Anion, cation and ion-pair recognition by bis-urea based receptors containing a polyether bridge

Jancarlo Gómez-Vega; Ramón Alfonso Moreno-Corral; Hisila Santacruz Ortega; David Octavio Corona-Martínez; Herbert Höpfl; Rogerio R. Sotelo-Mundo; Adrián Ochoa-Terán; Raymundo Enrique Escobar-Picos; José Zeferino Ramírez-Ramírez; Octavio Juárez-Sánchez; Karen Ochoa Lara

doi:10.1080/10610278.2019.1578884

Anion, cation and ion-pair recognition by bis-urea based receptors containing a polyether bridge

Jancarlo Gómez-Vega, Ramón Alfonso Moreno-Corral, Hisila Santacruz Ortega, David Octavio Corona-Martínez, Herbert Höpfl, Rogerio R. Sotelo-Mundo, Adrián Ochoa-Terán, Raymundo Enrique Escobar-Picos, José Zeferino Ramírez-Ramírez, Octavio Juárez-Sánchez, Karen Ochoa Lara^*

^*Corresponding author for this work

Research output: Contribution to journal › Article › peer-review

6 Scopus citations

Abstract

Two bis-urea type receptors were synthesized containing a polyether bridge and two 4-nitrophenyl groups as chromogenic units, R1 and R2. Molecular recognition studies of receptors towards different tetraalkylammonium and alkali metal salts were carried out in DMSO by UV-Vis and ¹ H-NMR spectroscopy. The receptors were found to have high affinity for diverse anions and ion-pairs, showing the highest affinities towards the tetramethylammonium and sodium salts. The cation binding ability of the receptors was evidenced by means ¹ H NMR, mass spectrometric ESI ⁺ studies and the crystal structures of some precursors. Additionally, the molecular modelling at the DFT level of the tetramethylammonium acetate complexes illustrates the potential ion-pair binding ability of the receptors: the anion is recognized through strong hydrogen bonds from the NH─ groups from the two urea sites, while the cation is bound by a combination of cation─π, C-H···O and C-H···π interactions.

Original language	English
Pages (from-to)	322-335
Number of pages	14
Journal	Supramolecular Chemistry
Volume	31
Issue number	5
DOIs	https://doi.org/10.1080/10610278.2019.1578884
State	Published - 4 May 2019

Bibliographical note

Funding Information:
This work was supported by the Consejo Nacional de Ciencia y Tecnología [CB-239581,Red Temática de Química Supramolecular 281251,Sabbatical grant 121614].

Funding Information:
This work was supported by the “Consejo Nacional de Ciencia y Tecnología (CONACyT)” under a graduate Grant (for PJGV and REEP), under a sabbatical Grant (number 121614), under Grants CB-239581 and 281251 (“Red Temática de Química Supramolecular”) and under an equipment grant INFR-2014-01-225455 (for the single crystal X-ray diffractometer). Finally, access to the X-ray facilities of the Chemical Research Center at Morelos State University (LANEM) is gratefully acknowledged.

Publisher Copyright:
© 2019, © 2019 Informa UK Limited, trading as Taylor & Francis Group.

Keywords

anion recognition
heteroditopic receptor
ion-pair recognition
polyether bridge
Urea

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10.1080/10610278.2019.1578884

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Gómez-Vega, J., Moreno-Corral, R. A., Santacruz Ortega, H., Corona-Martínez, D. O., Höpfl, H., Sotelo-Mundo, R. R., Ochoa-Terán, A., Escobar-Picos, R. E., Ramírez-Ramírez, J. Z., Juárez-Sánchez, O., & Lara, K. O. (2019). Anion, cation and ion-pair recognition by bis-urea based receptors containing a polyether bridge. Supramolecular Chemistry, 31(5), 322-335. https://doi.org/10.1080/10610278.2019.1578884

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abstract = " Two bis-urea type receptors were synthesized containing a polyether bridge and two 4-nitrophenyl groups as chromogenic units, R1 and R2. Molecular recognition studies of receptors towards different tetraalkylammonium and alkali metal salts were carried out in DMSO by UV-Vis and 1 H-NMR spectroscopy. The receptors were found to have high affinity for diverse anions and ion-pairs, showing the highest affinities towards the tetramethylammonium and sodium salts. The cation binding ability of the receptors was evidenced by means 1 H NMR, mass spectrometric ESI + studies and the crystal structures of some precursors. Additionally, the molecular modelling at the DFT level of the tetramethylammonium acetate complexes illustrates the potential ion-pair binding ability of the receptors: the anion is recognized through strong hydrogen bonds from the NH─ groups from the two urea sites, while the cation is bound by a combination of cation─π, C-H···O and C-H···π interactions. ",

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Gómez-Vega, J, Moreno-Corral, RA , Santacruz Ortega, H, Corona-Martínez, DO, Höpfl, H, Sotelo-Mundo, RR, Ochoa-Terán, A, Escobar-Picos, RE, Ramírez-Ramírez, JZ, Juárez-Sánchez, O & Lara, KO 2019, 'Anion, cation and ion-pair recognition by bis-urea based receptors containing a polyether bridge', Supramolecular Chemistry, vol. 31, no. 5, pp. 322-335. https://doi.org/10.1080/10610278.2019.1578884

TY - JOUR

T1 - Anion, cation and ion-pair recognition by bis-urea based receptors containing a polyether bridge

AU - Gómez-Vega, Jancarlo

AU - Moreno-Corral, Ramón Alfonso

AU - Santacruz Ortega, Hisila

AU - Corona-Martínez, David Octavio

AU - Höpfl, Herbert

AU - Sotelo-Mundo, Rogerio R.

AU - Ochoa-Terán, Adrián

AU - Escobar-Picos, Raymundo Enrique

AU - Ramírez-Ramírez, José Zeferino

AU - Juárez-Sánchez, Octavio

AU - Lara, Karen Ochoa

PY - 2019/5/4

Y1 - 2019/5/4

N2 - Two bis-urea type receptors were synthesized containing a polyether bridge and two 4-nitrophenyl groups as chromogenic units, R1 and R2. Molecular recognition studies of receptors towards different tetraalkylammonium and alkali metal salts were carried out in DMSO by UV-Vis and 1 H-NMR spectroscopy. The receptors were found to have high affinity for diverse anions and ion-pairs, showing the highest affinities towards the tetramethylammonium and sodium salts. The cation binding ability of the receptors was evidenced by means 1 H NMR, mass spectrometric ESI + studies and the crystal structures of some precursors. Additionally, the molecular modelling at the DFT level of the tetramethylammonium acetate complexes illustrates the potential ion-pair binding ability of the receptors: the anion is recognized through strong hydrogen bonds from the NH─ groups from the two urea sites, while the cation is bound by a combination of cation─π, C-H···O and C-H···π interactions.

AB - Two bis-urea type receptors were synthesized containing a polyether bridge and two 4-nitrophenyl groups as chromogenic units, R1 and R2. Molecular recognition studies of receptors towards different tetraalkylammonium and alkali metal salts were carried out in DMSO by UV-Vis and 1 H-NMR spectroscopy. The receptors were found to have high affinity for diverse anions and ion-pairs, showing the highest affinities towards the tetramethylammonium and sodium salts. The cation binding ability of the receptors was evidenced by means 1 H NMR, mass spectrometric ESI + studies and the crystal structures of some precursors. Additionally, the molecular modelling at the DFT level of the tetramethylammonium acetate complexes illustrates the potential ion-pair binding ability of the receptors: the anion is recognized through strong hydrogen bonds from the NH─ groups from the two urea sites, while the cation is bound by a combination of cation─π, C-H···O and C-H···π interactions.

KW - anion recognition

KW - heteroditopic receptor

KW - ion-pair recognition

KW - polyether bridge

KW - Urea

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DO - 10.1080/10610278.2019.1578884

M3 - Artículo

AN - SCOPUS:85062447914

VL - 31

SP - 322

EP - 335

JO - Supramolecular Chemistry

JF - Supramolecular Chemistry

SN - 1061-0278

IS - 5

ER -

Anion, cation and ion-pair recognition by bis-urea based receptors containing a polyether bridge

Abstract

Bibliographical note

Keywords

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