New organotin(IV) bromides containing potential donor ligands. Synthesis, characterization and supramolecular architecture

Someşan, Adrian-Alexandru; Varga, Richard A.; Silvestru, Cristian

doi:10.1016/j.ica.2017.09.066

Cited by 6 publications

(3 citation statements)

References 49 publications

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“…Interest in organotin compounds with C,Npendant arm ligands containing a sp 2 hybridized nitrogen, part of an imine functional group (C,N imine ), has increased in the last years. [1][2][3][4][5] These type of derivatives have been obtained, until recently, starting from a imine containing ligand either by ortho-lithiation of the ligand and subsequent reaction with tin derivatives [6][7][8] or orthometalation through rearrangement of benzylideneaminotin(IV) halides. 9,10 Derivatization of a carbonyl group from an organic moiety bonded to tin with different amines gives organotin(IV) compounds that can (i) stabilize unusual species, 1 (ii) coordinate to other metal centers through additional donor atoms or groups present in the parent amine 2,5 or (iii) result in homobimetallic derivatives by using diamines.…”

Section: Introduction *mentioning

confidence: 99%

“…[2-(1,1'-C 6 H 5 C 6 H 4 -4-N=CH)C 6 H 4 ]SnMe 2 Cl (1) was performed by mixing [2-(O=CH)C 6 H 4 ]SnMe 2 Cl 5 with (1,1'-biphenyl)-4-amine in the absence of a solvent or catalyst, as described previously for related organotin(IV) species. [1][2][3][4][5] Total conversion to the desired compound was confirmed by the 1 H NMR spectra of the crude product. Reaction of imine 1 with sodium sulfide gave the homobimetallic derivative 2.…”

Section: Introduction *mentioning

confidence: 99%

“…The solvent was removed in vacuo to obtain the compound as a yellow solid (0.1 g, 96 %), mp 227-229 °C. 1 H NMR (400.1 MHz, CDCl 3 , 20 °C): δ 0.83s (6H, H-16, 2 J SnH = 68.3/71.5 Hz), 7.32d (2H, H-9, 3 J HH = 8.5 Hz), 7.40t (1H, H-15, 3 J HH = 7.3 Hz), 7.48t (2H, H-14, 3 J HH = 7.6 Hz), 7.58td (1H, H-4,3 J HH = 7.4 Hz,4 J HH = 1.3 Hz), 7.62d (2H, H-13,3 J HH = 7 Hz), 7.69 two overlapped signals [7.69d (2H, H-10,3 J HH = 7.4 Hz); 7.69t (1H, H-5,3 J HH = 8.5 Hz)], 7.74d (1H, H-3,3 J HH = 7.5 Hz), 8.44d (1H, H-6, 3 J HH = 7.2 Hz, 3 J SnH 62.6 Hz), 8.69s (1H, H-7, 4 J SnH = 9.8 Hz) 13. C NMR (100.6 MHz, CDCl 3 , 20 °C): δ 2.17s (C-16, 1 J SnC = 524/548 Hz), 121.84s (C-9), 127.09s (C-13), 127.95s (C-15), 128.59s (C-10), 129.09s (C-14), 129.97s (C-4, 4 J SnC = 12.5 Hz), 132.40s (C-3, 3 J SnC = 49.4 Hz), 133.46s (C-5, 3 J SnC = 62.8 Hz), 138.04s (C-6, 2 J SnC = 37.5 Hz), 138.75s (C-2, 2 J SnC = 31.2 Hz), 139.87s (C-12), 141.05s (C-11), 143.52s (C-1), 145.76s (C-8), 163.69s (C-7, 3 J SnC = 20 .0 Hz).…”

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Synthesis and characterization of novel homobimetallic organotin(IV) compounds

Someşan¹,

Barbul²,

Vieriu³

et al. 2020

Rev.Roum.Chim.

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The (imino)aryltin(IV) chloride [2-(1,1'-C 6 H 5 C 6 H 4-4-N=CH)C 6 H 4 ]SnMe 2 Cl (1) was prepared by mixing [2-(O=CH)C 6 H 4 ]SnMe 2 Cl with (1,1'-biphenyl)-4amine in the absence of a solvent or catalyst. Reaction of 1 with sodium sulfide gave [{2-(1,1'-C 6 H 5 C 6 H 4-4-N=CH)C 6 H 4 }SnMe 2 ] 2 S (2). Treatment of 2 with ZnCl 2 or ZnSO 4 led to the isolation of the corresponding chloride (1) or sulfate [{2-(1,1'-C 6 H 5 C 6 H 4-4-N=CH)C 6 H 4 }SnMe 2 ] 2 SO 4 (3), respectively. All compounds were characterized in solution by multinuclear (1 H, 13 C and 119 Sn) NMR spectroscopy and mass spectrometry. In solid state, for all derivatives, IR spectroscopy confirms the presence of C=N double bonds, while singlecrystal X-ray diffraction analyses revealed the presence of pentacoordinated metal centers with a distorted trigonal bipyramidal geometry.

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Section: Introduction *mentioning

confidence: 99%

Section: Introduction *mentioning

confidence: 99%

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confidence: 99%

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Synthesis and characterization of novel homobimetallic organotin(IV) compounds

Someşan¹,

Barbul²,

Vieriu³

et al. 2020

Rev.Roum.Chim.

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C,O‐Chelated organotin(IV) derivatives as potential anticancer agents: Synthesis, characterization, and cytotoxic activity

Someşan

Vieriu

Crăciun

et al. 2022

Applied Organom Chemis

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Organotin(IV) chemistry is nowadays in a continuous expansion due to the biological and medicinal potential found for some of these species. Within this study, the cytotoxic activity of several organotin(IV) compounds was investigated on two lung cancer cell lines (H522 and SK‐MES‐1) and on a normal lung cell line in order to have an overview of the toxicity and the selectivity of these derivatives. Moreover, the synthetic protocols, as well as the structural particularities of the novel organotin(IV) species, are also discussed. Hydrolysis of [2‐{(CH2O)2CR}C6H4]2SnPh2 [R = H (1), Me (2)] with p‐toluenesulfonic acid as a proton source afford the expected derivatives [2‐(O═CR)C6H4]2SnPh2 [R = H (3), Me (4)]. When hydrochloric acid is used in these reactions, a chlorine‐phenyl exchange took place in addition to the removal of the acetal fragments and the following products [2‐(O═CR)C6H4]2SnPhCl [R = H (5), Me (6)] were isolated. Treatment of 5 with 2 equiv of 3‐aminomethylpyridine in neat affords the imino(aryl)tin compound 2‐(3′‐PyCH2N═CH)C6H4]2SnPhCl (7). The reaction between 6 and potassium nicotinate allows the isolation of the organotin(IV) carboxylate [2‐{O═C (CH3)}C6H4]2SnPh[O(O)CC5H4N‐3] (8). Compounds 1–8 were characterized by multinuclear NMR spectroscopy in solution, mass spectrometry, and IR spectroscopy, and their molecular structures were confirmed by X‐ray diffraction analysis. Compounds 1–8 were investigated for their antitumoral effects on Homo sapiens lung cancer cell lines (H522 and SK‐MES‐1) and on a normal bronchial epithelial cell line, BEAS‐2B.

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