Synthesis,complexation and cyclisation reactions of a new acyclic diamide: observation of intramolecular ligand exchange in a structurally characterised nickel(II) complex |
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| Affiliation: | 1. Department of Chemistry, University of Otago, P.O. Box 56, Dunedin, New Zealand;2. Institute of Fundamental Sciences, Chemistry, Massey University, P.O. Box 11222, Palmerston North, New Zealand;1. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, Mashhad 917751436, Iran;2. Department of Chemistry, Hakim Sabzevari University, Sabzevar 96179-76487, Iran;3. Department of Chemistry, Tulane University, New Orleans, LA 70118, USA;1. Wuhan Institute of Technology, Wuhan 430074, China;2. Engineering Research Center of Nano-Geo Materials of Ministry of Education, China University of Geosciences, Wuhan 430074, China;1. Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh, 11451, Saudi Arabia;2. Department of Advanced Materials Chemistry, Dongguk University-Gyeongju, 123 Dongdae-ro, Gyeongju, Gyeongbuk, Republic of Korea;3. Institute of Industry Academy Cooperation Foundation, Dongguk University-Gyeongju, 123 Dongdae-ro, Gyeongju, Gyeongbuk, Republic of Korea;4. Institute of General and Ecological Chemistry, Lodz University of Technology, Zeromskiego 116, 90-924, Lodz, Poland;1. Department of Chemistry and Biochemistry, Duquesne University, 600 Forbes Ave, Pittsburgh, PA, 15282, USA;2. Mass Spectrometry and Proteomics Facility, Campus Chemical Instrument Center, The Ohio State University, Columbus, OH, 43210, USA;3. Department of Physics, Duquesne University, 600 Forbes Ave, Pittsburgh, PA, 15282, USA |
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| Abstract: | A new acyclic diamide ligand H2L1 has been prepared and characterised H2L12 6-bis(1-propanecarboxamido-3-amino)pyridine is prepared from 26-dimethylpyridinedicarboxylate and excess 13-diaminopropane Nickel(II) complexes derived from H2L1 [Ni(L1+H)]X are orange square planar and diamagnetic (X=ClO4− CF3SO3− or NO3−) A single-crystal X-ray analysis of [Ni(L1+H)]ClO4 confirmed that both of the amide groups are deprotonated and are bound to the nickel ion with a trans-amide configuration and that the remaining coordination sites are occupied by the pyridine nitrogen atom and one of the amine arms The second amine arm is protonated and participates in an array of hydrogen bonds in the solid state In solution intramolecular exchange of the arms is observed on the NMR timescale Three macrocycles have been prepared from this acyclic ligand Reaction of H2L1 with 26-diacetylpyridine or 2 6-diformylpyridine in the presence of a barium(II) template ionresults in two new unsymmetrical amide-containing and potentially dinucleating macrocycles as the complexes [Ba(H2L2)](ClO4)2 and [Ba (H2L3)] (ClO4)2 respectively In contrast to the template cyclisations a symmetrical metal-free tetraamide macrocycle H4L4 is produced from the direct cyclisation of H2L1 with 2 6-dimethylpyridinedicarboxylate. |
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