Multinuclear NMR and crystallographic studies of triorganotin valproates and their in vitro antifungal activities

Morais, B.P. de; Lima, Geraldo Μ. de; Pinheiro, Carlos B.; Gil, Rosane A. S. San; Takahashi, Jacqueline A.; Menezes, Daniele C.; Ardisson, José D.

doi:10.1016/j.molstruc.2015.03.044

Cited by 13 publications

(6 citation statements)

References 43 publications

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“…Upon complexation, we have observed the following 119 Sn Mössbauer parameters: δ = 1.29 mm s −1 and Δ = 3.48 mm s −1 ( 1 ); δ = 1.44 mm s −1 and Δ = 3.57 mm s −1 ( 2 ); and δ = 1.28 mm s −1 and Δ = 3.44 mm s −1 ( 3 ). These values for 3 resemble those measured for R 3 Sn valproate complexes . In effect, [Ph 3 Sn(valproate)] constitutes a mononuclear coordination entity with five‐coordinate tin, whereas product 3 is polymeric, as confirmed by single‐crystal X‐ray diffraction (see Section 3.4).…”

Section: Resultssupporting

confidence: 67%

“…These values for 3 resemble those measured for R 3 Sn valproate complexes . In effect, [Ph 3 Sn(valproate)] constitutes a mononuclear coordination entity with five‐coordinate tin, whereas product 3 is polymeric, as confirmed by single‐crystal X‐ray diffraction (see Section 3.4). The decrease of Sn(IV) s‐character upon coordination of 4‐phenylbutyrate relative to that of R 3 SnCl is reflected in the decrease of the isomer shift δ values.…”

Section: Resultssupporting

confidence: 67%

“…These vibration modes are normally observed as strong bands in the FT‐IR spectra of organotin(IV) carboxylates . The Δ ν (COO) = ( ν as − ν s ) value constitutes a spectroscopic means to determine whether the Sn–carboxyl coordination is bidentate or bridging: Δ ν (COO) < 200 cm −1 ; or monodentate: Δ ν (COO) > 200 cm −1 . For the free Na(OPh b ) salt, ν as COO = 1575 cm −1 and ν s COO = 1414 cm −1 , affording Δ ν (COO) = 161 cm −1 .…”

Section: Resultsmentioning

confidence: 99%

“…In a recent paper we have described the X‐ray crystallographic structure of [Ph 3 Sn(valproate)] . This organotin(IV) carboxylate is mononuclear and its Sn(IV) cation lies at the centre of a distorted trigonal bipyramid .…”

Section: Resultsmentioning

confidence: 99%

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Spectroscopic and X‐ray structural characterization of new polymeric organotin(IV) carboxylates and their in vitro antifungal activities: Part II

Rocha

Morais

Rodrigues

et al. 2016

Applied Organom Chemis

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Funding informationCNPq, CAPES and FAPEMIG The reactions of R 3 SnCl (R = Me, Bu or Ph) with sodium 4-phenylbutyrate, Na(OPh b ), in EtOH yielded three polymeric triorganotin carboxylates, namely [R 3 Sn(OPh b )] n (R = Me (1), Bu (2) or Ph (3)). All complexes were spectroscopically characterized using Fourier transform infrared, 119 Sn Mössbauer, 1 H NMR, 13 C{ 1 H} NMR and 119 Sn{ 1 H} NMR spectral techniques. In addition, the crystal structures of 1 and 3 were determined using single-crystal X-ray diffraction. Their polymeric structures are sustained by bridging carboxylates which connect two five-coordinate Sn(IV) centres. Each metallic cation displays a distorted trigonal bipyramidal coordination geometry (Addison's parameters ranging from 0.84 in 1 to 0.77-0.91 in 3), with the oxygen atoms occupying the apical positions and the organic groups at the equatorial corners. The one-dimensional zigzag chains of 1 propagate along the b-axis, whereas 3 displays wave-like double polymeric chains along the b-axis. For both 1 and 3, parallel one-dimensional polymeric chains are interconnected by C─H⋅⋅⋅π interactions. The antifungal activity of 1-3 was screened against Candida albicans (ATCC 18804), C. tropicalis (ATCC 750), C. glabrata (ATCC 90030), C. parapsilosis (ATCC 22019), C. lusitaniae (CBS 6936) and C. dubliniensis (clinical isolate 28). The antifungal activity of 3 was noteworthy since it was not only more active than 1 and 2, but also more active than the control drugs (nystatin and fluconazole nitrate) in some cases.

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Section: Resultssupporting

confidence: 67%

Section: Resultssupporting

confidence: 67%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Spectroscopic and X‐ray structural characterization of new polymeric organotin(IV) carboxylates and their in vitro antifungal activities: Part II

Rocha

Morais

Rodrigues

et al. 2016

Applied Organom Chemis

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“…Organotin(IV) complexes have diverse structural motifs depending on the number and nature of ligands and show numerous biological properties including insecticidal, anti‐tuberculosis, anti‐proliferative, anti‐diabetic, anti‐fungal and anti‐bacterial . In case of macrocyclic organotin(IV) complexes, fluorescent and good anti‐tumor properties are also observed.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization and DFT Study of Bioactive 2‐[(2‐Methylpropanoyl)amino]propanoic Acid and Its Polymeric Tributyltin(IV) Derivative

et al. 2019

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Tributyltin(IV) derivative (1) was synthesized by reacting the ligand (A1) {2‐[(2‐methylpropanoyl)amino]propanoic acid} with tributyltin(IV)chloride in presence of potassium hydroxide. The compounds were characterized by elemental analysis, FTIR and multinuclear (1H, 13C and 119Sn) NMR spectroscopy. The 119Sn NMR data for (1) suggest that tin is five coordinated having trigonal bipyramidal molecular geometry. Molecular structures for (1) and (A1) were determined by single crystal X‐ray analysis. Some new and novel structural features of the compounds, are reported first time. Tributyltin(IV) complex has distorted trigonal bipyramidal molecular geometry around tin in the solid state exhibiting single chain tetramer which may be ascribed as tetra‐nuclear cage structure that is constructed from four tributyltin units and four ligand moieties. The tributyltin(IV) entities are bridged by one oxygen of the carboxylic group of one ligand and another oxygen of the amidic carbonyl of next ligand. The nature of Sn…O bond was analyzed with the help of natural bond orbital (NBO) analysis. The compounds were also screened in vitro for their anti‐microbial and urease inhibition activities, and found some encouraging results.

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Tin and organotin coordination polymers and covalently bonded supramolecular materials – The last 15 years of research

Santos

Lima

2020

Coordination Chemistry Reviews

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Multinuclear NMR and crystallographic studies of triorganotin valproates and their in vitro antifungal activities

Cited by 13 publications

References 43 publications

Spectroscopic and X‐ray structural characterization of new polymeric organotin(IV) carboxylates and their in vitro antifungal activities: Part II

Spectroscopic and X‐ray structural characterization of new polymeric organotin(IV) carboxylates and their in vitro antifungal activities: Part II

Synthesis, Characterization and DFT Study of Bioactive 2‐[(2‐Methylpropanoyl)amino]propanoic Acid and Its Polymeric Tributyltin(IV) Derivative

Tin and organotin coordination polymers and covalently bonded supramolecular materials – The last 15 years of research

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