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An organomercury enzyme activator as a versatile template for new organomercury(II) compounds encompassing homobimetallic (RHg/Hg) and heterobimetallic (RHg/Cd) compositions: Syntheses, photoluminescence and structures


Basu Baul, Tushar S; Longkumer, Imliwati; Linden, Anthony (2014). An organomercury enzyme activator as a versatile template for new organomercury(II) compounds encompassing homobimetallic (RHg/Hg) and heterobimetallic (RHg/Cd) compositions: Syntheses, photoluminescence and structures. Journal of Organometallic Chemistry, 761:156-168.

Abstract

A series of pale yellow imine-functionalized acetyloxy(4-(arylideneamino)phenyl)mercury(II) compounds (2-7) were obtained by the reactions of acetyloxy(4-aminophenyl)mercury(II) (1) with arylaldehydes in equimolar ratios in absolute ethanol under reflux conditions. Organomercury compounds 2-5 and 7, when treated with 1,5-diphenylthiocarbazone (dptc) in chloroform, formed dark-red (4-((E)-arylideneamino)phenyl)(((Z)-((E)-phenyldiazenyl) (2-phenylhydrazono)methyl)thio)mercury compounds (8e12) in alkaline medium. The reaction of 7 with a slight excess of mercuric chloride in anhydrous methanol led to the formation of the bimetallic compound (2-{[4-(acetyloxymercuryl)phenyl]iminomethyl} pyridine-k2N,N0)dichloromercury(II) (7$HgCl2 ¼ 13). Homobimetallic compound 18 can be obtained from the reaction of the organomercurio-ligand precursor, 2-[((4-chloromercuryl)phenyl) iminomethyl]pyridine (15) with HgCl2, followed by crystallization from DMSO. Analogous DMF adducted mercury(II) and cadmium(II) compounds, 19 and 20, were also synthesized from the reaction of (15) with MCl2 (M = Hg or Cd) when crystallized from DMF. These reactions gave access to novel bimetallic iminefunctionalized chloro-compounds. The compounds were characterized by elemental analysis, and IR and 1H NMR spectroscopic studies. The solution state photophysical properties are also reported. The crystal structures of a polymeric organomercury compound (1)n, a dimeric imine-functionalized organomercury compound (3)2, a polymeric organomercurio-ligand (15)n, homobimetallic organomercury/mercury mixed compounds (18)n and (19)n, and a heterobimetallic organomercury/cadmium mixed compound (20)n are reported along with their supramolecular motifs.

Abstract

A series of pale yellow imine-functionalized acetyloxy(4-(arylideneamino)phenyl)mercury(II) compounds (2-7) were obtained by the reactions of acetyloxy(4-aminophenyl)mercury(II) (1) with arylaldehydes in equimolar ratios in absolute ethanol under reflux conditions. Organomercury compounds 2-5 and 7, when treated with 1,5-diphenylthiocarbazone (dptc) in chloroform, formed dark-red (4-((E)-arylideneamino)phenyl)(((Z)-((E)-phenyldiazenyl) (2-phenylhydrazono)methyl)thio)mercury compounds (8e12) in alkaline medium. The reaction of 7 with a slight excess of mercuric chloride in anhydrous methanol led to the formation of the bimetallic compound (2-{[4-(acetyloxymercuryl)phenyl]iminomethyl} pyridine-k2N,N0)dichloromercury(II) (7$HgCl2 ¼ 13). Homobimetallic compound 18 can be obtained from the reaction of the organomercurio-ligand precursor, 2-[((4-chloromercuryl)phenyl) iminomethyl]pyridine (15) with HgCl2, followed by crystallization from DMSO. Analogous DMF adducted mercury(II) and cadmium(II) compounds, 19 and 20, were also synthesized from the reaction of (15) with MCl2 (M = Hg or Cd) when crystallized from DMF. These reactions gave access to novel bimetallic iminefunctionalized chloro-compounds. The compounds were characterized by elemental analysis, and IR and 1H NMR spectroscopic studies. The solution state photophysical properties are also reported. The crystal structures of a polymeric organomercury compound (1)n, a dimeric imine-functionalized organomercury compound (3)2, a polymeric organomercurio-ligand (15)n, homobimetallic organomercury/mercury mixed compounds (18)n and (19)n, and a heterobimetallic organomercury/cadmium mixed compound (20)n are reported along with their supramolecular motifs.

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Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:organomercury compounds, crystal structure
Language:English
Date:2014
Deposited On:16 May 2014 15:42
Last Modified:05 Apr 2016 17:51
Publisher:Elsevier
ISSN:0022-328X
Funders:University Grants Commission, New Delhi, India (F. No. 42-396/2013 (SR)), Centre of Advanced Study in Chemistry, Phase-I, Indo-Swiss Joint Research Programme, Joint Utilisation of Advanced Facilities (Grant No. JUAF 11,) TSBB, AL)
Publisher DOI:https://doi.org/10.1016/j.jorganchem.2014.03.025

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