Molecular Recognition of Strong Acids by Using a 2-Ureido-4-Ferrocenyl Pyrimidine Receptor

Soma J. Keszei; Szabolcs Balogh; Csaba Fehér; Lívia Nagy; Nikolay Tumanov; Johan Wouters; Gyorgy Lendvay; Rita Skoda-Földes

doi:10.1002/ejic.201900803

Molecular Recognition of Strong Acids by Using a 2-Ureido-4-Ferrocenyl Pyrimidine Receptor

Soma J. Keszei, Szabolcs Balogh, Csaba Fehér, Lívia Nagy, Nikolay Tumanov, Johan Wouters, Gyorgy Lendvay, Rita Skoda-Földes

Résultats de recherche: Contribution à un journal/une revue › Article › Revue par des pairs

Résumé

The properties of a ferrocenyl ureidopyrimidine derivative, a potential electrochemical sensor for trifluoromethanesulfonic acid and trifluoroacetic acid, were investigated using UV/Vis, NMR and CV measurements. Upon protonation a structural change was found to take place leading to the formation of a proper binding site for the anion of the acid. Anion binding has been proved for both CF3SO3- and CF3CO2-as well as for the BF4- anion by 1H NMR measurements. Moreover, titration experiments carried out with CF3SO3H and CF3CO2H resulted in different responses in the NMR spectra of the pyrimidine host. Cyclic voltammetry was found to be suitable to follow the addition of the acids to the host molecule. DFT calculations and X-ray diffraction were used to explore the properties of anion binding.

langue originale	Anglais
Pages (de - à)	4095-4104
Nombre de pages	10
journal	European Journal of Inorganic Chemistry
Volume	2019
Numéro de publication	38
Les DOIs	https://doi.org/10.1002/ejic.201900803
Etat de la publication	Publié - 17 oct. 2019

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10.1002/ejic.201900803

https://onlinelibrary.wiley.com/doi/abs/10.1002/ejic.201900803

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@article{cd9d179c6b2e417387f3c0acde678397,

title = "Molecular Recognition of Strong Acids by Using a 2-Ureido-4-Ferrocenyl Pyrimidine Receptor",

abstract = "The properties of a ferrocenyl ureidopyrimidine derivative, a potential electrochemical sensor for trifluoromethanesulfonic acid and trifluoroacetic acid, were investigated using UV/Vis, NMR and CV measurements. Upon protonation a structural change was found to take place leading to the formation of a proper binding site for the anion of the acid. Anion binding has been proved for both CF3SO3- and CF3CO2-as well as for the BF4- anion by 1H NMR measurements. Moreover, titration experiments carried out with CF3SO3H and CF3CO2H resulted in different responses in the NMR spectra of the pyrimidine host. Cyclic voltammetry was found to be suitable to follow the addition of the acids to the host molecule. DFT calculations and X-ray diffraction were used to explore the properties of anion binding.",

keywords = "Cyclic voltammetry, DFT calculations, Ferrocene, Hhost-guest systems, NMR spectroscopy",

author = "Keszei, {Soma J.} and Szabolcs Balogh and Csaba Feh{\'e}r and L{\'i}via Nagy and Nikolay Tumanov and Johan Wouters and Gyorgy Lendvay and Rita Skoda-F{\"o}ldes",

note = "Funding Information: This work was supported by the GINOP‐2.3.2‐15‐2016‐00049 grant. L. Nagy acknowledges the support of the National Research, Development and Innovation Office (Budapest, Hungary) under grant K125244. Access to the PC2 technological platform (UNamur) for the X‐ray diffraction measurements is also acknowledged. Funding Information: This work was supported by the GINOP-2.3.2-15-2016-00049 grant. L. Nagy acknowledges the support of the National Research, Development and Innovation Office (Budapest, Hungary) under grant K125244. Access to the PC2 technological platform (UNamur) for the X-ray diffraction measurements is also acknowledged. Publisher Copyright: {\textcopyright} 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim",

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doi = "10.1002/ejic.201900803",

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T1 - Molecular Recognition of Strong Acids by Using a 2-Ureido-4-Ferrocenyl Pyrimidine Receptor

AU - Keszei, Soma J.

AU - Balogh, Szabolcs

AU - Fehér, Csaba

AU - Nagy, Lívia

AU - Tumanov, Nikolay

AU - Wouters, Johan

AU - Lendvay, Gyorgy

AU - Skoda-Földes, Rita

N1 - Funding Information: This work was supported by the GINOP‐2.3.2‐15‐2016‐00049 grant. L. Nagy acknowledges the support of the National Research, Development and Innovation Office (Budapest, Hungary) under grant K125244. Access to the PC2 technological platform (UNamur) for the X‐ray diffraction measurements is also acknowledged. Funding Information: This work was supported by the GINOP-2.3.2-15-2016-00049 grant. L. Nagy acknowledges the support of the National Research, Development and Innovation Office (Budapest, Hungary) under grant K125244. Access to the PC2 technological platform (UNamur) for the X-ray diffraction measurements is also acknowledged. Publisher Copyright: © 2019 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

PY - 2019/10/17

Y1 - 2019/10/17

N2 - The properties of a ferrocenyl ureidopyrimidine derivative, a potential electrochemical sensor for trifluoromethanesulfonic acid and trifluoroacetic acid, were investigated using UV/Vis, NMR and CV measurements. Upon protonation a structural change was found to take place leading to the formation of a proper binding site for the anion of the acid. Anion binding has been proved for both CF3SO3- and CF3CO2-as well as for the BF4- anion by 1H NMR measurements. Moreover, titration experiments carried out with CF3SO3H and CF3CO2H resulted in different responses in the NMR spectra of the pyrimidine host. Cyclic voltammetry was found to be suitable to follow the addition of the acids to the host molecule. DFT calculations and X-ray diffraction were used to explore the properties of anion binding.

AB - The properties of a ferrocenyl ureidopyrimidine derivative, a potential electrochemical sensor for trifluoromethanesulfonic acid and trifluoroacetic acid, were investigated using UV/Vis, NMR and CV measurements. Upon protonation a structural change was found to take place leading to the formation of a proper binding site for the anion of the acid. Anion binding has been proved for both CF3SO3- and CF3CO2-as well as for the BF4- anion by 1H NMR measurements. Moreover, titration experiments carried out with CF3SO3H and CF3CO2H resulted in different responses in the NMR spectra of the pyrimidine host. Cyclic voltammetry was found to be suitable to follow the addition of the acids to the host molecule. DFT calculations and X-ray diffraction were used to explore the properties of anion binding.

KW - Cyclic voltammetry

KW - DFT calculations

KW - Ferrocene

KW - Hhost-guest systems

KW - NMR spectroscopy

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DO - 10.1002/ejic.201900803

M3 - Article

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JO - European Journal of Inorganic Chemistry

JF - European Journal of Inorganic Chemistry

IS - 38

ER -

Molecular Recognition of Strong Acids by Using a 2-Ureido-4-Ferrocenyl Pyrimidine Receptor

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