2024
DOI: 10.1021/acs.joc.3c02918
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Impact of Solvent and Protonation State on Rotational Barriers in [s]-Triazines

Liam E. Claton,
Hongjun Pan,
Eric E. Simanek

Abstract: Amine-substituted [s]-triazines display hindered rotation around the triazine-N bond. While this barrier, ΔG ‡, has been measured to be between 15.1 and 17.7 kcal/mol for neutral triazines, the impacts that solvent and protonation state have not been addressed. Using a dimethylamine substituent as a reporter, ΔG ‡ was measured to be 17.5–19.3 kcal/mol upon protonation across a range of solvents (D2O, DMSO-d 6, MeCN-d 3, MeOD-d 4, tetrahydrofuran-d 8, trifluoroethanol-d 3). Furthermore, ΔG ‡ increases as the so… Show more

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