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 phosphanegold(i) complexes of a bipodal thiocarbamate dianion, (R3PAu)2L, R = Et (1), Ph (2) and Cy (3), where LH2 is {1,4-[MeOC(S)N(H)]2C6H4}, have been synthesised, and characterised spectroscopically (NMR and IR) and by X-ray crystallography. The gold atoms are linearly coordinated with...
Saved in:
Main Authors: | , , , , , , , , , , , , |
---|---|
Format: | Article |
Published: |
Royal Society of Chemistry
2015
|
Subjects: | |
Online Access: | http://eprints.um.edu.my/19375/ http://dx.doi.org/10.1039/C5RA05604G |
Tags: |
Add Tag
No Tags, Be the first to tag this record!
|
id |
my.um.eprints.19375 |
---|---|
record_format |
eprints |
spelling |
my.um.eprints.193752018-09-21T06:02:12Z http://eprints.um.edu.my/19375/ 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 Yeo, C.I. Khoo, C.H. Chu, W.C. Chen, B.J. Chu, P.L. Sim, J.H. Cheah, Y.K. Ahmad, J. Halim, S.N.A. Seng, H.L. Ng, S. Otero-de-la-Roza, A. Tiekink, E.R.T. Q Science (General) QD Chemistry QH Natural history R Medicine Binuclear phosphanegold(i) complexes of a bipodal thiocarbamate dianion, (R3PAu)2L, R = Et (1), Ph (2) and Cy (3), where LH2 is {1,4-[MeOC(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 Yeo, C.I. and Khoo, C.H. and Chu, W.C. and Chen, B.J. and Chu, P.L. and Sim, J.H. and Cheah, Y.K. and Ahmad, J. and Halim, S.N.A. and Seng, H.L. and Ng, S. and Otero-de-la-Roza, A. and Tiekink, E.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 (52). pp. 41401-41411. ISSN 2046-2069 http://dx.doi.org/10.1039/C5RA05604G doi:10.1039/C5RA05604G |
institution |
Universiti Malaya |
building |
UM Library |
collection |
Institutional Repository |
continent |
Asia |
country |
Malaysia |
content_provider |
Universiti Malaya |
content_source |
UM Research Repository |
url_provider |
http://eprints.um.edu.my/ |
topic |
Q Science (General) QD Chemistry QH Natural history R Medicine |
spellingShingle |
Q Science (General) QD Chemistry QH Natural history R Medicine Yeo, C.I. Khoo, C.H. Chu, W.C. Chen, B.J. Chu, P.L. Sim, J.H. Cheah, Y.K. Ahmad, J. Halim, S.N.A. Seng, H.L. Ng, S. Otero-de-la-Roza, A. Tiekink, E.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 |
description |
Binuclear phosphanegold(i) complexes of a bipodal thiocarbamate dianion, (R3PAu)2L, R = Et (1), Ph (2) and Cy (3), where LH2 is {1,4-[MeOC(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. |
format |
Article |
author |
Yeo, C.I. Khoo, C.H. Chu, W.C. Chen, B.J. Chu, P.L. Sim, J.H. Cheah, Y.K. Ahmad, J. Halim, S.N.A. Seng, H.L. Ng, S. Otero-de-la-Roza, A. Tiekink, E.R.T. |
author_facet |
Yeo, C.I. Khoo, C.H. Chu, W.C. Chen, B.J. Chu, P.L. Sim, J.H. Cheah, Y.K. Ahmad, J. Halim, S.N.A. Seng, H.L. Ng, S. Otero-de-la-Roza, A. Tiekink, E.R.T. |
author_sort |
Yeo, C.I. |
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_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_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_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 |
publisher |
Royal Society of Chemistry |
publishDate |
2015 |
url |
http://eprints.um.edu.my/19375/ http://dx.doi.org/10.1039/C5RA05604G |
_version_ |
1643690969402441728 |
score |
13.18916 |