Jensen, Katrina

• Ph.D., Organic Chemistry, University of Utah, Salt Lake City 

• B.S., Chemistry, Black Hills State University, Spearfish

Nuclear Magnetic Resonance (NMR) spectroscopy is a vital tool used by chemists to determine the structure of organic molecules. This technology is essential for organic synthesis, medicinal chemistry, and drug design. Because NMR analysis is central to organic structure characterization, the subject is standard in organic chemistry courses and is tested on exams such as the MCAT and DAT. The goal of this research is to develop an educational game that will motivate students to learn this topic. 

The challenge of NMR interpretation is viewing the information provided by the peaks of an NMR spectrum (Fig. 1, left), and translating that data into the molecular structure, i.e. the number and type of atoms in a molecule, and how those atoms are connected to each other (Fig. 1, right). We aim to develop a game that provides spectra to solve as puzzles, encouraging students to learn NMR interpretation. During game play, students will solve puzzles using the data in an NMR (including the number, shape, location, and area of peaks) to discover the number of hydrogen atoms in the molecule, how these atoms are grouped, whether one atom is adjacent to another, and what bonding patterns are present.

One challenge of game development is maintaining player motivation, which we aim to do in part by introducing puzzles that are suitably challenging, but don't get difficult too quickly.  A goal of this project will be to develop a ranking system to quantify the complexity of NMR spectra, so that when a player in the game encounters a new problem, they are given puzzles that are appropriate for their skill level. We will evaluate factors that give rise to spectral complexity and develop a system to quantify complexity that will guide at which level a player in the game should encounter a particular puzzle. 

In order to include a broad variety of difficulty in the game, we are working to develop a database of NMR spectra by synthesizing a library of organic molecules and collecting their NMR spectra. Molecules targeted for synthesis will be designed to have a variety of molecular and predicted spectral complexity, while being easily synthesized from readily available reagents. For example, an extensive library of compounds could be synthesized starting from hydroxy benzoic acids matched with different alcohol or alkyl halide reagents used to derivatize the ester and phenolic ether functional groups, respectively (Fig. 2). The library of compounds (and thus the database of spectra) could grow exponentially with each variation in the R1 and R2 groups. As the library is expanded, compounds will be targeted to include diverse structures and functional groups to provide a database of NMR spectra that spans a spectrum of complexity that would provide challenging puzzles for players of the game that range from students just beginning organic chemistry to graduate students learning advanced spectral analysis.

Students working on this project will synthesize compounds and collect and analyze spectra to be included in the game, as well as participate in game design and evaluation of its efficacy. Students will gain skills in advanced organic chemistry, including reaction design and setup, product purification and characterization, and NMR spectral collection and analysis. Students will also practice skills that are broadly applicable, including experimental design, problem solving, data management, safety, and science communication. The long-term goals of this project are to create an open-access game that is freely available to play, incudes the gradient of difficulty so that beginners and more advanced students can use the game, and allows other researchers to contribute spectra to be included in the game.