New multifunctional phosphonic acid for metal phosphonate synthesis

A new heterotopic phosphonic acid, 3-amino-5-(dihydroxyphosphoryl)benzoic acid (1) has been synthesized and obtained in the crystalline form. Second multifunctional phosphonic acid – namely 3-(dihydroxyphosphoryl)-5-nitrobenzoic acid (2) has also been obtained, following a different synthetic route than previously reported. Compound 1 crystallizes in a centrosymmetric space group of the triclinic system as monohydrate, C6H3(NH2)(COOH)PO3H2·H2O – 1a. The molecule in the crystal exists in a zwitterionic form, in which one of the proton of the phosphonic group is transferred to the amine group. The zwitterionic molecules interact to each other and with water molecules via NH…O and OH…O hydrogen bonds forming a three-dimensional network.

► A new multifunctional phosphonic acid, 3-amino-5-(dihydroxyphosphoryl)benzoic acid, has been synthesized and characterized. ► It crystallizes in P−1 space group and forms a three dimensional supramolecular structure using seven hydrogen bonds. ► Molecular structure makes it potentially interesting for synthesis of open framework metal phosphonates.