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Structural diversity in the first metal complexes of 2,5-dicarboxamidopyrroles and 2,5-dicarbothioamidopyrroles

Structural diversity in the first metal complexes of 2,5-dicarboxamidopyrroles and 2,5-dicarbothioamidopyrroles
Structural diversity in the first metal complexes of 2,5-dicarboxamidopyrroles and 2,5-dicarbothioamidopyrroles
Metal complexes of 2,5-dicarboxamidopyrroles and 2,5-dicarbothioamidopyrroles have been structurally characterised for the first time, complementing the significant amount of work that has been reported for the analogous pyridine ligands. N,N-Bis(3,5-dinitrophenyl)-3,4-diphenyl-1H-pyrrole-2,5-dicarboxamide forms octahedral bis(tridentate) complexes with cobalt(III) and nickel(II), where the ligands are bound to the metal centres through deprotonated pyrrole and amide N atoms. N,N-Dibutyl-3,4-diphenyl-1H-pyrrole-2,5-dicarboxthioamide and N,N-diphenyl-3,4-diphenyl-1H-pyrrole-2,5-dicarboxthioamide also form bis(tridentate) cobalt complexes but are only deprotonated at the pyrrole N atom, the remainder of the coordination sphere comprising the thioamide S atoms. The dibutyl derivative was isolated as a Co(II) complex, whereas the diphenyl system deposited a Co(III) complex. In contrast, N,N-dibutyl-3,4-dichloro-1H-pyrrole-2,5-dicarboxamide was found to act as a bidentate ligand, in an octahedral cobalt(II) complex comprising of two bidentate pyrrole ligands, and two aqua ligands. Synthesis of N,N-bis(pyridin-2-ylmethyl)-3,4-diphenyl-1H-pyrrole-2,5-carboxamide gave a pyrrole ligand with increased denticity. Reaction with cobalt(II) chloride resulted in the isolation of a dinuclear helicate complex. The ligand was found to have undergone addition of a methoxy group to one of the linking methylene carbons, presumably as a result of the oxidative addition of solvent methanol.
0300-9246
4106-4112
Bates, Gareth W.
9b7c0c2e-76a1-4e20-870e-1fdbfeeaa36e
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Ogden, Mark I.
1461a54b-2593-4f78-98f3-69e77c316903
Warriner, Colin N.
2cdda67a-3408-4a5e-963c-8b0ee7555980
Bates, Gareth W.
9b7c0c2e-76a1-4e20-870e-1fdbfeeaa36e
Gale, Philip A.
c840b7e9-6847-4843-91af-fa0f8563d943
Light, Mark E.
cf57314e-6856-491b-a8d2-2dffc452e161
Ogden, Mark I.
1461a54b-2593-4f78-98f3-69e77c316903
Warriner, Colin N.
2cdda67a-3408-4a5e-963c-8b0ee7555980

Bates, Gareth W., Gale, Philip A., Light, Mark E., Ogden, Mark I. and Warriner, Colin N. (2008) Structural diversity in the first metal complexes of 2,5-dicarboxamidopyrroles and 2,5-dicarbothioamidopyrroles. Dalton Transactions, (31), 4106-4112. (doi:10.1039/b802506a).

Record type: Article

Abstract

Metal complexes of 2,5-dicarboxamidopyrroles and 2,5-dicarbothioamidopyrroles have been structurally characterised for the first time, complementing the significant amount of work that has been reported for the analogous pyridine ligands. N,N-Bis(3,5-dinitrophenyl)-3,4-diphenyl-1H-pyrrole-2,5-dicarboxamide forms octahedral bis(tridentate) complexes with cobalt(III) and nickel(II), where the ligands are bound to the metal centres through deprotonated pyrrole and amide N atoms. N,N-Dibutyl-3,4-diphenyl-1H-pyrrole-2,5-dicarboxthioamide and N,N-diphenyl-3,4-diphenyl-1H-pyrrole-2,5-dicarboxthioamide also form bis(tridentate) cobalt complexes but are only deprotonated at the pyrrole N atom, the remainder of the coordination sphere comprising the thioamide S atoms. The dibutyl derivative was isolated as a Co(II) complex, whereas the diphenyl system deposited a Co(III) complex. In contrast, N,N-dibutyl-3,4-dichloro-1H-pyrrole-2,5-dicarboxamide was found to act as a bidentate ligand, in an octahedral cobalt(II) complex comprising of two bidentate pyrrole ligands, and two aqua ligands. Synthesis of N,N-bis(pyridin-2-ylmethyl)-3,4-diphenyl-1H-pyrrole-2,5-carboxamide gave a pyrrole ligand with increased denticity. Reaction with cobalt(II) chloride resulted in the isolation of a dinuclear helicate complex. The ligand was found to have undergone addition of a methoxy group to one of the linking methylene carbons, presumably as a result of the oxidative addition of solvent methanol.

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Published date: August 2008

Identifiers

Local EPrints ID: 144963
URI: http://eprints.soton.ac.uk/id/eprint/144963
ISSN: 0300-9246
PURE UUID: 738ac81c-789e-49db-8dca-575af8250984
ORCID for Philip A. Gale: ORCID iD orcid.org/0000-0001-9751-4910
ORCID for Mark E. Light: ORCID iD orcid.org/0000-0002-0585-0843

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Date deposited: 15 Apr 2010 13:25
Last modified: 14 Mar 2024 02:44

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Contributors

Author: Gareth W. Bates
Author: Philip A. Gale ORCID iD
Author: Mark E. Light ORCID iD
Author: Mark I. Ogden
Author: Colin N. Warriner

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