Synthesis and molecular structure of the all-trans- and the trans–cis-isomers of dichlorodimethyltin complexes of phosphoric triamides

Gholivand, Khodayar; Farshadian, Sedigheh

doi:10.1016/j.ica.2010.12.060

Cited by 24 publications

(18 citation statements)

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“…In trans position of the two oxygen atoms are chlorines and distances are correlated: the shorter is SneO, the longer is SneCl (perhaps 'trans effect'), in agreement with other organotin phosphoramidates [22].…”

Section: X-ray Crystallography Investigationsupporting

confidence: 75%

“…The NMR spectra of the ligands and complexes were recorded in non-coordinating solvent, CDCl 3 at room temperature. The chemical shifts and splitting of the CH(CH 3 ) 2 protons and carbons of ligands are quite similar to those observed for BeCAPhs [22] and are almost insensitive to complexation. However the NH amine chemical shifts in the spectra of 1e3 and 4e6 show an upfield shift relative to those of ligands and complexes with Nbenzoyl derivatives.…”

Section: Spectral Characterizationsupporting

confidence: 70%

“…Furthermore, the Cl(1) and Cl(2) chlorine atoms function as bifurcated acceptors and are involved in intramolecular hydrogen bonds with NH amidic groups forming six-membered [SneCl/HeNePeOe] rings similar to our previous reported organotin phosphoramidates [22]. On the other hand, each of them is linked to the NH amine group in a neighboring complex thus two hydrogen bonds of the DA ¼ AD type (A ¼ H bond acceptor and D ¼ H bond donor) are formed.…”

Section: X-ray Crystallography Investigationsupporting

confidence: 70%

“…Table 2, chemical shift of 31 P for compounds 1e3 are 5.41, 5.50 and 4.60 ppm, respectively and are shifted upfield upon complexation as observed before for the carbacylamidophosphate organotins. These signals are also upfield shifted relative to those in N-benzoyl derivatives [22].…”

Section: Spectral Characterizationmentioning

confidence: 90%

“…The solid state results showed the monomeric all-trans octahedral complexes due to the fewer steric hindrance in the trans geometry. Two transecis isomers were also obtained with the presence of CH 3 CN molecules in the crystal packing [22]. However, to our knowledge no organotin complexes of N-acetyl derivatives of carbacylamidophosphates (AeCAPh) are known.…”

Section: Introductionmentioning

confidence: 93%

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Diorganotin(IV) complexes of N-mono-, di- and tri-chloroacetyl, N′,N″-bis(isopropyl) phosphoric triamide

Gholivand¹,

Farshadian²,

Hosseini³

2012

Journal of Organometallic Chemistry

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Section: X-ray Crystallography Investigationsupporting

confidence: 75%

Section: Spectral Characterizationsupporting

confidence: 70%

Section: X-ray Crystallography Investigationsupporting

confidence: 70%

Section: Spectral Characterizationmentioning

confidence: 90%

Section: Introductionmentioning

confidence: 93%

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Diorganotin(IV) complexes of N-mono-, di- and tri-chloroacetyl, N′,N″-bis(isopropyl) phosphoric triamide

Gholivand¹,

Farshadian²,

Hosseini³

2012

Journal of Organometallic Chemistry

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Synthesis, structural characterization, density functional theory calculations and biological evaluation of a new organotin(IV) complex containing N‐isonicotinyl‐N',N″‐diaryl phosphorictriamide as N‐donor ligand

Gholivand

Rajabi

Dorosti

et al. 2015

Applied Organom Chemis

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A new diorganotin(IV) complex with the formula SnCl2(CH3)2L2 (C1a), L = 4‐NC5H4CONHPO(NCH3CH2C6H5)2, was synthesized and characterized using 1H NMR, 13C NMR, 31P NMR, 119Sn NMR and infrared spectroscopies. The molecular structure of C1a was determined using X‐ray crystallography, revealing that C1a contains hexa‐coordinated Sn(IV) centres with trans‐configuration of donor atoms around them. Each Sn(IV) atom is positioned in the centre of inversion of an octahedron. C1a forms one‐dimensional chains via two equal intermolecular PO…HN hydrogen bonds. These hydrogen bonds produce centrosymmetric rings as a supramolecular hydrogen‐bonded pattern. In order to compare the relative stability of C1a (with N‐ligated configuration) and its possible O‐ligated isomer, C1b, density functional theory calculations were performed, the results showing a preference of C1a over C1b from an energy point of view. Also, natural bond orbital analysis was carried out to obtain detailed information on the electronic features of the optimized structures. The theoretical results show that intermolecular hydrogen bonding in the crystal structure has a significant role in the stabilization of C1a, and Sn(IV) interacts more strongly with the Npy atom than the PO functional group. Furthermore, the free ligand and its complex were tested against three human cancer cell lines, i.e. human cervical carcinoma (HeLa), human prostate cancer (PC‐3) and human breast adenocarcinoma cancer (MCF‐7). C1a displays moderate to good cytotoxicity towards all three cancer cell lines. Moreover, antibacterial tests were carried out using the disc‐diffusion method, in which C1a shows high activity against selected Gram‐negative and Gram‐positive bacteria. Copyright © 2015 John Wiley & Sons, Ltd.

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Synthesis, characterization and biological evaluation of a nanorod five‐coordinated Sn(IV) complex. Theoretical studies of (CH₃)₂Sn(O₂PPh₂)₂

Dorosti

Mohammadpour

2018

Applied Organom Chemis

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A new five-coordinated diorganotin(IV) complex with formula Sn(CH 3 ) 2 Cl 2 L (L = (C 6 H 5 ) 2 (O)P(NHC 6 H 11 )), with a rod-shaped nanostructure, was synthesized using a sonochemical method. The nanostructure was characterized using various techniques. The bulk complex was also produced using a reflux method applied to a solution of the reagents. The ligand and bulk form were characterized using 1 H NMR, 13 C NMR, 31 P NMR, 119 Sn NMR, UV-visible and infrared spectroscopies. By direct calcination of the synthesized complex at 650°C, nanopowders were obtained with spherical-like structure and diameters of 40-100 nm (for bulk form) and 20-60 nm (for nanometric form). Two different forms of Sn(IV) complex (C 1 , C 2 ) and the corresponding ligand were evaluated regarding their anticancer activity, as well as their influence on both Gram-positive and Gram-negative classes of bacteria. Among the compounds, nanostructured C 2 was found to be the most active with IC 50 of 62 ± 0.03 and 92 ± 0.09 μM against A2780 and PC-3 cell lines. Preliminary antibacterial experiments were carried out using the cup test method, in which nanocomplex C 2 showed better activity against all the selected bacteria than other compounds. Moreover, single crystals of C 3 were obtained by the interaction of (CH 3 ) 2 Cl 2 Sn with L in ethanol-water solution, where the Sn(IV) ion is six-coordinated with one-dimensional polymeric chains. The intermolecular interactions which connected the chains into a two-dimensional framework were supported by Hirshfeld surface analysis and fingerprint plots.

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Synthesis and molecular structure of the all-trans- and the trans–cis-isomers of dichlorodimethyltin complexes of phosphoric triamides

Cited by 24 publications

References 45 publications

Diorganotin(IV) complexes of N-mono-, di- and tri-chloroacetyl, N′,N″-bis(isopropyl) phosphoric triamide

Diorganotin(IV) complexes of N-mono-, di- and tri-chloroacetyl, N′,N″-bis(isopropyl) phosphoric triamide

Synthesis, structural characterization, density functional theory calculations and biological evaluation of a new organotin(IV) complex containing N‐isonicotinyl‐N',N″‐diaryl phosphorictriamide as N‐donor ligand

Synthesis, characterization and biological evaluation of a nanorod five‐coordinated Sn(IV) complex. Theoretical studies of (CH₃)₂Sn(O₂PPh₂)₂

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Synthesis and molecular structure of the all-trans- and the trans–cis-isomers of dichlorodimethyltin complexes of phosphoric triamides

Cited by 24 publications

References 45 publications

Diorganotin(IV) complexes of N-mono-, di- and tri-chloroacetyl, N′,N″-bis(isopropyl) phosphoric triamide

Diorganotin(IV) complexes of N-mono-, di- and tri-chloroacetyl, N′,N″-bis(isopropyl) phosphoric triamide

Synthesis, structural characterization, density functional theory calculations and biological evaluation of a new organotin(IV) complex containing N‐isonicotinyl‐N',N″‐diaryl phosphorictriamide as N‐donor ligand

Synthesis, characterization and biological evaluation of a nanorod five‐coordinated Sn(IV) complex. Theoretical studies of (CH3)2Sn(O2PPh2)2

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Synthesis, characterization and biological evaluation of a nanorod five‐coordinated Sn(IV) complex. Theoretical studies of (CH₃)₂Sn(O₂PPh₂)₂