The relative rates of iron pentacarbonyl-catalyzed photo-induced isomerization of allyl alcohol in various solvents have been studied using 1H NMR spectroscopy. The reactions were run in linear and cyclic alkanes, alcohols, and amines in order to investigate whether the presence of these solvents would affect the production of propanal upon UV irradiation of the reaction mixture. The rates of isomerization were efficient in nonane, hexane, cyclohexane, and benzene. The reaction rates were very slow or completely suppressed in ethanol, propanol, isopropyl alcohol, triethylamine, and pyridine. Density functional theory (DFT) was employed to calculate the thermodynamics of the interaction between the solvents of this study and the transient iron carbonyl species in order to rationalize the rate data. The suppression of the isomerization was attributed to strong interactions between the unsaturated iron carbonyl intermediates and a solvent molecule.

Combined <sup>1</sup>H NMR and DFT study of the solvent effects on the iron pentacarbonyl-catalyzed photo-assisted isomerization of allyl alcohol

245th National Meeting (2013)

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Combined 1H NMR and DFT study of the solvent effects on the iron pentacarbonyl-catalyzed photo-assisted isomerization of allyl alcohol

Combined ¹H NMR and DFT study of the solvent effects on the iron pentacarbonyl-catalyzed photo-assisted isomerization of allyl alcohol