Interplay of hydrogen bonding in deciding the conformers of psilocin: Computational insights
Abstract
Conformational analysis of psilocin, a psychedelic molecule revealed two stable conformers designated as conformer-A and B which were 4.97 kcal/mol apart in energy among many other high energy conformers. AIM analysis revealed that the conformer-A (global minimum) is stable due to intramolecular H-bond formation between ethyl amine nitrogen and indolic hydroxyl group. This is in contradiction to earlier X-ray crystal studies of this molecule reported in literature. Dimers of both conformer-A and B were studied utilizing DFT method and it was observed that even in the dimer of conformer-A the intramolecular H-bond energy dominates over the intermolecular H-bond. Other calculations namely NBO, FMO, charge analysis, ESP mapping corroborated the AIM results in a significant manner. The spectroscopic study including UV, 1H-NMR and vibrational modes calculation were found to be in good agreement with the data reported in literature.
Topics & conditions
Detected automatically by Psychedelic Commons from the title and abstract, not labels from the source. They may be incomplete.
Psychedelic Commons aggregates metadata from open sources and links back to the original. Rights remain with the authors and publishers. Something wrong with this record? Report a problem.