Synthesis and application of chelated complexes [Zn(L-arg)2(H2O)] and [[Zn(L-arg)2(H2O)](SO4)]2– as chiral selectors

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Abstract

By interaction of compounds Zn(II) and L-arginine (L-Arg) the chelated complexes [Zn(L-arg)2(H2O)] (I) and [[Zn(L-arg)2(H2O)](SO4)]2– (II) (L-arg is a deprotonated form of L-Arg) were synthesized. The structure of the obtained complexes was established by IR spectroscopy by comparing the experimental and theoretical IR spectra using quantum chemical modeling. Complexes I and II were studied as chiral selectors of enantioselective voltammetric sensors. It was shown that I exhibits better enantioselective compared to II. By DFT method, it was found that the difference in the exhibited enantioselectivity of complexes I and II can be due of the geometric isomerism of chelate compounds and the peculiarities of the coordination of the obtained complexes with the analyte molecule.

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About the authors

R. R. Gizatov

Ufa University of Science and Technology

Email: berestovatv@gmail.com
Russian Federation, Ufa

Yu. B. Teres

Ufa University of Science and Technology

Email: berestovatv@gmail.com
Russian Federation, Ufa

M. N. Galimov

Ufa University of Science and Technology

Email: berestovatv@gmail.com
Russian Federation, Ufa

E. O. Bulysheva

Ufa University of Science and Technology

Email: berestovatv@gmail.com
Russian Federation, Ufa

T. V. Berestova

Ufa University of Science and Technology

Author for correspondence.
Email: berestovatv@gmail.com
Russian Federation, Ufa

R. A. Zilberg

Ufa University of Science and Technology

Email: berestovatv@gmail.com
Russian Federation, Ufa

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Supplementary files

Supplementary Files
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2. Fig. 1. Energy parameters of trans- and cis-isomers of the [Zn(L-arg)2(H2O)] complex.

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3. Fig. 2. Experimental (red) and theoretical (black) IR spectra of trans- and cis-dimensions of the [Zn(L-arg)2(H2O)] complex in the region of characteristic absorption bands.

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4. Fig. 3. Experimental (blue) and theoretical (black) IR spectra of complexes IIa (a) and IIb (b) in the region of characteristic absorption bands.

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5. Fig. 4. Differential-pulse voltammograms of 1 mM solutions of enantiomers of biologically active substances on different electrodes: (a, b, c) GCE/PEC-trans-[Zn(L-arg)2(H2O)] and (d, d, e) GCE/PEC-cis-[[Zn(L-arg)2(H2O)](SO4)]2− (phosphate buffer solution with pH 6.86, potential scan rate 0.2 V/s).

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6. Fig. 5. Quatovochemical modeling of the intermediates trans-[[Zn(L-arg)2(H2O)](SO4)]2– (a), cis-[[Zn(L-arg)2(H2O)](SO4)]2– (b), trans-[Zn(L-arg)2(H2O)] Tyr (c) and cis-[Zn(L-arg)2(H2O)] Tyr (d).

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7. Fig. 6. Energy parameters of the intermediates trans-[[Zn(L-arg)2(H2O)](SO4)]2– and cis-[[Zn(L-arg)2(H2O)](SO4)]2– (a), trans-[Zn(L-arg)2(H2O)] Tyr and cis-[Zn(L-arg)2(H2O)] Tyr (b).

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8. Scheme 1. Synthesis of complexes [Zn(L-arg)2(H2O)] (I) and [[Zn(L-arg)2(H2O)](SO4)]2– (II).

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