STUDY OF PROTON TRANSFER BETWEEN CARBON ACIDS AND AMINE BASES USING COMPUTATIONAL METHODS

Abstract

In this work, the proton transfer between carbon acids and amine bases was investigated using computational methods. The effect of substitutions on the interaction between 1-nitro-1-(4-nitrophenyl) alkanes (with R = H , CH 3) and 1-5-7-triazabicyclo[4,4,0]dec-5-ene) (TBD) was investigated. The solvent effects on proton transfer reaction between 1-nitro-1-(4-nitrophenyl) alkanes (in which R = H , CH 3) and TBD have been calculated in acetonitrile and water solvents. The products of proton transfer reactions between C -acids and 7-methyl-1-5-7-triazabicyclo[4,4,0]dec-5-ene (MTBD) were dissociated into free ions, while those of the TBD reaction contained a comparable amount of ions and ion pairs. In addition, the free energy of activation for proton transfer reaction between C -acids with R = H , CH 3 and TBD was calculated. The intermolecular hydrogen bonding formation between 4-nitrophenylnitromethane and TBD was investigated using the Hartree–Fock method, density functional theory (DFT), and atoms in molecules (AIM) theory. The effects of hydrogen bonding on structural parameters of model systems were also studied. The results are in agreement with the results of AIM theory.