A 3-D Mn(II) complex containing N-isonicotinyl, N′,N′′-bis(hexamethylenyl) phosphoric triamide ligand: synthesis, structural characterization, and thermal studies

Gholivand, Khodayar; Rajabi, Maryam; Molaei, Foroogh; Mahzouni, Hamid Reza; Farshadian, Sedigheh

doi:10.1080/00958972.2013.863879

Cited by 14 publications

(15 citation statements)

References 43 publications

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“…For organotin(IV) complexes of N ‐nicotinyl (isonicotinyl) phosphoric triamide ligands, IR spectroscopy can provide useful information concerning the coordination pattern of the ligand …”

Section: Resultsmentioning

confidence: 99%

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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“…For organotin(IV) complexes of N ‐nicotinyl (isonicotinyl) phosphoric triamide ligands, IR spectroscopy can provide useful information concerning the coordination pattern of the ligand …”

Section: Resultsmentioning

confidence: 99%

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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“…The ligand was prepared and purified according to the literature procedure from the reaction of hexamethyleneimine (4 mmol, 0.48 g) with 4‐NC 5 H 4 C(O)NHP(O)Cl 2 (1 mmol, 0.24 g) 13a . The amine was added dropwise to a CH 3 CN solution (40 ml) of 4‐NC 5 H 4 C(O)NHP(O)Cl 2 at 0 °C.…”

Section: Methodsmentioning

confidence: 99%

“…[ 12 ] Pyridinecarbacylamidophosphates (PCAPh) are phosphoramide derivatives with good pharmacological properties, which can assist in the formation of complexes and provide different coordination modes by O phosphoryl and N pyridine donor sites. [ 13 ] In our previous work, nanoparticles octahedral O ‐ligated 4‐PCAPh‐based tin (IV) complex was synthesized and the cholinesterase inhibitor activity was found. [ 14 ] Here we continue our study in this field, in particular to investigate the effect of size, and the choice of ligand and tin adducts on the ChE inhibitor activities of complexes based on pyridinecarbacylamidophosphate derivatives.…”

Section: Introductionmentioning

confidence: 99%

“…[ 14 ] Here we continue our study in this field, in particular to investigate the effect of size, and the choice of ligand and tin adducts on the ChE inhibitor activities of complexes based on pyridinecarbacylamidophosphate derivatives. 4‐PCAPh ligand, 4‐NC 5 H 4 C(O)NHP(O)(C 6 H 12 N) 2 ( L ), 13a was used to prepare two new organotin complexes SnCl 2 (CH 3 ) 2 L 2 ( C 1 ) and Sn(C 6 H 5 ) 3 ClL ( C 2 ). The complexes were characterized by 1 H, 13 C, 31 P NMR, IR spectroscopy and elemental analysis.…”

Section: Introductionmentioning

confidence: 99%

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Nano‐ and micro‐structure tin (IV) complexes bearing 4‐pyridinecarbacylamidophosphate: Sonochemical synthesis, crystal structure, anti‐cholinesterase activity, and docking studies

Nikpour

Dorosti

Afshar

et al. 2020

Applied Organom Chemis

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Two di-and triorganotin (IV) complexes, Sn (CH 3) 2 Cl 2 (4-PCAPh) 2 (C 1) and Sn(C 6 H 5) 3 Cl(4-PCAPh) (C 2); {4-PCAPh = 4-NC 5 H 4 C(O)NHP(O) (C 6 H 12 N) 2 }, have been synthesized and characterized by elemental analysis, 1 H, 13 C, 31 P NMR and IR spectroscopy. The crystal structure of C 1 has been confirmed by X-ray crystallography, which reveals an octahedral geometry surrounding Sn (IV). Both ligands function in an all-trans conformation, with an N-ligated mode for 4-PCAPh. Also, the complexes were prepared at nano-(C 1) and micro-size (C 2) by the sonochemical process. The role of reaction solvent and the concentration of initial reactants on the size and morphology of particles were studied and the products were characterized by X-ray powder diffraction (XRPD) and scanning electron microscopy (SEM). The activities and mechanism of complexes C 1 , C 2 , C 1 , C 2 and their corresponding ligand (L) on cholinesterase (ChE) were evaluated using a modified Ellman's method and Lineweaver-Burk plots. Nanosheet C 1 showed the best activity against AChE and BChE with the IC 50 values being 73.08 ± 0.12 μM and 122.48 ± 0.69 μM, respectively, and the mixed-type mechanism. Molecular modeling simulation revealed the binding interaction template for Sn (CH 3) 2 Cl 2 (4-PCAPh) 2 with the ChE.

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“…The crystal structure of three phosphorus hydrazide compounds based on methyl carbazate (1, 2, and 5) have been studied in detail by X-ray analysis to find out more about the differences in bonding characteristics, orientation of functional groups, and packing interactions. In most phosphoramides with the -P(O)-NH-C(O)-moiety, the anti orientation has been reported for PQO and CQO functionals, as a result of the electronic dipole-dipole repulsion, [27][28][29] and only for two of them the syn orientation has been observed. 1, and the detailed crystal data and selected structural parameters are summarized in Tables 2 and 3 presents an almost planar environment of these atoms, while N1 in 1 (355.721), N1 and N4 in 2 (347.1, 350.211) and N3 in 5 (349.061) show more deviation from planarity.…”

Section: Spectroscopic Studiesmentioning

confidence: 99%

Synthesis and structural study of some new phosphorus(v) hydrazide compounds: spectroscopic evidence and a theoretical approach

Gholivand

Molaei

2015

New J. Chem.

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New phosphorus(V) hydrazide compounds containing the [-P(O)NHNHC(O)OR] fragment have beenprepared by the reaction of mono-and di-chloro phosphoryl intermediates with methyl (R = CH 3 , 1-5) and tert-butyl (R = C(CH 3 ) 3 , 6-9) carbazates, and characterized by IR and multinuclear NMR spectroscopy.Molecular structures of 1, 2, and 5 have been established by X-ray diffraction analysis to investigate the relative orientation of the present moieties, resulting hydrogen bonding motifs and stabilizing intermolecular interactions. The impact of the intermolecular contacts on crystal packing has been further studied by Hirshfeld surface analysis. The dependence of experimental d 31 P and 2 J PNH values on phosphorus substituents has been explored using natural bond orbital (NBO) analysis. Likewise, the reasons for maintaining the tetrahedral geometry around the phosphorus atom in the synthesized compounds and not rearranging to a trigonal bipyramidal one (in comparison with spirophosphoranes) have been investigated theoretically. Overall, the NBO results reveal the influential role of electronic delocalization and s-content in hybridization for the above-mentioned experimental evidence.

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A 3-D Mn(II) complex containing N-isonicotinyl, N′,N′′-bis(hexamethylenyl) phosphoric triamide ligand: synthesis, structural characterization, and thermal studies

Cited by 14 publications

References 43 publications

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, 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

Nano‐ and micro‐structure tin (IV) complexes bearing 4‐pyridinecarbacylamidophosphate: Sonochemical synthesis, crystal structure, anti‐cholinesterase activity, and docking studies

Synthesis and structural study of some new phosphorus(v) hydrazide compounds: spectroscopic evidence and a theoretical approach

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