Synthesis, complexation and cyclisation reactions of a new acyclic diamide: observation of intramolecular ligand exchange in a structurally characterised nickel(II) complex
A new acyclic diamide ligand H 2L1 has been prepared and characterised H 2L12 6-bis(1-propanecarboxamido-3-amino)pyridine is prepared from 26-dimethylpyridinedicarboxylate and excess 13-diaminopropane Nickel(II) complexes derived from H 2L1 [Ni(L1+H)]X are orange square planar and diamagnetic (X=ClO...
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| Published in: | Polyhedron Vol. 18; no. 5; pp. 679 - 688 |
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| Main Authors: | , , |
| Format: | Journal Article |
| Language: | English |
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Elsevier Ltd
01-01-1999
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| Abstract | A new acyclic diamide ligand H
2L1 has been prepared and characterised H
2L12 6-bis(1-propanecarboxamido-3-amino)pyridine is prepared from 26-dimethylpyridinedicarboxylate and excess 13-diaminopropane Nickel(II) complexes derived from H
2L1 [Ni(L1+H)]X are orange square planar and diamagnetic (X=ClO
4
− CF
3SO
3
− or NO
3
−) A single-crystal X-ray analysis of [Ni(L1+H)]ClO
4 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 H
2L1 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(H
2L2)](ClO
4)
2 and [Ba (H
2L3)] (ClO
4)
2 respectively In contrast to the template cyclisations a symmetrical metal-free tetraamide macrocycle H
4L4 is produced from the direct cyclisation of H
2L1 with 2 6-dimethylpyridinedicarboxylate. |
|---|---|
| AbstractList | A new acyclic diamide ligand H
2L1 has been prepared and characterised H
2L12 6-bis(1-propanecarboxamido-3-amino)pyridine is prepared from 26-dimethylpyridinedicarboxylate and excess 13-diaminopropane Nickel(II) complexes derived from H
2L1 [Ni(L1+H)]X are orange square planar and diamagnetic (X=ClO
4
− CF
3SO
3
− or NO
3
−) A single-crystal X-ray analysis of [Ni(L1+H)]ClO
4 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 H
2L1 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(H
2L2)](ClO
4)
2 and [Ba (H
2L3)] (ClO
4)
2 respectively In contrast to the template cyclisations a symmetrical metal-free tetraamide macrocycle H
4L4 is produced from the direct cyclisation of H
2L1 with 2 6-dimethylpyridinedicarboxylate. |
| Author | Jameson, Geoffrey B Brooker, Sally Dunbar, Geoffrey S |
| Author_xml | – sequence: 1 givenname: Sally surname: Brooker fullname: Brooker, Sally organization: Department of Chemistry, University of Otago, P.O. Box 56, Dunedin, New Zealand – sequence: 2 givenname: Geoffrey S surname: Dunbar fullname: Dunbar, Geoffrey S organization: Department of Chemistry, University of Otago, P.O. Box 56, Dunedin, New Zealand – sequence: 3 givenname: Geoffrey B surname: Jameson fullname: Jameson, Geoffrey B organization: Institute of Fundamental Sciences, Chemistry, Massey University, P.O. Box 11222, Palmerston North, New Zealand |
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| CitedBy_id | crossref_primary_10_1007_s10870_007_9302_x crossref_primary_10_1081_SIM_200055675 crossref_primary_10_1016_j_saa_2008_12_019 crossref_primary_10_1080_10610278_2017_1358449 crossref_primary_10_1016_S0020_1693_00_00089_X crossref_primary_10_1002_cjoc_200590437 crossref_primary_10_1016_j_ccr_2012_03_024 crossref_primary_10_1016_S0020_1693_02_00871_X crossref_primary_10_3987_COM_01_S_K_48 crossref_primary_10_1016_j_molcata_2004_01_019 crossref_primary_10_1016_j_saa_2008_10_053 crossref_primary_10_1016_j_poly_2010_10_012 crossref_primary_10_1016_S0277_5387_00_00506_4 crossref_primary_10_1039_b707905b crossref_primary_10_1155_2014_863612 crossref_primary_10_1039_B308263F crossref_primary_10_1080_01932690802701713 |
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| Keywords | Exchange Amide Barium Nickel Structure |
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| Snippet | A new acyclic diamide ligand H
2L1 has been prepared and characterised H
2L12 6-bis(1-propanecarboxamido-3-amino)pyridine is prepared from... |
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| SubjectTerms | Amide Barium Exchange Nickel Structure |
| Title | 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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