Benchtop NMR Spectroscopy and Spectral Analysis of the cis- and trans-Stilbene Products of the Wittig Reaction

Abstract

Benchtop NMR spectrometers are now becoming more widely employed in university teaching laboratories. These low-field instruments are increasingly used in reaction monitoring and product purity applications. NMR spectra obtained using these spectrometers (40–80 MHz) tend to suffer from significant overlap of signals when compared to those obtained at 300–400 MHz or above, and therefore, some reactions may be less suited to analysis using such benchtop systems. While some reactions can be modified to make them more amenable to analysis on low-field benchtop spectrometers, the fact remains that many common undergraduate laboratory chemistry reactions remain as a stalwart of the university education system. Therefore, there is currently a major requirement for benchtop NMR analysis to improve in order to facilitate student understanding. Herein, it is demonstrated that a combination of spectral analysis and simulation at low-fields (40–80 MHz) allows the fine structure of second-order effects and overlapping spectra to be deduced, enabling an improved understanding of the low-field benchtop NMR technique within undergraduate student cohorts. The evolution of well-resolved and distinct multiplets at 400 MHz to complex, overlapping multiplets at 40–80 MHz also serves as a useful guide for laboratory demonstrators and academic staff when explaining the advantages of such benchtop systems. The Wittig reaction has been a standard reaction practical session in many university teaching laboratories since the 1980s, the products of which are a mixture of cis- and trans-stilbenes. This reaction serves as an ideal example of how benchtop NMR spectrometers and analysis can support chemistry teaching laboratories.

Description

The file attached to this record is the author's final peer reviewed version. The Publisher's final version can be found by following the DOI link.

Keywords

Citation

Edgar, M., Percival, B.C., Gibson, M., Masania, J., Beresford, K., Wilson, P.B. and Grootveld, M., (2019) Benchtop NMR Spectroscopy and Spectral Analysis of the cis-and trans-Stilbene Products of the Wittig Reaction. Journal of Chemical Education. 96 (9), pp. 1938-1947

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Research Institute

Leicester Institute for Pharmaceutical Innovation - From Molecules to Practice (LIPI)