Based on the pseudo-antiaromatic electronic structure provided in Scheme 2, we hypothesize that a positive charge will form on the O carbonyl, ultimately preventing H-bonding on the excited state. While stabilizing on the ground state when oxygen has two electron lone pairs, this interaction becomes repulsive after the n O → π * CC is excited to the S 1 . To test this hypothesis, we quantified the degree of H-bonding in the productive and non-productive trajectory pathways to determine how this electronic structure affected the intermolecular H-bonding interactions. After analyzing the full trajectory pathways of 1, we computed that 22% of productive trajectories have hydrogen bonding, while 34% of non-productive trajectories have hydrogen bonding. For the trajectory pathways of 2, we computed that 17% of productive trajectories have hydrogen bonding, while 43% of non-productive trajectories have hydrogen bonding. The productive trajectories overwhelmingly access the asynchronous hopping point geometries, which feature a broken σ CC bond in the cyclopropenone ring. The lack of hydrogen bonding throughout the productive trajectories suggests that it is not stabilizing for the O carbonyl to be interacting with the surrounding water molecules. The non-productive trajectories have much higher levels of Hbonding, which is consistent with the S 0 pseudo-aromatic electronic structure where the cyclopropenone ring is still fully formed, and the O carbonyl possesses two lone pairs to participate in intermolecular H-bonding.