Synthesis, structural characterization and DFT calculations of a new one-dimensional diorganotin(IV) derivative of N-isonicotinyl phosphoramide

Gholivand, Khodayar; Molaei, Foroogh; Rajabi, Maryam; Esrafili, Mehdi D.; Hosseini, Mahdieh

doi:10.1016/j.poly.2014.01.001

Cited by 25 publications

(19 citation statements)

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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%

“…The coordination chemistry of polyfunctional ligands such as pyridine carboxamides, which are capable of showing different coordination modes with metal cations, is of interest. In this regard, we reported the synthesis of a new series of N ‐nicotinyl (isonicotinyl) phosphoric triamide ligands, with the capacity of coordination from three donor sites (PO, CO and N py ), to study their ligation behaviour towards organotin(IV) compounds …”

Section: Introductionmentioning

confidence: 99%

“…In our previous studies, we have found that the reaction of SnCl 2 Me 2 with N ‐nicotinyl (isonicotinyl) phosphoric triamide ligands depends on the structure of the ligand in which the phosphorylated (iso)nicotinamides act as O ‐donor, N ‐donor or both forms . For example, the complexes of SnCl 2 Me 2 with 3‐C 5 H 4 NC(O)NHP(O)[NHC(CH) 3 ] 2 , 3‐NC 5 H 4 C(O)NHP(O)[NHC 6 H 11 ] 2 and 4‐NC 5 H 4 C(O)NHP(O)[NHC 6 H 11 ] 2 have been shown to exist as trans adducts with the PO donor site, whereas 4‐NC 5 H 4 C(O)NHP(O)[NHC(CH 3 ) 3 ] 2 acts as a N ‐donor ligand via the nitrogen atom of the pyridine ring (N py ) .…”

Section: Introductionmentioning

confidence: 99%

“…For example, the complexes of SnCl 2 Me 2 with 3‐C 5 H 4 NC(O)NHP(O)[NHC(CH) 3 ] 2 , 3‐NC 5 H 4 C(O)NHP(O)[NHC 6 H 11 ] 2 and 4‐NC 5 H 4 C(O)NHP(O)[NHC 6 H 11 ] 2 have been shown to exist as trans adducts with the PO donor site, whereas 4‐NC 5 H 4 C(O)NHP(O)[NHC(CH 3 ) 3 ] 2 acts as a N ‐donor ligand via the nitrogen atom of the pyridine ring (N py ) . Also, 4‐NC 5 H 4 C(O)NHP(O)(HNCHCH 3 C 6 H 5 ) 2 binds to Sn through N py and O P (the oxygen atom of phosphoryl group) in a trans–cis configuration . The strength of the Lewis basicity of the ligand (i.e.…”

Section: Introductionmentioning

confidence: 99%

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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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“…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%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

See 2 more Smart Citations

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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“…Moreover, the theoretical studies of the intermolecular N → Sn coordination in other organotin(IV) compounds are generally rare [43][44][45]. Therefore, the second goal of the present work is to provide insight into the intermolecular N → Sn coordination in the (Me 3 SnCN) 2 dimer.…”

Section: Introductionmentioning

confidence: 99%

Theoretical investigation of the N → Sn coordination in (Me3SnCN)2

Matczak

2014

Struct Chem

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The N → Sn coordination occurring in the (Me 3 SnCN) 2 dimer has been investigated using various computational methods and several theoretical tools possessing great interpretative potential. The dimer is formed by moving the C≡N fragment of the first Me 3 SnCN molecule close to the Sn atom of the second molecule and the resulting N → Sn coordination corresponds to that observed in the crystal structure of trimethyltin cyanide. The geometry of (Me 3 SnCN) 2 is optimized using the MP2 method and its 11 variants, and then it is compared with the reference geometry obtained at the CCSD level of theory. SCS-MP2 reproduces best the reference geometry of (Me 3 SnCN) 2 and its accuracy is close to that of the MP4 (SDQ) method. Two families of basis sets, namely the correlation-consistent basis sets proposed by Dunning and co-workers and the 'def2' basis sets developed by Ahlrichs and co-workers, are taken into account and their effect on the geometry of the dimer is examined in detail. The intermolecular interaction in (Me 3 SnCN) 2 has been analyzed using SAPT, NBO, QTAIM, and ELF. The results indicate that the (Me 3 SnCN) 2 dimer possesses a weak N → Sn coordination bond whose character is predominantly ionic. A value of −7.64 kcal/mol is proposed to be the best estimate of the interaction energy between the Me 3 SnCN molecules in the dimer.

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Ultrasonic‐assisted synthesis and biological evaluation of a nano‐rod diorganotin phosphonic diamide: Precursor for the fabrication of SnP₂O₇ nano‐structure

Dorosti

Delfan

Khodadadi

2017

Applied Organom Chemis

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{L = C 6 H 5 (O)P(NHC 6 H 11 ) 2 } have been synthesized by sonochemical processes at different concentrations without any surfactant or capping agent. The structure and morphology of the prepared complex were investigated by using SEM-EDAX, XRD, DLS, UV-Vis and FT-IR spectroscopy. Nanoparticles with well-defined rod shapes and sizes in the range 30-40 nm have been obtained. Also bulk form of the titled complex was synthesized and characterized by 1 H, 13 C, 31 P, 119 Sn NMR, UV-Vis and FT-IR spectroscopy and compared with its nano-size. The thermal stabilities at bulk and nano-size scale have been studied by thermal gravimetric (TG) and differential thermal analysis (DTA). Further, SnP 2 O 7 nanoparticles were synthesized by direct calcination at 730°C under air atmosphere and characterized using XRD, SEM, and TEM. From XRD measurements, we determined the mean size of the crystallites about 27.4 nm. It is found that the size and morphology of the tin pyrophosphate nano-structures are dependent upon the particles size of precursor compound as well. Two different forms of metal coordination compound (1a, 1b) and the corresponding ligand (L) were screened for their antibacterial activity against the selected Gram-positive and Gramnegative bacteria, showing bactericidal activity for complexes 1a and 1b. In vitro cytotoxicity of compounds was studied against human carcinoma cell lines, A2780 (ovarian cancer) and PC-3 (prostate cancer). Results indicated that 1a and 1b possess relatively strong cytotoxic activity against cancer cells with IC 50 values ranging from 93.2 to 376.2 μM for two exposure time (24 and 48 h).

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Synthesis, structural characterization and DFT calculations of a new one-dimensional diorganotin(IV) derivative of N-isonicotinyl phosphoramide

Cited by 25 publications

References 53 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

Theoretical investigation of the N → Sn coordination in (Me3SnCN)2

Ultrasonic‐assisted synthesis and biological evaluation of a nano‐rod diorganotin phosphonic diamide: Precursor for the fabrication of SnP₂O₇ nano‐structure

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Synthesis, structural characterization and DFT calculations of a new one-dimensional diorganotin(IV) derivative of N-isonicotinyl phosphoramide

Cited by 25 publications

References 53 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

Theoretical investigation of the N → Sn coordination in (Me3SnCN)2

Ultrasonic‐assisted synthesis and biological evaluation of a nano‐rod diorganotin phosphonic diamide: Precursor for the fabrication of SnP2O7 nano‐structure

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Ultrasonic‐assisted synthesis and biological evaluation of a nano‐rod diorganotin phosphonic diamide: Precursor for the fabrication of SnP₂O₇ nano‐structure