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- Title
Synthesis and structure of large 24-mer and 36-mer oxamate-based macrocycles.
- Authors
Weheabby, Saddam; Abdulmalic, Mohammad A.; Kataev, Evgeny A.; Shumilova, Tatiana A.; Rüffer, Tobias
- Abstract
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 [NH4][CO2H] and Pd/C, N,N'-bis(2-aminophenyl)oxalamide (2, bapoxH6) 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 H8L² was obtained. In analogues experiments, the addition of ethoxalyl and oxalyl chloride to 2 afforded the 36-membered macrocycle H12L³. The addition of Cu(OAc)2· H2O and NaOH to 2 gave rise to the formation of [Cu2(bapoxH4) (OAc)2](4). The identities of 1, 2 and H8L² were determined by elemental analysis, IR, NMR spectroscopic studies and by mass spectrometry. The solid state structures of H8L², H12L³ and 4 have been determined by single-crystal X-ray diffraction studies. Macrocycle H12L³ forms chains through intermolecular hydrogen bonds, while packing of 4 consists of layers held by intermolecular dispersion and hydrogen bond interactions. 24-mer H8L² forms a cavity with a diameter of about 7.5 Å corresponding to an accessible volume of about 120 Å3 according to the well-established 55% solution and was found to bind bromide and iodide anions selectively.
- Subjects
MACROCYCLIC compound synthesis; POLYCYCLIC compounds; NITROANILINE; OXALYL chloride; NUCLEAR magnetic resonance spectroscopy; X-ray diffraction
- Publication
Zeitschrift für Naturforschung B: A Journal of Chemical Sciences, 2017, Vol 72, Issue 7, p461
- ISSN
0932-0776
- Publication type
Article
- DOI
10.1515/znb-2017-0020