Steric and electronic control over the structural diversity of N-(n-pyridinyl) diphenylphosphinic amides (n = 2 and 4) as difunctional ligands in triphenyltin(<scp>iv</scp>) adducts

Gholivand, Khodayar; Gholami, Akram; Tizhoush, Samaneh K.; Schenk, Kurt; Fadaei, Farzaneh T.; Bahrami, Aidin

doi:10.1039/c4ra06212d

Cited by 19 publications

(12 citation statements)

References 41 publications

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“…The Sn-C bond distances ( Table 2) are in a good agreement with the published values [15,17]. These values also correspond well with the sum of the covalent radii (2.15 Å) of tin and carbon [33].…”

Section: Synthesis and Spectroscopic Characterizationsupporting

confidence: 88%

Synthesis, characterization, crystal structures, QSAR study and antibacterial activities of organotin bisphosphoramidates

Gholivand

EbrahimiValmoozi

Gholami

et al. 2016

Journal of Organometallic Chemistry

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Section: Synthesis and Spectroscopic Characterizationsupporting

confidence: 88%

Synthesis, characterization, crystal structures, QSAR study and antibacterial activities of organotin bisphosphoramidates

Gholivand

EbrahimiValmoozi

Gholami

et al. 2016

Journal of Organometallic Chemistry

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“…11,22,23 Therefore, for having two coordinative sites on triphenyltin the Cl À ion would have to be dissociated. In other word, the steric demands of SnPh 3 Cl, due to the presence of three bulky phenyl groups on tin, lead to the formation of ve- coordinate complexes in most cases.…”

Section: Fully Optimized Structures In the Gas Phasementioning

confidence: 99%

“…From the above consideration, in connection with our current interest in the coordination of phosphoramidates, [6][7][8][9][10][11] we have further investigated the ligand behaviour of some bidentate P(O)-X-P(O) ligands toward SnPh 3 Cl. Our interest in this unique class of ligands stems from the systematic control of stereoelectronic factors by subtle manipulation of the central part (X), as well as terminal phosphorus substituents (R) in order to study the inuence on the structure and properties of the resulting complexes.…”

Section: Introductionmentioning

confidence: 99%

Triphenyltin(iv) adducts of diphosphoryl ligands: structural, electronic and energy aspects from X-ray crystallography and theoretical calculations

et al. 2015

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Some triphenyltin(IV) adducts with a family of diphosphoryl ligands, RR 0 P(O)-X-P(O)RR 0 (R ¼ OPh, Ph, R 0 ¼ R, An (aniline)) and X ¼ 1,4-OC 6 H 4 O, 1,4-OC 6 H 4 NH, 1,4-NHC 6 H 4 NH 1,4-(NHCH 2 ) 2 C 6 H 4 , 1,3-(NHCH 2 ) 2 C 6 H 4 and piperazine have been synthesized and characterized by IR and NMR spectroscopy. X-Ray crystallography reveals that the structure of these complexes comprises a binuclear arrangement with two SnPh 3 Cl moieties linked via the bridging P(O)-X-P(O) ligands. The influence of the ligand structures on the organization of the crystal structures and the coordination interactions are discussed. Studies of the crystal packing reveal NH/Cl, CH/Cl or CH/O hydrogen bonding interactions, as a function of the X or R groups, to be the main factor controlling the supramolecular architecture in this series of complexes. Based on the results from quantum theory of atoms in molecules (QTAIM) and natural bond orbital (NBO) analyses, Sn-ligand interactions are found to be mainly electrostatic (donor-acceptor-like with charge transfer from the phosphoryl donors to the tin atoms). The stronger coordination bonds are found in the complexes containing Ph substituents with aliphatic spacers, in agreement with the experimental evidence. Binuclear arrangements instead of polymeric or chelating systems may be attributed to the steric demands of SnPh 3 Cl, regardless of the ligand structures. † Electronic supplementary information (ESI) available: The crystal data and the details of the X-ray analysis, selected bond lengths, bond angles, hydrogen bonding data for the ligand 6Ph and computational data for fully optimized structures. CCDC 990940-990945. For ESI and crystallographic data in CIF or other electronic format see

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“…The coordination chemistry of organotin compounds has become of great interest because of their important applications as anticancer agents, agrochemical fungicides and biocides, as well as catalysts . Synthesis of organotin with phosphoramide ligands by the reaction of Sn(R) n Cl 4‐n ( n = 1–3) (R = Cl, CH 3 , C 6 H 5 ) with various phosphoramides, as well as evaluation of their cytotoxicity against some human cell lines and microbial strains have frequently been studied . Recently, the development of coordination complexes as nano‐structured materials has increased for nanotechnological applications because of their superior physical and chemical properties that cannot be observed in bulk counterparts.…”

Section: Introductionmentioning

confidence: 99%

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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Steric and electronic control over the structural diversity of N-(n-pyridinyl) diphenylphosphinic amides (n = 2 and 4) as difunctional ligands in triphenyltin(iv) adducts

Cited by 19 publications

References 41 publications

Synthesis, characterization, crystal structures, QSAR study and antibacterial activities of organotin bisphosphoramidates

Synthesis, characterization, crystal structures, QSAR study and antibacterial activities of organotin bisphosphoramidates

Triphenyltin(iv) adducts of diphosphoryl ligands: structural, electronic and energy aspects from X-ray crystallography and theoretical calculations

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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Steric and electronic control over the structural diversity of N-(n-pyridinyl) diphenylphosphinic amides (n = 2 and 4) as difunctional ligands in triphenyltin(iv) adducts

Cited by 19 publications

References 41 publications

Synthesis, characterization, crystal structures, QSAR study and antibacterial activities of organotin bisphosphoramidates

Synthesis, characterization, crystal structures, QSAR study and antibacterial activities of organotin bisphosphoramidates

Triphenyltin(iv) adducts of diphosphoryl ligands: structural, electronic and energy aspects from X-ray crystallography and theoretical calculations

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