Chemistry:8-Mercaptoquinoline
From HandWiki
8-Mercaptoquinoline is the organosulfur compound with the formula C9H7NSH. It is a derivative of the heterocycle quinoline, substituted in the 8-position with a thiol group. The compound is an analog of 8-hydroxyquinoline, a common chelating agent. In terms of physical properties, this compound crystallizes as a red solid dihydrate but the anhydrous compound is a blue liquid.[1][2]
8-Mercaptoquinoline functions as a bidentate ligand for many metal ions.[3]
Preparation
8-Mercaptoquinoline is usually prepared via quinoline-8-sulfonyl chloride. This species can be reduced with stannous chloride.[2] Triphenylphosphine has also been used as a reductant.[4]
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References
- ↑ Lee, H. S. (1963). "Novel Synthesis of 8-Mercaptoquinoline". Canadian Journal of Chemistry 41 (6): 1646–1647. doi:10.1139/v63-234. Bibcode: 1963CaJCh..41.1646L.
- ↑ 2.0 2.1 Corsini, Alfio.; Fernando, Quintus.; Freiser, Henry. (1963). "8-Mercaptoquinoline as an Analytical Reagent. Dissociation and Metal Chelate Formation Constants". Analytical Chemistry 35 (10): 1424–1428. doi:10.1021/ac60203a058.
- ↑ Fleischer, Holger "Structural chemistry of complexes of (n - 1)d10nsm metal ions with β-N-donor substituted thiolate ligands (m=0, 2)" Coordination Chemistry Reviews 2005, volume 249, pp. 799-827. doi:10.1016/j.ccr.2004.08.024
- ↑ Rao, Heng; Yu, Wen-Qian; Zheng, Hui-Qin; Bonin, Julien; Fan, Yao-Ting; Hou, Hong-Wei (2016). "Highly efficient photocatalytic hydrogen evolution from nickel quinolinethiolate complexes under visible light irradiation". Journal of Power Sources 324: 253–260. doi:10.1016/j.jpowsour.2016.05.095. ISSN 0378-7753. Bibcode: 2016JPS...324..253R.
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