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1 Supporting Information Redox Reactivity of a Mononuclear Manganese-Oxo Complex Binding Calcium Ion and Other Redox-Inactive Metal Ions Muniyandi Sankaralingam, Yong-Min Lee, Yuliana Pineda-Galvan, Deepika G. Karmalkar, Mi Sook Seo, So Hyun Jeon, Yulia N. Pushkar,*, Shunichi Fukuzumi, *,, and Wonwoo Nam *, Department of Chemistry and Nano Science, Ewha Womans University, Seoul 03760, Korea Department of Physics and Astronomy, Purdue University, 525 Northwestern Ave., West Lafayette, Indiana 47907, USA Faculty of Science and Engineering, SENTAN, Japan Science and Technology Agency (JST), Meijo University, Nagoya, Aichi , Japan wwnam@ewha.ac.kr, fukuzumi@chem.eng.osaka-u.ac.jp, ypushkar@purdue.edu Supporting Information S1
2 Table of Contents Table S1 Table S2 Table S3 Table S4 Table S5 Figure S1 Figure S2 Figure S3 Figure S4 Figure S5 Figure S6 Figure S7 Figure S8 Figure S9 Figure S10 Figure S11 Figure S12 Figure S13 Figure S14 Figure S15 Figure S16 Figure S17 Figure S18 Figure S19 Figure S20 Figure S21 Figure S22 DFT Calculations Cartesian Coordinates S3 S4 S5 S6 S7 S8 S9 S10 S11 S12 S13 S14 S15 S16 S17 S18 S19 S20 S21 S22 S23 S24 S25 S26 S27 S28 S29 S30 S32 Supporting Information S2
3 Table S1. Structural Parameters from EXAFS Fits a for the [Mn III (OH)(dpaq)] + Complex Fit # Shell R, Å N* 2 x 10 3 R-factor Reduced Chi 2 1 Mn-N Mn-O Mn-N * 2.8* Mn-O Mn-N Mn-C * 3.3* Mn-O Mn-N Mn-N Mn-C * 2.3* 2.3* Mn-O Mn-N Mn-N Mn-C Mn-C * 1.9* 1.9* 12* 12* a Fits were done in q-space. R is the Mn backscatter distance. 2 is Debye Waller factor. R- factor and Reduced Chi 2 are the goodness-of-fit parameters (see XAS/EXAFS Section in the text). So 2 =1.0 was used in all fits. * denotes when 2 was set to be the same for multiple vectors in the same coordination shell. Supporting Information S3
4 Table S2. Structural Parameters from EXAFS Fits a for the 1-Sc 3+ Intermediate Fit # Shell R, Å N* 2 x 10 3 R-factor Reduced Chi 2 1 Mn-N Mn-N Mn-C Mn-O Mn-N Mn-C * 5.9* Mn-O Mn-N Mn-C Mn-C * 5.9* 9.4* 9.4* Mn-O Mn-N Mn-C Mn-C Mn-Sc * 6.9* 10.9* 10.9* a Fits were done in q-space. R is the Mn backscatter distance. 2 is Debye Waller factor. R- factor and Reduced Chi 2 are the goodness-of-fit parameters (see XAS/EXAFS Section in the text). So 2 =1.0 was used in all fits. * denotes when 2 was set to be the same for multiple vectors in the same coordination shell. Supporting Information S4
5 Table S3. Structural Parameters from EXAFS Fits a for the 1-Lu 3+ Intermediate Fit # Shell R, Å N* 2 x 10 3 R-factor Reduced Chi 2 1 Mn-N Mn-N Mn-C Mn-O Mn-N Mn-C * 6.2* Mn-O Mn-N Mn-C Mn-C * 6.2* 11.4* 11.4* Mn-O Mn-N Mn-C Mn-C Mn-Lu * 6.7* 11.9* 11.9* a Fits were done in q-space. R is the Mn backscatter distance. 2 is Debye Waller factor. R- factor and Reduced Chi 2 are the goodness-of-fit parameters (see XAS/EXAFS Section in the text). So 2 =1.0 was used in all fits. * denotes when 2 was set to be the same for multiple vectors in the same coordination shell. Supporting Information S5
6 Table S4. One-Electron Oxidation Potentials (Eox) of Electron Donors and Second-Order Rate Constants (ket) of Electron Transfer from Electron Donors to 1-Sc 3+ with Driving Force of Electron Transfer ( ΔGet) in MeCN at 253 K electron donor Eox, V vs SCE ket, M 1 s 1 ΔGet, ev [Fe II (Me2bpy)3] [Fe II (bpy)3] [Fe II (phen)3] [Ru II (Me2bpy)3] Supporting Information S6
7 Table S5. One-Electron Oxidation Potentials (Eox), Electrophilic Substitution Constants ( p + ) of para-x-substituted Thioanisoles, and Second-Order Rate Constants (kox) of Oxidation of para-x-substituted Thioanisoles by 1-Sc 3+ in MeCN at 253 K with Driving Force of Electron Transfer ( ΔGet) para-x Eox a, V vs SCE σp + b kox, M 1 s 1 ΔGet, ev OMe Me H Cl Br a Taken from the reference: Goto, Y.; Matsu, T.; Ozaki, S.; Watanabe, Y.; Fukuzumi, S. J. Am. Chem. Soc. 1999, 121, b Taken from the reference: Hammett, L. P. J. Am. Chem. Soc. 1937, 59, 96. Supporting Information S7
8 Figure S1. X-ray crystal structure of [(dpaq)mn III (OH)](OTf) showing 50% probability ellipsoids. Trifluoromethanesulfonate ion and hydrogen atoms are omitted for clarity. The parameters are the same as previously reported one (see ref 30a in the text: Wijeratne, G. B.; Corzine, B.; Day, V. W.; Jackson, T. A. Inorg. Chem. 2014, 53, 7622). Supporting Information S8
9 Figure S2. 1 H-NMR spectra of the [(dpaq)mn III (OH)](OTf) complex in the (a) absence and (b) presence of D2O (25 μl) in CD3CN (500 μl) at 298 K. The observed spectra were identical to the previously reported ones (see ref 30b in the text: Rice, D. B.; Jones, S. D.; Douglas, J. T.; Jackson, T. A. Inorg. Chem. 2018, 57, Supporting Information S9
10 Figure S3. EPR spectra (first derivative, integrated, and doubly integrated spectra from the bottom to the top) of (a) 2,2-diphenyl-1-picrylhydrazyl radical (DPPH, 0.50 mm) as a reference and (b) bis(μ-oxo)dimanganese(iii,iv) complex, [(dpaq)mn III (μ-o)2mn IV (dpaq)] + (0.50 mm), which was produced in the reaction of [(dpaq)mn III (OH)] + (1.0 mm) with PhIO (1.5 mm) in MeCN at 263 K. Spectra were recorded on a JEOL X-band spectrometer (JES- FA100) to determine the spin amount of [(dpaq)mn III (μ-o)2mn IV (dpaq)] + at 77 K. Supporting Information S10
11 Figure S4. X-band CW-EPR spectra of 1-M n+ (2.0 mm) [(a) 1-Ca 2+, (b) 1-Mg 2+, (c) 1-Zn 2+, (d) 1-Lu 3+, (e) 1-Y 3+, (f) 1-Al 3+, and (g) 1-Sc 3+ ]. All spectra were recorded in MeCN at 5 K except for the spectrum of 1-Ca 2+, which was recorded at 77 K. The peaks at g = ~2 with hyperfine splitting in (a) (e) are due to the presence of [(dpaq)mn III (μ-o)2mn IV (dpaq)] + as an impurity (< 3%). Supporting Information S11
12 Figure S5. Experimental (black line) and simulated (red line) X-band CW-EPR spectra of (a) 1-Mg 2+ and (b) 1-Lu 3+. Simulation parameters for 1-Mg 2+ : S = 3/2, microwave frequency = GHz, g = [2.05, 2.05, 1.93], A( 55 Mn) = 93 G, D = 1 cm 1, E/D = 0, Gaussian linewidth (FWHM) = 600 G. Simulation parameters for 1-Lu 3+ : S = 3/2, microwave frequency = GHz, g = [2.70, 1.88, 1.80], A( 55 Mn) = 93 G, D = 1 cm 1, E/D = 0, Hstrain = [0, 3000, 1000] MHz, Gaussian linewidth (FWHM) = 50 G. Supporting Information S12
13 Figure S6. Overlay of the Fourier Transform of 1-Sc 3+ (k = Å 1 ) and the result of fit #5 in Table S2. Supporting Information S13
14 Figure S7. X-band CW-EPR spectra of (a) [(dpaq)mn III (μ-o)2mn IV (dpaq)] + and (b) 1-Ca 2+. Spectra were recorded at 77 K. (c) Modified EPR spectrum obtained by subtracting the EPR spectrum of 1-Ca 2+ by 2.9% of EPR spectrum of the [(dpaq)mn III (μ-o)2mn IV (dpaq)] +, indicating the impurity of the dimer species is less than 3%. Supporting Information S14
15 Figure S8. CSI-MS spectra of (a) 1-Zn 2+, (b) 1-Lu 3+, and (c) 1-Y 3+ in MeCN at 253 K. The peaks at m/z = 815.1, , and correspond to [(dpaq)mn IV (O)] + -Zn(OTf)2 (calc. m/z = 815.1), [(dpaq)mn IV (O)] + -Lu(OTf)3 (calc. m/z = ), and [(dpaq)mn IV (O)] + -Y(OTf)3 (calc. m/z = 988.9), respectively. Supporting Information S15
16 Figure S9. Normalized Mn K-edge XANES of [(dpaq)mn III (OH)] + (black line), 1-Sc 3+ (red line), 1-Lu 3+ (green line), and 1-Zn 2+ (violet line). Supporting Information S16
17 Figure S10. Overlay of the Fourier Transform of 1-Lu 3+ (k = Å -1 ) and the result of fit #5 in Table S3. Supporting Information S17
18 Figure S11. (a) U-vis spectral changes for the reaction of bis(μ-oxo)dimanganese(iii,iv) complex with the substrates, such as (a) thioanisole (100 mm), (b) 1,4-CHD (100 mm), and (c) Fe II (Me2bpy)3] 2+ (5.0 mm) in MeCN at 253 K. The inset shows the time profiles monitored at 520 nm for thioanisole and 1,4-CHD and 620 nm for Fe II (Me2bpy)3] 2+ due to bis(μ-oxo)dimanganese(iii,iv) complex. Supporting Information S18
19 Figure S12. Plots of the pseudo-first-order rate constants (k1) vs concentrations of oneelectron donors [(a) [Fe II (Me2bpy)3] 2+, (b) [Fe II (bpy)3] 2+, (c) [Fe II (phen)3] 2+, and (d) [Ru II (Me2bpy)3] 2+ ] to determine the second-order rate constants (ket) for the electron transfer reactions from one-electron donors to 1-Sc 3+ in MeCN at 253 K. Supporting Information S19
20 Figure S13. Plots of the pseudo-first-order rate constants against the concentrations of [Fe II (Me2bpy)3] 2+ to determine the second-order rate constants (ket) for the electron transfer reactions from [Fe II (Me2bpy)3] 2+ to (a) 1-Ca 2+, (b) 1-Mg 2+, (c) 1-Zn 2+, (d) 1-Lu 3+, (e) 1-Y 3+, and (f) 1-Al 3+ in MeCN at 253 K. Supporting Information S20
21 Figure S14. Plots of the pseudo-first-order rate constants against concentrations of parasubstituted thioanisoles [(a) p-meo-thioanisole, (b) p-me-thioanisole, (c) p-cl-thioanisole, and (d) p-br-thioanisole] to determine the second-order rate constants (kox) for the oxidation of thioanisole derivatives by 1-Sc 3+ in MeCN at 253 K. Supporting Information S21
22 Figure S15. Plots of log kox against (a) Eox and (b) σp + of para-substituted thioanisoles (para- X-C6H4SCH3; X = MeO, Me, H, Cl, and Br) for the oxidation of para-substituted thioanisoles by 1-Sc 3+ in MeCN at 253 K. Supporting Information S22
23 Figure S16. (a) ESI-MS spectrum of the complete reaction solution obtained in the oxidation of thioanisole by 1-Sc 3+ in MeCN at 253 K. Peak at m/z = corresponds to [(dpaq)mn III (OH)(CH3CN)2] + (calc. m/z = 536.1). (b) EPR spectrum of the complete reaction solution obtained in the reaction of 1-Sc 3+ with thioanisole in MeCN at 253 K. EPR spectrum was recorded at 5 K. Supporting Information S23
24 Figure S17. GC-MS spectra of (a) methyl phenyl sulfoxide as an authentic reference and (b) methyl phenyl sulfoxide product obtained in the oxidation of thioanisole by 18 O-labeled 1- Sc 3+ in MeCN at 253 K. The percentage of 18 O incorporation in the methyl phenyl sulfoxide product was determined to be 80(4)% by comparison of the relative abundances at m/z = 142 for methyl phenyl sulfoxide- 18 O and at m/z = 140 for methyl phenyl sulfoxide- 16 O. Supporting Information S24
25 Figure S18. Plots of the pseudo-first-order rate constants against thioanisole concentrations to determine the second-order rate constants (kox) for the oxidation of thioanisole by (a) 1- Ca 2+, (b) 1-Mg 2+, (c) 1-Zn 2+, (d) 1-Lu 3+, (e) 1-Y 3+, and (f) 1-Al 3+ in MeCN at 253 K. Supporting Information S25
26 Figure S19. (a) Visible-NIR absorption spectral change in the reaction of 1-Sc 3+ (0.25 mm) with DHA (25.0 mm) in deaerated MeCN at 253 K. Inset shows time profile of absorbance at 700 nm. (b) Plot of log kox' of 1-Sc 3+ against C-H BDE of substrates. Second-order rate constants (kox) were determined at 253 K and then adjusted for reaction stoichiometry to yield kox' based on the equivalent target C-H bonds of substrates (e.g., 2 for xanthene, 4 for DHA, and CHD). Supporting Information S26
27 Figure S20. (a) ESI-MS spectrum of the complete reaction solution obtained in the oxidation of xanthene by 1-Sc 3+ in MeCN at 253 K. Peaks at m/z = 585.9, 536.0, and correspond to [(dpaq)mn III (OTf)] + (calc. m/z = 586.0), [(dpaq)mn III (OH)(CH3CN)2] + (calc. m/z = 536.1), and [(dpaq)mn III (OH)] + (calc. m/z = 454.1), respectively. (b) EPR spectrum of the complete reaction solution obtained in the oxidation of DHA by 1-Sc 3+ in MeCN at 253 K. EPR spectrum was recorded at 5 K. Supporting Information S27
28 Figure S21. GC-MS spectra of (a) xanthone as an authentic reference and (b) xanthone product obtained in the oxidation of xanthene by 18 O-labeled 1-Sc 3+ in MeCN at 253 K. The percentage of 18 O incorporation in the xanthone product was determined to be 80(4)% by comparison of the relative abundances at m/z = 198 for xanthone- 18 O and at m/z = 196 for xanthone- 16 O. Supporting Information S28
29 Figure S22. (a) UV-vis spectral changes for the formation of AcrCO Al 3+ complex produced in the reaction of 10-methylacridone (AcrCO, mm; black line) with Al(OTf)3 (0.30 mm; red line) in deaerated MeCN at 298 K. (b) Fluorescence spectra of AcrCO (black line) and AcrCO Al 3+ complex (red line) in deaerated MeCN at 298 K. The excitation wavelength was 430 nm for both the AcrCO and AcrCO Al 3+ complex, and the emission and excitation slit widths were 2.0 nm. Supporting Information S29
30 DFT Calculations. All density functional theory (DFT) 1 calculations were carried out using the Gaussian 09 package 2 with the B3LYP functional. 3 Geometry optimizations and frequency analysis were done using a double-ζ LACVP basis set 4 for all atoms except S atom, which required G*. Single-point calculations on the optimized structures were performed at the B3LYP/LACV3P+* level to obtain more accurate energies. Energy of the high spin state S = 3/2 was 6.49 kcal mol -1 lower than that of the low spin state S = 1/2 with the LACVP basis set. References (1) Kohn, W.; Sham, L. Self-Consistent Equations Including Exchange and Correlation Effects. J. Phys. Rev. 1965, 140, A1133. (2) Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci, B.; Petersson, G. A.; Nakatsuji, H; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov, A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.; Vreven, T.; Montgomery, J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J. J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.; Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.; Rega, N.; Millam, J. M.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.; Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth, G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.; Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian 09, Revision B.01, Gaussian Inc.: Wallingford CT, (3) (a) Becke, A. D. Density-Functional Exchange-Energy Approximation with Correct Asymptotic Behavior, Phys. Rev. A 1988, 38, (b) Becke, A. D. A New Mixing of Hartree Fock and Local Density Functional Theories. J. Chem. Phys. 1993, 98, (c) Becke, A. D. Density Functional Thermochemistry. III. The Role of Exact Exchange. J. Chem. Phys. 1993, 98, (d) Lee, C.; Yang, W.; Parr, R. G. Development of the Supporting Information S30
31 Colle-Salvetti Correlation-Energy Formula into a Functional of the Electron Density. Phys. Rev. B 1988, 37, 785. (4) (a) The LACVP and LACV3P*+ basis sets uses pople style 6-31G and G* basis sets (respectively) on all atoms except transition metals, where an ECP is used as defined in the quantum chemistry program Jaguar, version 7.7, Schrödinger, LLC, NewYork, NY, See also (b) Hay, P. J.; Wadt, W. R. Ab initio Effective Core Potentials for Molecular Calculations. Potentials for K to Au Including the Outermost Core Orbitals. J. Chem. Phys. 1985, 82, 299. (c) Dyall, K. G. Relativistic Double-Zeta, Triple-Zeta, and Quadruple-Zeta Basis Sets for the 5d Elements Hf Hg. Theor. Chem. Acc. 2004, 112, 403. Supporting Information S31
32 Cartesian Coordinates 4 [(dpaq)mn IV (O)(Sc(OTf) 3] + Mn O O N N N N N C H C H C H C C H C H C H C C C C H H C H H C C H C H C H C H C H H C C H C H C H C H O S C F O Sc O S C F O O S O O C F O O F F F F F F Supporting Information S32
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