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Poly(cyclic) oxamates represent novel and potentially multidentate ligands for coordination chemistry. To obtain them, the treatment of 2-nitroaniline with two equivalents of oxalyl chloride afforded  N,N ′-bis(2-nitrophenyl)oxalamide ( 1 ), and by reduction of  1  with [NH 4 ][CO 2 H] and Pd/C,  N,N ′-bis(2-aminophenyl)oxalamide ( 2 , bapoxH 6 ) was synthesized. After the addition of an equimolar amount of oxalyl chloride to a THF solution of  2  and aqueous work-up the 24-membered macrocycle H 8 L 2  was obtained. In analogues experiments, the addition of ethoxalyl and oxalyl chloride to  2  afforded the 36-membered macrocycle H 12 L 3 . The addition of Cu(OAc) 2 ·H 2 O and NaOH to  2  gave rise to the formation of [Cu 2 (bapoxH 4 )(OAc) 2 ] ( 4 ). The identities of  1 ,  2  and H 8 L 2  were determined by elemental analysis, IR, NMR spectroscopic studies and by mass spectrometry. The solid state structures of H 8 L 2 , H 12 L 3  and  4  have been determined by single-crystal X-ray diffraction studies. Macrocycle H 12 L 3  forms chains through intermolecular hydrogen bonds, while packing of  4  consists of layers held by intermolecular dispersion and hydrogen bond interactions. 24-mer H 8 L 2  forms a cavity with a diameter of about 7.5 Å corresponding to an accessible volume of about 120 Å 3  according to the well-established 55% solution and was found to bind bromide and iodide anions selectively.

Synthesis and structure of large 24-mer and 36-mer oxamate-based macrocycles