Tris-(1-methylimidazoline-2(3H)-thione)copper(I) nitrate: Preparation, thermal analysis and crystal structure

Atkinson, Edward R.; Gardiner, Derek J.; Jackson, Andrew; Raper, Eric S.

doi:10.1016/s0020-1693(00)90747-3

Cited by 51 publications

(9 citation statements)

References 14 publications

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“…1 and selected geometric parameters are given in (Beheshti et al, 2001). The Cu1ÐS1ÐC1 angle is essentially the same as those obtained for the terminal Hmimt ligand in [Cu(Hmim) 3 ](NO 3 ) (average 107.3 ; Atkinson et al, 1985). The bending at the thione S atom introduces an asymmetry in the anion which is also apparent in the dimensions of the WS 2 CuS core.…”

Section: Commentsupporting

confidence: 62%

Tetraethylammonium [1-methylimidazole-2(3H)-thione]copper(I)-di-μ-sulfido-dioxotungstate(VI)

et al. 2004

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In the title complex, tetrethylammonium [1‐methylimidazole‐2(3H)‐thione‐2κS]dioxo‐1κ2O‐di‐μ‐sulfido‐1:2κ4S:S‐copper(I)tungstate(VI), (C8H20N)[WCuO2S2(Hmimt)], where Hmimt is 1‐methylimidazole‐2(3H)‐thione (C4H6N2S), the W and Cu atoms have tetrahedral and trigonal planar coordination, respectively. Two sulfide ligands bridge the two metal centres; tungsten is additionally coordinated by two terminal oxo ligands and copper by the exocyclic S atom of Hmimt. The bridged W⋯Cu distance is 2.670 (3) Å. Anions are linked into chains by N—H⋯O hydrogen bonds between Hmimt and oxo ligands.

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Section: Commentsupporting

confidence: 62%

Tetraethylammonium [1-methylimidazole-2(3H)-thione]copper(I)-di-μ-sulfido-dioxotungstate(VI)

et al. 2004

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“…calcd for Hmim ArCl3 : C,38.7;H,1.8;N,10.0. Found: C,38.3;H,1.7;N,9.8. 1 H NMR (Me 2 SO-d 6 ): H 2 detu Ar(OMe)3 .…”

Section: X-ray Structure Determinationsmentioning

confidence: 99%

“…calcd for H 2 detu Ar(OMe)3 : C,53.6;H,7.3;N,7.8. Found: C,53.4;H,7.1;N,7.7. 1 H NMR (Me 2 SO-d 6 ): d 1.13 [t, 3 J H-H = 7, 6H of Hmim Ar(OMe)3 .…”

Section: X-ray Structure Determinationsmentioning

confidence: 99%

“…calcd for H 2 detu ArOMe,NO2 : C, 49.0; H, 6.2; N, 12.2. Found: C,49.1;H,6.1;N,12. 3.85 [s, 3H of C 6 H 3 (NO 2 )(OCH 3 )], 4.66 [t, 3 J H-H = 5, 1H of C(H)(OCH 2 CH 3 ) 2 ], 7.27 [dd, 3 J H-H = 9, 4 J H-H = 3, 1H of C 6 H 3 (NO 2 )(OCH 3 )], 7.49 [d, 4 J H-H = 3, 1H of C 6 H 3 (NO 2 )(OCH 3 )], 7.57 [d, 3 J H-H = 9, 1H of C 6 H 3 (NO 2 )(OCH 3 )], 8.13 [m, 1H of Hmim ArOMe,NO2 . A rapidly stirred solution of H 2 detu ArOMe,NO2 (27.1 g, 79 mmol) in a mixture of EtOH : H 2 O (300 mL, 9 : 1) was treated with HCl aq (6.0 mL of 12.1 M, 73 mmol).…”

Section: X-ray Structure Determinationsmentioning

confidence: 99%

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Synthesis and structural characterization of 1-arylimidazole-2-thiones and N,N′-aryldiethoxyethylthioureas with electronically diverse substituents: a manifold of hydrogen bonding networks

Palmer

Parkin

2014

New J. Chem.

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The 1-arylimidazole-2-thiones, (HmimAr) [Ar = 3,4,5-C6H2(OMe)3, 2,4-C6H3(NO2)(OMe), 2,4,6-C6H2Cl3 and 3,5-C6H3(CF3)2], which feature electronically diverse substituents, may be obtained via acid-catalyzed ring closure of the corresponding N,N′-aryldiethoxyethylthiourea derivatives, ArN(H)C(S)N(H)CH2CH(OEt)2, (H2detuAr), which in turn are obtained via treatment of aminoacetaldehyde diethyl acetal, H2NCH2CH(OEt)2, with the respective arylisothiocyanates (ArNCS). The molecular structures of all of the above N,N′-aryldiethoxyethylthioureas and 1-arylimidazole-2-thiones have been determined by X-ray diffraction, thereby demonstrating that the substituents have a profound effect on the crystal structures. For example, each of the N,N′-aryldiethoxyethylthiourea derivatives adopts a different hydrogen bonding pattern. Specifically, the hydrogen-bonding network in (i) H2detuArCl3 consists of chains of 9-membered rings, with an [ R22(9)] motif, that feature one N–H ⋯ O and one N–H ⋯ S interaction, (ii) H2detuArOMe,NO2 consists of chains of 6-membered rings, with an [ R21(6)] motif, that feature two head-to-tail N–H ⋯ S interactions, (iii) H2detuAr(CF3)2 consists of a dimer that features two pairs of N–H ⋯ O interactions, of which each pair is a component of an 8-membered ring with an [ R22(8)] motif, and (iv) H2detuAr(OMe)3 consists of a chain of head-to-head dimeric rings with a basic [ R22(16)] motif, a notable feature of which is that sulfur does not play a role as a hydrogen bond acceptor. Each of the 1-arylimidazole-2-thiones exists as a “head-to-head” hydrogen-bonded dimer in the solid state, with an [ R22(8)] motif. However, while the hydrogen-bonded motifs for HmimArCl3 and HmimAr(OMe)3 are planar, those for HmimAr(CF3)2 and HmimArOMe,NO2 are extremely puckered, with fold angles of 24.2° (mean value) and 45.7°, respectively.

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“…The 63Cu N Q R frequency of A, Cu(m im th)3N 0 3, which has a m ononuclear three-coordinated struc ture, [15], is 32.549 M Hz while those B, C u2(mimth)5S 0 4 -3 H 20 , where one of the five sul phur ligands bridges the two three coordinated copper atoms in the binuclear complex cation [16], are 27.926, and 27.285 M Hz [14], It may therefore be anticipated that a three-coordinated thione complex with two bridging ligands would have a resonance frequency as low as 22.5 MHz. The effect of changing the non bridging ligand to an arom atic amine can be esti mated as an increase of about 4.0 M Hz from the fact that the frequencies of three-coordinated complex cations analogous to A, where the ligand is a substi tuted pyridine molecule such as 2,6-lutidine, are in the range 4 2 -4 6 M Hz [3], The frequencies observed here are thus roughly those that would be expected.…”

Section: Nqrmentioning

confidence: 99%

Crystal Structure and NQR of Two Copper (I) Complexes of 4,6-Dimethylpyrimidine-2-thione

Ramaprabhu

Lücken

Bérnardinelli

1994

Zeitschrift Für Naturforschung A

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Tris-(1-methylimidazoline-2(3H)-thione)copper(I) nitrate: Preparation, thermal analysis and crystal structure

Cited by 51 publications

References 14 publications

Tetraethylammonium [1-methylimidazole-2(3H)-thione]copper(I)-di-μ-sulfido-dioxotungstate(VI)

Tetraethylammonium [1-methylimidazole-2(3H)-thione]copper(I)-di-μ-sulfido-dioxotungstate(VI)

Synthesis and structural characterization of 1-arylimidazole-2-thiones and N,N′-aryldiethoxyethylthioureas with electronically diverse substituents: a manifold of hydrogen bonding networks

Crystal Structure and NQR of Two Copper (I) Complexes of 4,6-Dimethylpyrimidine-2-thione

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