NMR spectroscopy and computational tools that assist with interpretation and analysis have been implemented into the organic chemistry sequence at SUNY Oneonta. In the sophomore organic chemistry course, NMR spectroscopy (proton, carbon-13, and DEPT-135) is introduced early in the first semester as part of a multi-week laboratory project that combines unknown identification with a green synthesis. Students use NMR, along with IR spectroscopy and physical data, to identify two unknowns that are later reacted together to form imines via a green synthetic method. Every student in the course receives a unique combination of unknowns and, thus, synthesizes a unique imine. Students work through the unknown identification process over three weeks: Week 1–IR to identify functional groups; Week 2–carbon-13 and DEPT-135 NMR to propose reasonable structures; and Week 3–proton NMR to propose the final, exact structures. During Week 2, students use ChemDoodle to predict carbon-13 spectra for candidate structures and compare these spectra with their experimental spectra. During Week 3, students look up literature spectra of their proposed final structures, usually on Spectral Database for Organic Compounds (SDBS), and compare them to their experimental spectra for confirmation. In subsequent weeks, the reaction is performed and students analyze their imine products by NMR. A library of imine spectra resulting from this project has been deposited to the Royal Society of Chemistry's ChemSpider database, as most of these spectra are not available in other databases. One benefit to ChemSpider is that spectra deposited there are interactive, so one can zoom in on regions of unclear splitting. Students learn to process raw data using JEOL's Delta software, which is used routinely throughout the full-year organic course. Spectra with complex splitting are interpreted with the aid of ChemDoodle's NMR SignalSeek and Multiplet Tool widgets. In addition, the imine product is evaluated for percent purity using quantitative NMR (qNMR). This talk will provide an overview to how computational tools assist in teaching NMR concepts, the pros and cons of the various computational packages used, and the potential pedagogical uses for the NMR data deposited on ChemSpider.

NMR spectroscopy and complementary computational tools: Delta for 1D processing, ChemDoodle for predictions, and ChemSpider for interactive literature spectra

253rd National Meeting (2017)

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