Publication Details
Abstract
The research investigates tautomers of polyfluoroacyl cycloalkanone structures while exploring how fluorine groups and cyclic ring systems affect their enol and diketone tautomerism. The research field of linear β-diketones has been thoroughly studied but investigational work on fluorinated cyclic analogs stays poorly understood. The analysis of tautomeric equilibria occurred through ¹H and ¹³C NMR and IR spectroscopy techniques which evaluated solvents such as CDCl₃, CCl₄, DMFA-d₇. Computer modeling through MINDO/3, MNDO/H, AM1, RMZ and Sybyl provided structural support. Results show that majority of 2-polyfluoroacyl cycloalkanones exist mainly as enols through strong intramolecular hydrogen bonding but 2-perfluorohexanoylcyclododecanone favors the diketone form because of its macrocyclic effects. IR spectral examinations demonstrated simultaneous existence of tautomers as well as chemical shift data supported electronic modifications from the CF₃ groups. The research discoveries create vital knowledge for understanding fluorinated systems that are utilized in drug design and catalysis applications and material science developments. The investigation of dynamic tautomerism requires more research to be done under physiological conditions while expanding studies to include metal-complexed derivatives and heterocyclic systems.