The importance of Au⋯π(aryl) interactions in the formation of spherical aggregates in binuclear phosphane gold(I) complexes of a bipodal thiocarbamate dianion: a combined crystallographic and computational study, and anti-microbial activity
Binuclear phosphane gold(I) complexes of a bipodal thiocarbamate dianion, (R3PAu)2L, R = Et (1), Ph (2) and Cy (3), where LH2 is {1,4-[MeOC([double bond, length as m-dash]S)N(H)]2C6H4}, have been synthesised, and characterised spectroscopically (NMR and IR) and by X-ray crystallography. The gold ato...
| Main Authors: | , , , , , , , , , , , , |
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| Format: | Article |
| Language: | English |
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Royal Society of Chemistry
2015
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| Online Access: | http://psasir.upm.edu.my/id/eprint/46624/1/The%20importance%20of%20Au%E2%8B%AF%CF%80%28aryl%29%20interactions%20in%20the%20formation%20of%20spherical%20aggregates%20in%20binuclear%20phosphane%20gold%28I%29%20complexes%20of%20a%20bipodal%20thiocarbamate%20dianion%20a%20combined%20crystallographic%20and%20computational%20study%2C%20and%20anti-micro.pdf |
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| author | Chien, Ing Yeo Chai, Hoon Khoo Wern, Cui Chu Bao, Jing Chen Pek, Lim Chu Jiun, Horng Sim Yoke, Kqueen Cheah Ahmad, Jimmy Abdul Halim, Siti Nadiah Hoi, Ling Seng Soon, Ng Roza, A. Otero de la Tiekink, Edward R. T. |
| author_facet | Chien, Ing Yeo Chai, Hoon Khoo Wern, Cui Chu Bao, Jing Chen Pek, Lim Chu Jiun, Horng Sim Yoke, Kqueen Cheah Ahmad, Jimmy Abdul Halim, Siti Nadiah Hoi, Ling Seng Soon, Ng Roza, A. Otero de la Tiekink, Edward R. T. |
| author_sort | Chien, Ing Yeo |
| collection | UPM |
| description | Binuclear phosphane gold(I) complexes of a bipodal thiocarbamate dianion, (R3PAu)2L, R = Et (1), Ph (2) and Cy (3), where LH2 is {1,4-[MeOC([double bond, length as m-dash]S)N(H)]2C6H4}, have been synthesised, and characterised spectroscopically (NMR and IR) and by X-ray crystallography. The gold atoms are linearly coordinated within a P-,S-donor set, and are oriented toward the central ring to form intramolecular Au⋯π(aryl) interactions, rather than the intramolecular Au⋯O interactions normally observed in mononuclear analogues. This phenomenon has been investigated by theory (LC-ωPBE-XDM) for 1 which revealed that the geometry optimised species with two Au⋯π(aryl) interactions is more stable by at least 12 kcal mol−1 compared to conformations having one or more Au⋯O interactions instead. The disk diffusion, minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) methods were used to observe the inhibitory effect of complexes 1–3. The disk diffusion results demonstrated that 1 exhibited a broad spectrum of anti-bacterial activity toward 24 strains of Gram-positive and Gram-negative bacteria. By contrast, the anti-bacterial activity of 2 and 3 was limited to Gram-positive bacteria. Further evaluation showed that 1 exhibited marked bactericidal activity against B. cereus, B. subtilis, E. faecalis, L. monocytogenes, S. aureus, S. saprophyticus and methicillin resistant S. aureus cf. standard antibiotics tetracycline and chloramphenicol. |
| first_indexed | 2024-03-06T09:00:49Z |
| format | Article |
| id | upm.eprints-46624 |
| institution | Universiti Putra Malaysia |
| language | English |
| last_indexed | 2024-03-06T09:00:49Z |
| publishDate | 2015 |
| publisher | Royal Society of Chemistry |
| record_format | dspace |
| spelling | upm.eprints-466242018-02-23T04:35:11Z http://psasir.upm.edu.my/id/eprint/46624/ The importance of Au⋯π(aryl) interactions in the formation of spherical aggregates in binuclear phosphane gold(I) complexes of a bipodal thiocarbamate dianion: a combined crystallographic and computational study, and anti-microbial activity Chien, Ing Yeo Chai, Hoon Khoo Wern, Cui Chu Bao, Jing Chen Pek, Lim Chu Jiun, Horng Sim Yoke, Kqueen Cheah Ahmad, Jimmy Abdul Halim, Siti Nadiah Hoi, Ling Seng Soon, Ng Roza, A. Otero de la Tiekink, Edward R. T. Binuclear phosphane gold(I) complexes of a bipodal thiocarbamate dianion, (R3PAu)2L, R = Et (1), Ph (2) and Cy (3), where LH2 is {1,4-[MeOC([double bond, length as m-dash]S)N(H)]2C6H4}, have been synthesised, and characterised spectroscopically (NMR and IR) and by X-ray crystallography. The gold atoms are linearly coordinated within a P-,S-donor set, and are oriented toward the central ring to form intramolecular Au⋯π(aryl) interactions, rather than the intramolecular Au⋯O interactions normally observed in mononuclear analogues. This phenomenon has been investigated by theory (LC-ωPBE-XDM) for 1 which revealed that the geometry optimised species with two Au⋯π(aryl) interactions is more stable by at least 12 kcal mol−1 compared to conformations having one or more Au⋯O interactions instead. The disk diffusion, minimum inhibitory concentration (MIC) and minimum bactericidal concentration (MBC) methods were used to observe the inhibitory effect of complexes 1–3. The disk diffusion results demonstrated that 1 exhibited a broad spectrum of anti-bacterial activity toward 24 strains of Gram-positive and Gram-negative bacteria. By contrast, the anti-bacterial activity of 2 and 3 was limited to Gram-positive bacteria. Further evaluation showed that 1 exhibited marked bactericidal activity against B. cereus, B. subtilis, E. faecalis, L. monocytogenes, S. aureus, S. saprophyticus and methicillin resistant S. aureus cf. standard antibiotics tetracycline and chloramphenicol. Royal Society of Chemistry 2015 Article PeerReviewed text en http://psasir.upm.edu.my/id/eprint/46624/1/The%20importance%20of%20Au%E2%8B%AF%CF%80%28aryl%29%20interactions%20in%20the%20formation%20of%20spherical%20aggregates%20in%20binuclear%20phosphane%20gold%28I%29%20complexes%20of%20a%20bipodal%20thiocarbamate%20dianion%20a%20combined%20crystallographic%20and%20computational%20study%2C%20and%20anti-micro.pdf Chien, Ing Yeo and Chai, Hoon Khoo and Wern, Cui Chu and Bao, Jing Chen and Pek, Lim Chu and Jiun, Horng Sim and Yoke, Kqueen Cheah and Ahmad, Jimmy and Abdul Halim, Siti Nadiah and Hoi, Ling Seng and Soon, Ng and Roza, A. Otero de la and Tiekink, Edward R. T. (2015) The importance of Au⋯π(aryl) interactions in the formation of spherical aggregates in binuclear phosphane gold(I) complexes of a bipodal thiocarbamate dianion: a combined crystallographic and computational study, and anti-microbial activity. RSC Advances, 5 (1). pp. 41401-41411. ISSN ESSN: 2046-2069 http://pubs.rsc.org/en/journals/journalissues/ra 10.1039/c5ra05604g |
| spellingShingle | Chien, Ing Yeo Chai, Hoon Khoo Wern, Cui Chu Bao, Jing Chen Pek, Lim Chu Jiun, Horng Sim Yoke, Kqueen Cheah Ahmad, Jimmy Abdul Halim, Siti Nadiah Hoi, Ling Seng Soon, Ng Roza, A. Otero de la Tiekink, Edward R. T. The importance of Au⋯π(aryl) interactions in the formation of spherical aggregates in binuclear phosphane gold(I) complexes of a bipodal thiocarbamate dianion: a combined crystallographic and computational study, and anti-microbial activity |
| title | The importance of Au⋯π(aryl) interactions in the formation of spherical aggregates in binuclear phosphane gold(I) complexes of a bipodal thiocarbamate dianion: a combined crystallographic and computational study, and anti-microbial activity |
| title_full | The importance of Au⋯π(aryl) interactions in the formation of spherical aggregates in binuclear phosphane gold(I) complexes of a bipodal thiocarbamate dianion: a combined crystallographic and computational study, and anti-microbial activity |
| title_fullStr | The importance of Au⋯π(aryl) interactions in the formation of spherical aggregates in binuclear phosphane gold(I) complexes of a bipodal thiocarbamate dianion: a combined crystallographic and computational study, and anti-microbial activity |
| title_full_unstemmed | The importance of Au⋯π(aryl) interactions in the formation of spherical aggregates in binuclear phosphane gold(I) complexes of a bipodal thiocarbamate dianion: a combined crystallographic and computational study, and anti-microbial activity |
| title_short | The importance of Au⋯π(aryl) interactions in the formation of spherical aggregates in binuclear phosphane gold(I) complexes of a bipodal thiocarbamate dianion: a combined crystallographic and computational study, and anti-microbial activity |
| title_sort | importance of au⋯π aryl interactions in the formation of spherical aggregates in binuclear phosphane gold i complexes of a bipodal thiocarbamate dianion a combined crystallographic and computational study and anti microbial activity |
| url | http://psasir.upm.edu.my/id/eprint/46624/1/The%20importance%20of%20Au%E2%8B%AF%CF%80%28aryl%29%20interactions%20in%20the%20formation%20of%20spherical%20aggregates%20in%20binuclear%20phosphane%20gold%28I%29%20complexes%20of%20a%20bipodal%20thiocarbamate%20dianion%20a%20combined%20crystallographic%20and%20computational%20study%2C%20and%20anti-micro.pdf |
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