Impact of Solvent and Protonation State on Rotational Barriers in [s]-Triazines.

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-d₆, MeCN-d₃, MeOD-d₄, tetrahydrofuran-d₈, trifluoroethanol-d₃). Furthermore, ΔG^‡ increases as the solvent dielectric decreases (p < 0.01). This trend is consistent with the role that solvent plays in stabilizing the increased charg

SUBMITTER: Claton LE 

PROVIDER: S-EPMC11830392 | biostudies-literature | 2024 Apr

REPOSITORIES: biostudies-literature