Hydrogen bonding in phthalimido carboxylic acids: cyclic voltammetric study and correlation with photochemical reactivity, part 2, aliphatic and aromatic acids

Cyclic voltammetry was applied as a useful tool for the detection and semiquantitative assessment of hydrogen bonding in phthalimidoalkyl and aryl carboxylic acids in solution. Both intra- and intermolecular hydrogen bonding could be detected and were assigned on the basis of base (DBU), acid (trifluoromethanesulfonic acid), solvent (MeCN vs. DMF), concentration and scan rate effects, as well as multisweep experiments. The observation of intramolecular hydrogen bonding neatly correlates with the reactivity pattern of the corresponding phthalimido carboxylic acids in photodecarboxylation reactions

Structural, CV and IR spectroscopic evidences for preorientation in PET-active phthalimido carboxylic\ud acids

Hydrogen bond and potassium cation mediated preorientation were detected for phthalimido acetic acid and the corresponding acetate. Evidence for these phenomena came from X-ray structure analysis as well as cyclic voltammetric and IR spectroscopic measurements. These interactions rationalize the photoinduced electron transfer (PET) reactivity of the substrates in photodecarboxylation reactions