Simple NAS click-type chemistry was used to design a physical organic chemistry experiment for second-year college students. NAS reactions were performed on 5,10,15,20-tetrakis(2,3,4,5,6-pentafluorophenyl)porphyrin using three different nucleophiles (S, N, O). Substitution occurs preferentially at the 4-position (para) because it is thermodynamically favored, and the 2- and 6- (ortho) positions are kinetically disfavored because of steric interactions with the porphyrin ring. The activation energy depends heavily on the nucleophile. An open-source software (ImageJ from NIH) was used to quantify relative intensities of spots on a TLC plate obtained from different times and varying temperatures. These data were used to generate Arrhenius plots allowing determination of relative activation energies for three different primary nucleophiles. The experiment was developed by five undergraduates and evaluated by 40 organic chemistry II students and eight students in a physical chemistry laboratory. Students gained a deeper understanding of the relationships between the NAS mechanism, Arrhenius plots, and activation energy.

Quantifying activation energy of nucleophilic aromatic substitution on fluorinated porphyrins

256th National Meeting (2018)

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