Protic vs Aprotic Solvent Effect on Proton Transfer in 3-Hydroxyisoquinoline: A Theoretical Study.

ABSTRACT

In this work, the structures, energetics, and tautomerizations in 3-hydroxyisoquinoline (3HIQ) in both the ground state and the excited state have been theoretically investigated by the MP2, TDDFT, and CASPT2 methods, respectively. The solvent effect including the implicit solvent and explicit solvent on the structures, energetics, and tautomeizations are revealed. We found that the explicit solvent plays a more important role in the structures, energetics, and tautomerizations in 3HIQ than implicit solvent in both the ground state and the excited state. The proton transfer is more facilitated in explicit solvent (water or methanol) compared to that in the gas phase and in the implicit solvent in the excited state, and the reactive role of the molecular solvent is found to be related with the two linear hydrogen bonds.