Aromatic imine compounds have shown significant potential not only in their importance as intermediaries in organic synthesis, but in their own ability to bind with metal cations, sometimes selectively. Previous work has correlated the NMR shift of the N=CH proton on aryl aldimines with the combined Hammett parameters of the substituents on the aldehyde and aniline materials used to form the aryl aldimine. This project looks to determine the difference in effect of aldehyde versus aniline substituents on the NMR shift of the N=CH proton. Using <sup>1</sup>H and <sup>15</sup>N NMR spectroscopy, the change in NMR shift of the N=CH proton between the imine and iminium forms of the aryl aldimine were monitored. Given not only the importance of imine compounds as precursors to important organic products, but also their own importance as metal-binding ligands, a better understanding of electronic effects on aryl aldimines can help guide the development of aryl aldimines with stronger and/or more specific metal binding sites.

Substituent effect on aromatic imine basicity

2019 Spring National Meeting

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