Molecular Pincers Using a Combination of N-H and C-H Donors for Anion Binding.

ABSTRACT: A naphthalene imide (1) and a naphthalene (2) bearing two pyrrole units have been synthesized, respectively, as anion receptors. It was revealed by ¹H NMR spectral studies carried out in CD₃CN that receptors 1 and 2 bind various anions via hydrogen bonds using both C-H and N-H donors. Compared with receptor 2, receptor 1 shows higher affinity for the test anions because of the enhanced acidity of its pyrrole NH and naphthalene CH hydrogens by the electron-withdrawing imide substituent. Molecular mechanics computations demonstrate that the receptors contact the halide anions via only one of the two respective available N-H and C-H donors whereas they use all four donors for binding of the oxyanions such as dihydrogen phosphate

SUBMITTER: Kim J 

PROVIDER: S-EPMC9820443 | biostudies-literature | 2022 Dec

REPOSITORIES: biostudies-literature