Experimental comparative study of solvent effects on the structure of two sulfonated resorcinarenes

Sanabria, Edilma; Esteso, Miguel A.; Vargas, Édgar F.; Maldonado, Mauricio

doi:10.1016/j.molliq.2018.01.111

Cited by 14 publications

(8 citation statements)

References 29 publications

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“…Despite the importance of this type of molecules, in terms of their applications, there is only one method reported for their separation, which includes successive crystallizations [32]. Continuing with our studies related to structure and applications of resorcinarenes [33–36], in the present investigation, we show an efficient method for the analysis of this kind of stereoisomers by RP-HPLC and it is shown that the mixture can be separated by means of the RP-SPE technique with good yields.…”

Section: Introductionmentioning

confidence: 67%

Analysis by RP-HPLC and Purification by RP-SPE of the C-Tetra(p-hydroxyphenyl)resorcinolarene Crown and Chair Stereoisomers

Castillo-Aguirre

Rivera‐Monroy

Maldonado

2019

Journal of Analytical Methods in Chemistry

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A method for the separation of stereoisomer mixture of the octol C-tetra(p-hydroxyphenyl)calix[4]resorcinarene that was obtained by an acid cyclocondensation reaction between resorcinol and benzaldehyde is reported in this paper. A crude product from octol formation reaction was analyzed by reverse-phase high-performance liquid chromatography (RP-HPLC), and two well-resolved signals corresponding to the crown and chair isomers were found. A reverse phase in solid-phase extraction (RP-SPE) protocol allowed the separation of the two stereoisomers with high purity of each isomer. Finally, the crude and purified stereoisomers were characterized by using FT-IR, 1H-NMR, and 13C-NMR techniques, confirming the chemical identity of the two isomers and the efficiency in the separation process.

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Section: Introductionmentioning

confidence: 67%

Analysis by RP-HPLC and Purification by RP-SPE of the C-Tetra(p-hydroxyphenyl)resorcinolarene Crown and Chair Stereoisomers

Castillo-Aguirre

Rivera‐Monroy

Maldonado

2019

Journal of Analytical Methods in Chemistry

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“…Polyhydroxylated platforms such as calixarenes, resorcinarenes, or pyrogalloarenes (Figure 1) are a very interesting class of compounds. They have a remarkable ability to act as receptors for a variety of guest species, depending on their structural properties [23,24,25,26,27], which can be modified by changing the size of the substituents or by adding functional groups as a part of the scaffold [28,29,30,31,32]. Among the described macrocyclic compounds, calixarenes are probably the most promising for application in the area of host–guest recognition of toxicological molecules.…”

Section: Calix[n]arenesmentioning

confidence: 99%

Calixarenes: Generalities and Their Role in Improving the Solubility, Biocompatibility, Stability, Bioavailability, Detection, and Transport of Biomolecules

2019

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The properties and characteristics of calix[n]arenes are described, as well as their capacity to form amphiphilic assemblies by means of the design of synthetic macrocycles with a hydrophilic head and a hydrophobic tail. Their interaction with various substances of interest in pharmacy, engineering, and medicine is also described. In particular, the role of the calix[n]arenes in the detection of dopamine, the design of vesicles and liposomes employed in the manufacture of systems of controlled release drugs used in the treatment of cancer, and their role in improving the solubility of testosterone and anthelmintic drugs and the biocompatibility of biomaterials useful for the manufacture of synthetic organs is emphasized. The versatility of these macrocycles, able to vary in size, shape, functional groups, and hydrophobicity and to recognize various biomolecules and molecules with biological activity without causing cytotoxicity is highlighted.

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“…As a follow-up to our studies on the reactivity of polihydroxylated macrocyclics [ 21 , 22 , 23 , 24 ] and in order to establish what happens with the crown conformer, in the present study we show the reaction between C- tetra(phenyl)pyrogallol[4]arene (fixed in crown or chair conformation) and acetic anhydride; in pyridine to generate polyacetyl-tetra(phenyl)pyrogallol[4]arene. The products were analyzed using 1 H and 13 C-NMR and FTIR spectroscopy, elemental analysis, mass spectrometry, and dynamic 1 H-NMR spectroscopy.…”

Section: Introductionmentioning

confidence: 82%

Conformational Aspects of the O-acetylation of C-tetra(phenyl)calixpyrogallol[4]arene

Casas-Hinestroza

Maldonado

2018

Molecules

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Reaction between pyrogallol and benzaldehyde results in a conformational mixture of C-tetra(phenyl)pyrogallol[4]arene (crown and chair). The conformer mixture was separated using crystallization procedures and the structures were determined using FTIR, 1H-NMR, and 13C-NMR. O-acetylation of C-tetra(phenyl)pyrogallol[4]arene (chair) with acetic anhydride, in pyridine results in the formation of dodecaacetyl-tetra(phenyl)pyrogallol[4]arene. The structure was determined using 1H-NMR and 13C-NMR finding that the product maintains the conformation of the starting conformer. On the other hand, the O-acetylation reaction of C-tetra(phenyl)pirogallol[4]arene (crown) under same conditions proceeded efficiently, and its structure was determined using 1H-NMR and 13C-NMR. Dynamic 1H-NMR of acetylated pyrogallolarene was studied by means of variable temperature in DMSO-d6 solution, and it revealed that two conformers are formed in the solution. Boat conformations for acetylated pyrogallolarene showed a slow interconversion at room temperature.

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Experimental comparative study of solvent effects on the structure of two sulfonated resorcinarenes

Cited by 14 publications

References 29 publications

Analysis by RP-HPLC and Purification by RP-SPE of the C-Tetra(p-hydroxyphenyl)resorcinolarene Crown and Chair Stereoisomers

Analysis by RP-HPLC and Purification by RP-SPE of the C-Tetra(p-hydroxyphenyl)resorcinolarene Crown and Chair Stereoisomers

Calixarenes: Generalities and Their Role in Improving the Solubility, Biocompatibility, Stability, Bioavailability, Detection, and Transport of Biomolecules

Conformational Aspects of the O-acetylation of C-tetra(phenyl)calixpyrogallol[4]arene

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