS)-TFO-SO and heterochiral (RS/SR)-TFO-SO. Had a single enantiomer of TFO been used, say (R), the spectra are sufficiently distinct and sufficiently well predicted by theory that (RR)-TFO-SO and (RS)-TFO-SO are readily identified and separately analyzed.
Issue Date:2019-06-20
Publisher:International Symposium on Molecular Spectroscopy
Genre:Conference Paper / Presentation
Type:Text
Language:English
URI:http://hdl.handle.net/2142/104306
DOI:10.15278/isms.2019.RH02
Rights Information:Copyright 2019 Mark D. Marshall
Date Available in IDEALS:2019-07-15
2020-01-25


This item appears in the following Collection(s)

Item Statistics