Synthesis, Spectroscopy, and Stability of the Nitric Oxide Donor S -nitroso- N -acetylpenicillamine: An Undergraduate Laboratory Experiment
Year: 2017
Type: article
Abstract: In the following experiment, organic chemistry students will gain hands-on experience with ultraviolet-visible and 1HNMR spectroscopy after synthesizing S-nitroso-N-acetyl-D-penicillamine (SNAP). SNAP is a popular small molecule nitric oxide (NO) donor that has shown promise for biomedical applications. Our group has consistently demonstrated that polymers, such as silicone rubber or polyurethanes, containing SNAP can release NO and use its potent antithrombotic and antimicrobial properties to prevent clot and bacteria biofilm formation. Following the straightforward acid catalyzed synthesis, students will characterize the product with 1HNMR. Studying SNAP’s 1HNMR spectrum exposes students to a variety of crucial concepts, including chemical shifts, integration, topicity, multiplicity, and coupling constants. Students can also calculate SNAP’s molar absorptivity using UV-Vis spectroscopy, and use it to monitor the compound’s stability in various environments. The experiment is presented in a manner most appropriate for an undergraduate, second-semester organic laboratory course; however, it can be readily tailored to first-semester students by omitting the 1HNMR portion. The stability tests are suitable for various environments and durations, allowing the experiment to be used for single or multiple class periods as desired.
Language: English
Subfield: Education
Field: Social Sciences
Domain: Social Sciences
Open Access status: diamond
OpenAlex ID: W2741186965