Host-guest inclusion systems of tetra(alkyl)resorcin [4]arenes with choline in DMSO: Dynamic NMR studies and X-ray structural characterization of the 1:1 inclusion complex

Velásquez-Silva, Astrid; Forero, Roger Sarmiento; Sanabria, Edilma; Pérez‐Redondo, Adrián; Maldonado, Mauricio

doi:10.1016/j.molstruc.2019.07.093

Cited by 10 publications

(4 citation statements)

References 34 publications

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“…These results suggest a low interaction of these resorcinarenes with L-carnitine. Despite the fact that the resorcinarenes on their upper rim are structurally equivalent, the effect of the interaction of the alkyl chains on the lower rim affects the cavity size, this effect being greater with long-chain resorcinarenes, as has previously been observed in other studies [45,46].…”

Section: Molecular Interaction Studies Between Resorcinarenes and L-c...supporting

confidence: 55%

Evaluation of a Resorcinarene-Based Sorbent as a Solid-Phase Extraction Material for the Enrichment of L-Carnitine from Aqueous Solutions

Ramirez,

Cadavid-Montoya,

Maldonado

2023

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We present five new sorbents for the evaluation of the pre-concentration of L-carnitine. The sorbents were obtained from copolymerization between butylmethacrylate (BuMA) and ethylene dimethacrylate (EDMA), which were physically modified on their surface by each one of the five synthetized resorcinarenes of variable chain length studied, with long-chain resorcinarenes exhibiting better fixation on the copolymer. The characterization of the synthesized resorcinarenes was done using FTIR-ATR, 1H NMR, 13C NMR, and mass spectrometry, while characterization of the sorbents was done using FTIR-ATR and scanning electron micrography (SEM). The molecular interaction between L-carnitine and the synthesized resorcinarenes was studied in DMSO via 1H-NMR spectroscopy and, in the gas phase, via electrospray ionization-mass spectrometry (ESI-MS). The results showed that the short-chain resorcinarenes underwent a stable interaction with the neurotransmitter. Once the sorption of resorcinarenes on the copolymer was accomplished, the best parameters for the evaluation of the L-carnitine preconcentration were established. The solution tests were carried out through LC/MS analysis, obtaining better results for L-carnitine absorption with the short-chain resorcinarenes such as tetra(ethyl)calix[4]resorcinarene and tetra(propyl)calix[4]resorcinarene.

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Section: Molecular Interaction Studies Between Resorcinarenes and L-c...supporting

confidence: 55%

Evaluation of a Resorcinarene-Based Sorbent as a Solid-Phase Extraction Material for the Enrichment of L-Carnitine from Aqueous Solutions

Ramirez,

Cadavid-Montoya,

Maldonado

2023

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“…Similarly, the 13 C-NMR signals for NCH2 were found at δ =52.13-49.58 ppm and δ =46.87-41.35 ppm [14,19]. The peaks at δ =32.67-21.66 ppm were attributed to the methylene carbons of the long alkyl chains, while the peak at the chemical shift δ =15.96-14.58 ppm could be assigned to the terminal methyl carbon of the alkyl chains [20].…”

Section: Resultsmentioning

confidence: 99%

New Schiff base compounds with benzene moiety: FT-IR, 1H and 13C NMR Spectroscopy (1D) studies

Khalefa

2020

basjs

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New Schiff bases compounds containing benzene moiety has been synthesized from reaction between (4-(((4-(Alkyloxy) benzylidene) amino) methyl) phenyl)methan amine and 4-((6-bromohexyl) oxy)benzaldehyde or 4-(4-bromobutoxy)benzaldehyde. FT-IR of these compounds have been studied. The complete 1H and 13C NMR assignment of these compounds has been obtained using one-dimensional NMR techniques including 1H and 13C experiments. The data deduced from this study show that the alkyl chain and the phenyl rings are in different planes compared to the benzene ring.

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“…It is interesting to note that the use of calix[4]resorcinarenes as macrocyclic molecules for ion or molecule recognition can contribute significantly in this field of toxic metals removal. Calix[4]resorcinarenes, commonly known as resorcinarenes, are obtained from the condensation reaction of resorcinol with different aldehydes in acid solutions [ 12 , 13 ], and they can be modified with various substituents on their upper rim in order to provide specific functionality and selectivity [ 14 , 15 , 16 ]. Calix[4]resorcinarenes have been widely used in numerous applications, such as sensors [ 17 , 18 ], catalysis [ 19 ], dendrimer synthesis [ 20 , 21 ], dyeing of fibers [ 22 , 23 ], NMR solvating agents [ 24 , 25 ], heavy metal complexes for water purification [ 26 , 27 ], and chemical separations by modification of multiple surface types [ 28 , 29 ].…”

Section: Introductionmentioning

confidence: 99%

Removal of Toxic Metal Ions Using Poly(BuMA–co–EDMA) Modified with C-Tetra(nonyl)calix[4]resorcinarene

Castillo-Aguirre

Maldonado

Esteso

2022

Toxics

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A copolymer of poly(BuMA–co–EDMA) modified with C-tetra(nonyl)calix[4]resorcinarene was obtained via the impregnation method. The formation of the modified copolymer was confirmed and investigated using various techniques; in this way, the presence of calix[4]resorcinarene was confirmed by FT-IR spectroscopy and by high resolution transmission electron microscopy. The modified copolymer was used for the removal of highly toxic cations (Pb2+, Hg2+, and Cd2+) from aqueous solutions. To perform the removal, we used the batch sorption technique and the effects of time of contact, pH, and volume of sample on the effective sorption were determined. The best results were observed for Pb2+ extraction, which was comparatively more efficient. Adsorption–desorption experiments revealed that the modified copolymer could be used for several cycles without significant loss of adsorption capacity. Finally, the results showed that the modified copolymer application is highly efficient for the removal of lead ions from aqueous solutions.

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Host-guest inclusion systems of tetra(alkyl)resorcin [4]arenes with choline in DMSO: Dynamic NMR studies and X-ray structural characterization of the 1:1 inclusion complex

Cited by 10 publications

References 34 publications

Evaluation of a Resorcinarene-Based Sorbent as a Solid-Phase Extraction Material for the Enrichment of L-Carnitine from Aqueous Solutions

Evaluation of a Resorcinarene-Based Sorbent as a Solid-Phase Extraction Material for the Enrichment of L-Carnitine from Aqueous Solutions

New Schiff base compounds with benzene moiety: FT-IR, 1H and 13C NMR Spectroscopy (1D) studies

Removal of Toxic Metal Ions Using Poly(BuMA–co–EDMA) Modified with C-Tetra(nonyl)calix[4]resorcinarene

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