Synthesis, characterizations and crystal structures of new organoantimony(V) complexes with various isomers of fluoromethylbenzoate ligands

Yin, Handong; Wen, Liyuan; Cui, Jichun; Li, Wenkuan

doi:10.1016/j.poly.2009.06.065

Cited by 23 publications

(3 citation statements)

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“…The Sb–O distances in organoantimony compounds are extremely variable, ranging from 1.935 Å in triphenylstibine oxide [37] to 2.506 Å in tetraphenylstibonium benzenesulphonate hydrate [38]. The Sb–O distances in complex 1 and 2 [Sb(1)–O(1 i ); 2.1524(14) Å, Sb(1)–O(1 i ); 2.1524(14) Å] ( 1 ) and [Sb(1)–O(1); 2.1410(12) Å, Sb(1)–O(11); 2.1228(13) Å] ( 2 ) are comparable to those, reported previously, in triarylantimony dicarboxylates (2.095(2)−2.185(2) Å) [21,39].…”

Section: Resultsmentioning

confidence: 99%

Novel Triphenylantimony(V) and Triphenylbismuth(V) Complexes with Benzoic Acid Derivatives: Structural Characterization, in Vitro Antileishmanial and Antibacterial Activities and Cytotoxicity against Macrophages

et al. 2014

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Two novel organoantimony(V) and two organobismuth(V) complexes of the type ML 2 were synthesized, with L = acetylsalicylic acid (HL1) or 3-acetoxybenzoic acid (HL2) and M = triphenylantimony(V) (M1) or triphenylbismuth(V) (M2 6010by elemental analysis, IR and NMR. Crystal structures of triphenylantimony(V) dicarboxylate complexes 1 and 2 were determined by single crystal X-ray diffraction. Structural analyses revealed that 1 and 2 adopt five-coordinated extremely distorted trigonal bipyramidal geometries, binding with three phenyl groups in the equatorial position and two deprotonated organic ligands (L) in the axial sites. The metal complexes, their metal salts and ligands were evaluated in vitro for their activities against Leishmania infantum and amazonensis promastigotes and Staphylococcus aureus and Pseudomonas aeruginosa bacteria. Both the metal complexes showed antileishmanial and antibacterial activities but the bismuth complexes were the most active. Intriguingly, complexation of organobismuth(V) salt reduced its activity against Leishmania, but increased it against bacteria. In vitro cytotoxic test of these complexes against murine macrophages showed that antimony(V) complexes were the least toxic. Considering the selectivity indexes, organoantimony(V) complexes emerge as the most promising antileishmanial agents and organobismuth(V) complex 3 as the best antibacterial agent.

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Section: Resultsmentioning

confidence: 99%

Novel Triphenylantimony(V) and Triphenylbismuth(V) Complexes with Benzoic Acid Derivatives: Structural Characterization, in Vitro Antileishmanial and Antibacterial Activities and Cytotoxicity against Macrophages

et al. 2014

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“…Recently, the chemistry of antimony complexes derived from carboxylates has become an active area of research due to the biological perspective and their versatile bonding modes, the striking structural possibilities ranging from discrete monomeric structures to supramolecular assemblies (Yin et al 2009). As a part of our ongoing investigations in ths field we have synthesized the title compound and determined its crystal structure.…”

Section: S1 Commentmentioning

confidence: 99%

Bis(5-amino-2-chlorobenzoato-κO)triphenylantimony(V)

2009

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In the title compound, [Sb(C6H5)3(C7H5ClNO2)2], the Sb center has a distorted trigonal-bipyramidal geometry, with the O atoms of two carboxylate groups in axial positions and the C atoms of the phenyl groups in equatorial positions. Intramolecular C—H⋯O interactions occur. The molecules are connected by intermolecular N—H⋯O, N—H⋯N and C—H⋯O hydrogen-bonding interactions and C—H⋯π stacking interactions, forming a three-dimensional supramolecular framework

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“…Реакции дефенилирования пентафенилсурьмы карбоновыми кислотами лежат в основе эффективного метода синтеза карбоксилатов тетрафенилсурьмы Ph 4 SbOC(O)R [2 -28]. Эффективный способ синтеза карбоксилатов тетраарилсурьмы основан на реакции замещения атома галогена в галогениде тетраарилсурьмы на карбоксилатную группу [29,30]. Еще одним способом синтеза производных тетраарилсурьмы Ar 4 SbХ также является метод, основанный на реакции галогенида тетраарилсурьмы с соединениями, содержащими активный атом водорода, в присутствии амина [31,32].…”

Section: Introductionunclassified

Synthesis and Structure Features of Tetraphenylantimony 2,3-Difluoro- and 2,3,4,5,6-Pentafluorobenzoate

Ефремов¹

2020

Chem

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Tetraphenylantimony 2,3-difluorobenzoate (1) and tetraphenylantimony 2,3,4,5,6-pentafluorobenzoate (2) was obtained by the interaction of pentaphenylantimony with 2,3-difluorobenzoic and 2,3,4,5,6-pentafluorobenzoic acids in benzene with a yield of up to 98 %. The compounds were also synthesized by the ligand redistribution reaction between pentaphenylantimony and triphenylantimony dicarboxylates. The compounds have been identified by IR spectroscopy and X-ray diffraction analysis. According to the X-ray diffraction data, the antimony atoms in compounds 1 and 2 have a distorted trigonal-bipyramidal coordination with the oxygen atom in axial positions. X-ray diffraction analysis was performed on a D8 QUEST diffractometer (Bruker). The crystallographic parameters of the unit cell of the compounds: 1 space group Р1 ̅, а = 9.857(5), b = 10.154(7), c = 14.362(11) Å, α = 83.74(4)°, β = 82.59(3), γ = 68.34(2)°, V = 1321.9(16) Å3, ρcalc = 1.475 g/cm3, Z = 2; 2 space group Р21/с, а = 16.186(9), b = 8.771(6), c = 20.413(13) Å, α = 90.00°, β = 113.073(17), γ = 90.00°, V = 2666(3) Å3, ρcalc = 1.597 g/cm3, Z = 4. The OSbO axial angles are slightly different and amount to 177.90(5)º in 1 and 179.00(5)º in 2. The sums of the CSbC equatorial angles are 356.89(9)º (1), 355.85(7)º (2). The Sb–Ceq distances in compounds 1 and 2 are 2.116(2), 2.119(2), 2.118(2) and 2.1073(17), 2.1158(18), 2.1152(19) Å respectively, which are significantly shorter than the Sb–Сax bond lengths (2.169(2) and 2.1617(19) Å). The organization of molecules in the crystals of compounds is due to hydrogen bonds and CHπ-interactions of the aryl and carboxyl ligands. The main difference between structures 1 and 2 is the different Sb–O bond lengths (2.2864(18) and 2.3168(18) Å), which is due to an increase in the electronegativity of the carboxyl ligand in 2, caused by the presence of five electronegative fluorine atoms in the benzoate substituent. Complete tables of atom coordinates, bond lengths and valence angles are deposited at the Cambridge Crystallographic Data Center (No. 1980908 (1); 1977189 (2); deposit@ccdc.cam.ac.uk; http://www.ccdc.cam.ac.uk/data_request/cif).

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Synthesis, characterizations and crystal structures of new organoantimony(V) complexes with various isomers of fluoromethylbenzoate ligands

Cited by 23 publications

References 32 publications

Novel Triphenylantimony(V) and Triphenylbismuth(V) Complexes with Benzoic Acid Derivatives: Structural Characterization, in Vitro Antileishmanial and Antibacterial Activities and Cytotoxicity against Macrophages

Novel Triphenylantimony(V) and Triphenylbismuth(V) Complexes with Benzoic Acid Derivatives: Structural Characterization, in Vitro Antileishmanial and Antibacterial Activities and Cytotoxicity against Macrophages

Bis(5-amino-2-chlorobenzoato-κO)triphenylantimony(V)

Synthesis and Structure Features of Tetraphenylantimony 2,3-Difluoro- and 2,3,4,5,6-Pentafluorobenzoate

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