biostudies-literatureKim JNational Research Foundation of Korea163https://www.ebi.ac.uk/biostudies/studies/S-EPMC9820443biostudies-literatureUnknown24(1)A naphthalene imide (<b>1</b>) and a naphthalene (<b>2</b>) 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 <b>1</b> and <b>2</b> bind various anions via hydrogen bonds using both C-H and N-H donors. Compared with receptor <b>2</b>, receptor <b>1</b> 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 International journal of molecular sciencesMolecular Pincers Using a Combination of N-H and C-H Donors for Anion Binding.PMC98204432021R1A2C1012140Kim SHHeo NJHay BPKim JKim SKfalseMolecular Pincers Using a Combination of N-H and C-H Donors for Anion Binding.A naphthalene imide (<b>1</b>) and a naphthalene (<b>2</b>) 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 <b>1</b> and <b>2</b> bind various anions via hydrogen bonds using both C-H and N-H donors. Compared with receptor <b>2</b>, receptor <b>1</b> 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 2022-01-01T00:00:00Z2022 Dec2025-04-04T20:32:55.534Z2024-11-08T22:07:06.933ZS-EPMC98204433661360810.3390/ijms24010163