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A Versatile New Reagent for Nitrosation under Mild Conditions

preprint
submitted on 07.02.2021, 06:00 and posted on 08.02.2021, 12:16 by Jordan D. Galloway, Cristian Sarabia, James C. Fettinger, Hrant Hratchian, Ryan Baxter
We report a new chemical reagent for transnitrosation under mild experimental conditions. This new reagent is stable to air and moisture across a broad range of temperatures, and is effective for transnitrosation in multiple solvents. Compared to traditional nitrosation methods, our reagent shows high functional group tolerance for substrates that are susceptible to oxidation or reversible transnitrosation. Several challenging nitroso-compounds are accessed here for the first time, including 15N isotopologues. X-ray data confirms two rotational isomers of the reagent are configurationally stable at room temperature, although only one isomer is effective for transnitrosation. Computational analysis describes the energetics of rotamer interconversion, including interesting geometry-dependent hybridization ef-fects.

Funding

1752812

MRI: Acquisition of Pinnacles -- Raising Research Computing to New Heights in California's Central Valley

Directorate for Computer & Information Science & Engineering

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MRI Acquisition: Multi-Environment Research Computer for Exploration and Discovery (MERCED) Cluster

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History

Email Address of Submitting Author

rbaxter@ucmerced.edu

Institution

University of California, Merced

Country

United States

ORCID For Submitting Author

0000-0002-1341-5315

Declaration of Conflict of Interest

None

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ChemRxiv

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