How does excited-state antiaromaticity affect the acidity strengths of photoacids?
Zhili Wen, Lucas J. Karas, Chia‐Hua Wu, Judy I. Wu
Abstract
Photoacids like substituted naphthalenes (X = OH, NH3+, COOH) are aromatic in the S0 state and antiaromatic in the S1 state. Nucleus independent chemical shifts analyses reveal that deprotonation relieves antiaromaticity in the excited conjugate base, and that the degree of "antiaromaticity relief" explains why some photoacids are stronger than others.
Topics & Concepts
AntiaromaticityExcited stateChemistryPhotochemistryState (computer science)Chemical physicsComputational chemistryAromaticityOrganic chemistryAtomic physicsMoleculePhysicsAlgorithmComputer sciencePhotochromic and Fluorescence ChemistryPhotochemistry and Electron Transfer StudiesRadical Photochemical Reactions