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Convenient syntheses of cyanuric chloride-derived NHC ligands, their Ag(i) and Au(i) complexes and antimicrobial activity

Convenient syntheses of cyanuric chloride-derived NHC ligands, their Ag(i) and Au(i) complexes and antimicrobial activity
Convenient syntheses of cyanuric chloride-derived NHC ligands, their Ag(i) and Au(i) complexes and antimicrobial activity
Convenient syntheses of mono- and bis-imidazolium 1,3,5-triazine derivatives bearing piperidine and morpholine substituents are reported. In situ deprotonation of the mono-imidazolium salts and reaction with Ag2O or Au(tht)Cl (tht = tetrahydrothiophene) precursors affords the corresponding Ag(NHC) Cl and Au(NHC) Cl carbene complexes. In the presence of Ag(I) or Au(I) salts the bis-imidazolium pincers eliminate the imidazolium group to afford -OMe or -NMe2 substituted triazines depending on the solvent used. In solution, the Ag(I) and Au(I) complexes show a barrier to rotation about the C-triazine-N-amine bonds, with calculated Delta G(not equal) barriers in the region of 70 kJ mol(-1). Single crystal X-ray structures of several of the proligands and their corresponding Ag(I) and Au(I) complexes were obtained. These universally reveal an extended, rigidly planar pi-conjugated network between the triazine core, imidazolium/imidazolylidene substituents and exocyclic amine functions, to which the origin of the rotational barrier observed in solution is attributed. Only very weak N-triazine-metal interactions are observed in the solid state, as indicated by small deviations of the C-NHC-Ag-Cl bond angles from 180 degrees and also supported by DFT calculations on the Ag(NHC) Cl complex (NHC = 4,6-dipiperidinyl-2-methylimidazolylidene triazine). Preliminary antimicrobial susceptibility studies against five microorganisms (methicillin resistant Staphylococcus aureus NCTC 13277, S. aureus NCTC 6571, Pseudomonas aeruginosa NCTC 10662, Proteus mirabilis NCTC 11938 and Candida albicans ATCC 90028) show that the above triazine-based Ag-NHC complexes are active antimicrobial and antifungal agents.
1477-9226
12370-12380
Almalioti, Foteini
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MacDougall, James
0c04926a-a945-49f8-908b-3aa8189116a7
Hughes, Stephen
3e14ee79-db73-4e5a-8746-c7f3f30bfd84
Hasson, Mohammed M.
b3658db9-5bcb-417f-950b-cf856e8882e9
Jenkins, Robert L.
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Ward, Benjamin D.
3fe8307c-f34a-4469-97fc-2b335ed5fb7d
Tizzard, Graham J.
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Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Williams, David W.
2517b9b5-c6d8-4a7f-8794-61d0d90d553a
Bamford, Sarah
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Fallis, Ian A.
6f14a47a-a4f7-405d-94eb-33fe818a21c5
Dervisi, Athanasia
967db740-d11c-43a5-af7d-75a9eb5ad162
Almalioti, Foteini
89ee49b7-4960-4628-a3a2-8cef40abf10c
MacDougall, James
0c04926a-a945-49f8-908b-3aa8189116a7
Hughes, Stephen
3e14ee79-db73-4e5a-8746-c7f3f30bfd84
Hasson, Mohammed M.
b3658db9-5bcb-417f-950b-cf856e8882e9
Jenkins, Robert L.
7c9a06ba-1439-40e2-a412-7f22697d8280
Ward, Benjamin D.
3fe8307c-f34a-4469-97fc-2b335ed5fb7d
Tizzard, Graham J.
8474c0fa-40df-43a6-a662-7f3c4722dbf2
Coles, Simon J.
3116f58b-c30c-48cf-bdd5-397d1c1fecf8
Williams, David W.
2517b9b5-c6d8-4a7f-8794-61d0d90d553a
Bamford, Sarah
f90b49d1-0085-47df-9260-cd2a7b698987
Fallis, Ian A.
6f14a47a-a4f7-405d-94eb-33fe818a21c5
Dervisi, Athanasia
967db740-d11c-43a5-af7d-75a9eb5ad162

Almalioti, Foteini, MacDougall, James, Hughes, Stephen, Hasson, Mohammed M., Jenkins, Robert L., Ward, Benjamin D., Tizzard, Graham J., Coles, Simon J., Williams, David W., Bamford, Sarah, Fallis, Ian A. and Dervisi, Athanasia (2013) Convenient syntheses of cyanuric chloride-derived NHC ligands, their Ag(i) and Au(i) complexes and antimicrobial activity. Dalton Transactions, 42 (34), 12370-12380. (doi:10.1039/c3dt51400e).

Record type: Article

Abstract

Convenient syntheses of mono- and bis-imidazolium 1,3,5-triazine derivatives bearing piperidine and morpholine substituents are reported. In situ deprotonation of the mono-imidazolium salts and reaction with Ag2O or Au(tht)Cl (tht = tetrahydrothiophene) precursors affords the corresponding Ag(NHC) Cl and Au(NHC) Cl carbene complexes. In the presence of Ag(I) or Au(I) salts the bis-imidazolium pincers eliminate the imidazolium group to afford -OMe or -NMe2 substituted triazines depending on the solvent used. In solution, the Ag(I) and Au(I) complexes show a barrier to rotation about the C-triazine-N-amine bonds, with calculated Delta G(not equal) barriers in the region of 70 kJ mol(-1). Single crystal X-ray structures of several of the proligands and their corresponding Ag(I) and Au(I) complexes were obtained. These universally reveal an extended, rigidly planar pi-conjugated network between the triazine core, imidazolium/imidazolylidene substituents and exocyclic amine functions, to which the origin of the rotational barrier observed in solution is attributed. Only very weak N-triazine-metal interactions are observed in the solid state, as indicated by small deviations of the C-NHC-Ag-Cl bond angles from 180 degrees and also supported by DFT calculations on the Ag(NHC) Cl complex (NHC = 4,6-dipiperidinyl-2-methylimidazolylidene triazine). Preliminary antimicrobial susceptibility studies against five microorganisms (methicillin resistant Staphylococcus aureus NCTC 13277, S. aureus NCTC 6571, Pseudomonas aeruginosa NCTC 10662, Proteus mirabilis NCTC 11938 and Candida albicans ATCC 90028) show that the above triazine-based Ag-NHC complexes are active antimicrobial and antifungal agents.

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Published date: 2013
Organisations: Organic Chemistry: Synthesis, Catalysis and Flow, Chemistry, Faculty of Natural and Environmental Sciences

Identifiers

Local EPrints ID: 362485
URI: http://eprints.soton.ac.uk/id/eprint/362485
ISSN: 1477-9226
PURE UUID: a1614546-09ac-4813-87eb-8cb8889ce5ce
ORCID for Graham J. Tizzard: ORCID iD orcid.org/0000-0002-1577-5779
ORCID for Simon J. Coles: ORCID iD orcid.org/0000-0001-8414-9272

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Date deposited: 25 Feb 2014 13:42
Last modified: 18 Feb 2021 16:57

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Contributors

Author: Foteini Almalioti
Author: James MacDougall
Author: Stephen Hughes
Author: Mohammed M. Hasson
Author: Robert L. Jenkins
Author: Benjamin D. Ward
Author: Simon J. Coles ORCID iD
Author: David W. Williams
Author: Sarah Bamford
Author: Ian A. Fallis
Author: Athanasia Dervisi

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