2,4-Dioxo-4-phenylbutanoic acid (1). Yield: 7.90 g, 80 %; pale yellow powder; m.p.: C, dcc** (from AcOEt/benzene); C10H8O4, FW: 192.
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1 J. Serb. Chem. Soc. 82 (3) S158 S187 (2017) Supplementary material SUPPLEMENTARY MATERIAL TO Redox properties of alkyl-substituted 4-aryl-2,4-dioxobutanoic acids ILIJA N. CVIJETIĆ1, TATJANA Ž. VERBIĆ2*, BRANKO J. DRAKULIĆ 3**, DALIBOR M. STANKOVIĆ1,4, IVAN O. JURANIĆ3, DRAGAN D. MANOJLOVIĆ2 and MIRE ZLOH5 1Innovation Center of the Faculty of Chemistry, University of Belgrade, Studentski Trg 16, Belgrade, Serbia, 2Faculty of Chemistry, University of Belgrade, Studentski Trg 16, Belgrade, Serbia, 3Institute of Chemistry, Technology and Metallurgy, Department of Chemistry, University of Belgrade, Njegoševa 12, Belgrade, Serbia, 4Vinča Institute of Nuclear Sciences, University of Belgrade, P. O. Box 522, Belgrade, Serbia and 5Department of Pharmacy, University of Hertfordshire, Hatfield, Hertfordshire AL10 9AB, United Kingdom J. Serb. Chem. Soc. 82 (3) (2017) ,4-Dioxo-4-phenylbutanoic acid (1). Yield: 7.90 g, 80 %; pale yellow powder; m.p.: C, dcc** (from AcOEt/benzene); C10H8O4, FW: ; IR (ATR, cm 1): 2997 br (COO H st), 1720 (C=O st), 1626 (C=O st***), 1275 (C O st); 1H-NMR (200 MHz, DMSO-d6, δ / ppm): (1H, s, COOH), 8.00 (2H, d, J = 8.4 Hz, o-h), 7.65 (1H, t, J = 7.3 Hz, p-h), 7.51 (2H, t, J = 7.3 Hz, m-h), 7.32 (1H, s, probably from CH of the less abundant enol form), 7.08 (1H, s, CH of the enol form), 4.57 (1H, bs, CH2 of the diketo from); 13C-NMR (50 MHz, DMSO-d6, δ / ppm): , , , , , , , , , , 98.21, Two tautomeric forms were visible in DMSO solution, and the signal at ppm corresponds to the methylene group of the diketo tautomer. 4-(2-Methylphenyl)-2,4-dioxobutanoic acid (2). Yield: 1.25 g, 76 %; white solid; m.p.: C, dcc (from EtOH); C11H10O4, FW: ; IR (ATR, cm 1): 2991 br (COO H st), 1710 (C=O st), 1635 (C=O st), 1279 (C O st); 1H-NMR (200 MHz, DMSO-d6, δ / ppm): 7.68 (1H, d, J = 8.4 Hz, o-h), 7.48 (1H, t, J = 7.3 Hz, m-h), 7.35 (1H, t, p-h), overlapped with 7.31 (1H, d, J = Hz, m-h), 6.71 (1H, s, CH of enol form), 4.48 (bs, CH2 of diketo form), 2.45 (3H, s, CH3); 13C-NMR (50 MHz, DMSO-d, δ / ppm): , , , , 6 * Corresponding author. tatjanad@chem.bg.ac.rs **Decomposition; *** stretching S158
2 SUPPLEMENTARY MATERIAL S , , , , , , 51.78, 20.62; ESI-HR/MS: Calcd. for C11H9O4 (M H): Found: (3-Methylphenyl)-2,4-dioxobutanoic acid (3). Yield: 0.82 g, 73 %; white solid; m.p.: C (from EtOH), C11H10O4, FW: ; IR (ATR, cm 1): 3501 br (COO H st), 1683 (C=O st), 1628 (C=O st), 1257 (C O st); 1H-NMR (200 MHz, DMSO-d6, δ / ppm): 7.84 (1H, s, o-h), 7.80 (1H, d, J = 8.0 Hz, o-h), 7.45 (1H, d, J = 8.0 Hz, p-h), 7.41 (1H, t, J = 8.0 Hz, m-h), 7.06 (1H, s, CH of enol form), 4.53 (bs, CH2 of diketo form), 2.36 (3H, s, CH3); 13C-NMR (50 MHz, DMSO-d6, δ / ppm): , , , , , , , , , 97.95, 53.13, 20.84; ESI-HR/MS: Calcd. for C11H9O4 (M H): Found: (4-Methylphenyl)-2,4-dioxobutanoic acid (4). Yield: 6.30 g, 61 %; light yellow crystals; m.p.: C (from AcOEt/PhMe); C11H10O4, FW: ; IR (ATR, cm 1): 3520 br (COO H st), 1603 (C=O st), 1248 (C O st); 1H-NMR (500 MHz, CD3OD, δ / ppm): 7.93 (2H, d, J = 8.2 Hz, 2 o-h), 7.85 (less abundant tautomer, d, J = 8.2 Hz), 7.35 (2H, d, J = 8.0 Hz, 2 m-h), 7.30 (less abundant tautomer, d, J = 8.0 Hz), 7.09 (1H, s, CH of enol form), 2.41 (3H, s, CH3); 13C-NMR (125 MHz, CD OD, δ / ppm): , , , , , , , 98.77, (2,4-Dimethylphenyl)-2,4-dioxobutanoic acid (5). Yield: 5.21 g, 78 %; pale yellow solid; m.p.: C (from AcOEt/PhMe); C12H12O4, FW: ; IR (ATR, cm 1): 2969 br (COO H st), 1710 (C=O st), 1633 (C=O st), 1271 (C O st); 1H-NMR (200 MHz, CDCl3, δ / ppm): 7.60 (1H, d, J = 8.4 Hz, o-h), (2H, m, overlapped d and s from 2 m-h), 6.96 (1H, s, CH of enol form), 2.55 (3H, s, CH3), 2.38 (3H, s, CH3); 13C-NMR (50 MHz, CDCl3, δ / ppm): , , , , , , , , , , 21.59; ESI-HR/MS: Calcd. for C12H11O4 (M H): Found: (2,5-Dimethylphenyl)-2,4-dioxobutanoic acid (6). Yield: 7.93 g, 72 %; white powder; m.p.: C (from AcOEt/PhMe); C12H12O4, FW: ; IR (ATR, cm 1): 2969 br (COO H st), 1701 (C=O st), 1619 (C=O st), 1292 (C O st); 1H-NMR (200 MHz, DMSO-d6, δ / ppm): 7.76 (1H, s, o-h), 7.71 (1H, d, J = 8.1 Hz, p-h), 7.28 (1H, d, J = 7.9 Hz, m-h), 6.65 (1H, bs, CH of enol form), 4.40 (bs, CH2 of diketo form), 2.29 (6H, s, 2 CH3); 13C-NMR (50 MHz, DMSO-d6, δ / ppm): , , , , , , 97.88, 19.61, (3,4-Dimethylphenyl)-2,4-dioxobutanoic acid (7). Yield: 6.30 g, 57 %; white powder; m.p.: C, dcc (from AcOEt/PhMe); C12H12O4, FW: ; IR (ATR, cm 1): 3474 br (COO H st), 1705 (C=O st), 1612 (C=O st), 1261 (C O st); 1H-NMR (200 MHz, DMSO-d6, δ / ppm): 7.78 (1H, s, o-h), 7.73 (1H, d, J = 8.1 Hz, o-h), 7.29 (1H, d, J = 7.9 Hz, m-h), 6.77 (1H, bs, CH of enol
3 S160 CVIJETIĆ et al. form), 4.43 (bs, CH2 of diketo from), 2.29 (6H, s, 2 CH3); 13C-NMR (50 MHz, DMSO-d6, δ / ppm): , , , , , , , 97.73, 19.65, ,4-Dioxo-4-(2,4,5-trimethylphenylbutanoic acid (8). Yield: 4.58 g, 68 %; pale yellow solid; m.p.: C (from AcOEt/PhMe); C13H14O4, FW: ; IR (ATR, cm 1): 2925 br (COO H st), 1709 (C=O st), 1619 (C=O st), 1275 (C O st); 1H-NMR (200 MHz, DMSO-d6, δ / ppm): 7.52 (1H, s, o-h), 7.10 (1H, s, m-h), 6.80 (1H, s, CH of enol form), 4.47 (bs, CH2 of diketo form), 2.43 (3H, s, CH3), 2.24 (6H, s, 2 CH3); 13C-NMR (50 MHz, DMSO-d6, δ / ppm): , , , , , , , , , , 51.46, 20.52, 19.35, Two tautomeric forms are visible in DMSO solution, and the signal at ppm corresponds to the methylene group of the diketo tautomer; ESI-HR/MS: Calcd. for C13H13O4 (M H): Found: ,4-Dioxo-4-(2,3,5,6-tetramethylphenylbutanoic acid (9). Yield: 5.20 g, 78 %; white solid; m.p.: C dcc, (from AcOEt/PhMe); C14H16O4, FW: ; IR (ATR, cm 1): 2962 br (COO H st), 1743 (C=O st), 1599 (C=O st), 1261 (C O st); 1H-NMR (200 MHz, DMSO-d6, δ / ppm): 6.96 (1H, s, p-h), 6.21 (1H, s, CH of enol form), 2.13 (6H, s, 2 CH3), 2.04 (6H, s, 2 CH3); 13C-NMR (50 MHz, DMSO-d6, δ / ppm): , , , , , , , , 19.29, 15.98; ESI-HR/MS: Calcd. for C14H15O4 (M H): Found:
4 SUPPLEMENTARY MATERIAL S161 Fig. S-1. Chromatogram for the assessment of the purity of compound 1, with tables showing the detector response at three wavelengths.
5 S162 CVIJETIĆ et al. Fig. S-2. Chromatogram for the assessment of the purity of compound 2, with tables showing the detector response at three wavelengths.
6 SUPPLEMENTARY MATERIAL S163 Fig. S-3. Chromatogram for the assessment of the purity of compound 3, with tables showing the detector response at three wavelengths.
7 S164 CVIJETIĆ et al. Fig. S-4. Chromatogram for the assessment of the purity of compound 4, with tables showing the detector response at three wavelengths.
8 SUPPLEMENTARY MATERIAL S165 Fig. S-5. Chromatogram for the assessment of the purity of compound 5, with tables showing the detector response at three wavelengths.
9 S166 CVIJETIĆ et al. Fig. S-6. Chromatogram for the assessment of the purity of compound 6, with tables showing the detector response at three wavelengths.
10 SUPPLEMENTARY MATERIAL S167 Fig. S-7. Chromatogram for the assessment of the purity of compound 7, with tables showing the detector response at three wavelengths.
11 S168 CVIJETIĆ et al. Fig. S-8. Chromatogram for the assessment of the purity of compound 8, with tables showing the detector response at three wavelengths.
12 SUPPLEMENTARY MATERIAL S169 Fig. S-9. Chromatogram for the assessment of the purity of compound 9, with tables showing the detector response at three wavelengths.
13 S170 CVIJETIĆ et al. Fig. S-10. Absorption spectra of compound 2 used for Ka1 determination in solutions of different acidity, the ph values are indicated; b) Spectrophotometric determination of Ka1 according to Eq. (1); c2 = M; λ = nm; t = 25 C, I = 0.1 M (NaCl); scan speed 500 nm min-1.
14 SUPPLEMENTARY MATERIAL S171 Fig. S-11.Absorption spectra of compound 2 used for Ka2 determination in solutions of different acidity, the ph values are indicated; b) Spectrophotometric determination of Ka2 according to Eq. (2); c2 = M; λ = nm; t = 25 C, I = 0.1 M (NaCl); scan speed 500 nm min-1.
15 S172 CVIJETIĆ et al. Fig. S-12. Absorption spectra of compound 3 used for Ka1 determination in solutions of different acidity, the ph values are indicated; b) Spectrophotometric determination of Ka1 according to Eq. (1); c3 = M; λ = nm; t = 25 C, I = 0.1 M (NaCl); scan speed 500 nm min-1.
16 SUPPLEMENTARY MATERIAL S173 Fig. S-13. Absorption spectra of compound 3 used for Ka2 determination in solutions of different acidity, the ph values are indicated; b) Spectrophotometric determination of Ka2 according to Eq. (2); c3 = M; λ = nm; t = 25 C, I = 0.1 M (NaCl); scan speed 500 nm min-1.
17 S174 CVIJETIĆ et al. Fig. S-14. Absorption spectra of compound 5 used for Ka1 determination in solutions of different acidity, the ph values are indicated; b) Spectrophotometric determination of Ka1 according to Eq (1); c5 = M; λ = nm; t = 25 C, I = 0.1 M (NaCl); scan speed 500 nm min-1.
18 SUPPLEMENTARY MATERIAL S175 Fig. S-15. Absorption spectra of compound 5 used for Ka2 determination in solutions of different acidity, the ph values are indicated; b) Spectrophotometric determination of Ka2 according to Eq. (2); c5 = M; λ = nm; t = 25 C, I = 0.1 M (NaCl); scan speed 500 nm min-1.
19 S176 CVIJETIĆ et al. Fig. S-16. Absorption spectra of compound 6 used for Ka1 determination in solutions of different acidity, the ph values are indicated; b) Spectrophotometric determination of Ka1 according to Eq (1); c6 = M; λ = nm; t = 25 C, I = 0.1 M (NaCl); scan speed 500 nm min-1.
20 SUPPLEMENTARY MATERIAL S177 Fig. S-17. Absorption spectra of compound 6 used for Ka2 determination in solutions of different acidity, the ph values are indicated; b) Spectrophotometric determination of Ka2 according to Eq, (2); c6 = M; λ = nm; t = 25 C, I = 0.1 M (NaCl); scan speed 500 nm min-1.
21 S178 CVIJETIĆ et al. Fig. S-18. Absorption spectra of compound 8 used for Ka1 determination in solutions of different acidity, the ph values are indicated; b) Spectrophotometric determination of Ka1 according to Eq. (1); c8 = М; λ = nm; t = 25 C, I = 0.1 M (NaCl); scan speed 500 nm min-1.
22 SUPPLEMENTARY MATERIAL S179 Fig. S-19. Absorption spectra of compound 8 used for Ka2 determination in solutions of different acidity, the ph values are indicated; b) Spectrophotometric determination of Ka2 according to Eq. (2); c8 = М; λ = nm; t = 25 C, I = 0.1 M (NaCl); scan speed 500 nm min-1.
23 S180 CVIJETIĆ et al. Fig. S-20. Absorption spectra of compound 9 used for Ka1 determination in solutions of different acidity, the ph values are indicated; b) Spectrophotometric determination of Ka1 according to Eq. (1); c9 = M; λ = nm; t = 25 C, I = 0.1 M (NaCl); scan speed 500 nm min-1.
24 SUPPLEMENTARY MATERIAL S181 Fig. S-21. Absorption spectra of compound 9 used for Ka2 determination in solutions of different acidity, the ph values are indicated; b) Spectrophotometric determination of Ka2 according to Eq. (2); c9 = M; λ = nm; t = 25 C, I = 0.1 M (NaCl); scan speed 500 nm min-1.
25 S182 CVIJETIĆ et al. EMP2 (1) = a.u. EMP2 (2) = a.u. EMP2 (3) = a.u. EMP2 (4) = a.u. EMP2 (5) = a.u. EMP2 (6) = a.u. EMP2 (7) = a.u. EMP2 (8) = a.u. EMP2 (9) = a.u. Fig. S-22. Optimized geometries and energies of 1 9 in their molecular (H2A) form; MP2/631g (d,p) with PCM water solvation. EMP EMP2 (1) = a.u. (2) = a.u. EMP2 (3) = a.u. EMP2 (4) = a.u. EMP2 (5) = a.u. EMP2 (6) = a.u. EMP2 (7) = a.u. EMP2 (8) = a.u. EMP2 (9) = a.u. 2 Fig. S-23. Optimized geometries and energies of 1 9 in their monoanionic (HA-) form; MP2/6-31g (d,p) with PCM water solvation.
26 SUPPLEMENTARY MATERIAL S183 Fig. S-24. Cyclic voltammograms of compounds 1 3 and 5 9 in Britton Robinson buffer at ph 1, ph 5, and ph 10. a) 1, c1 = M; b) 2, c2 = M; c) 3, c3 = M; d) 5, c5 = M; e) 6, c6 = M; f) 7, c7 = M; g) 8, c8 = M; h) 9, c9 = M; scan rate 100 mv s-1, t=25±1 C.
27 S184 CVIJETIĆ et al. Fig. S-25. Differential pulse polarograms of compound 2 9 in Britton Robinson buffer at ph 1, ph 5, and ph 10; a) 2, c2 = M; b) 3, c3 = M; c) 4, c4 = M; d) 5, c5 = M; e) 6, c6 = M; f) 7, c7 = M; g) 8, c8 = M; h) 9, c9 = M; scan rate 13 mv s-1, t =25±1 C.
28 S185 SUPPLEMENTARY MATERIAL Compound 4 Compound 6 Compound 9 Fig. S-26. HOMO orbitals of the H2A form of compounds 4, 6 and 9 plotted on the isocontour level Compound 4 Compound 6 Compound 9 Fig. S-27. LUMO orbitals of the H2A form of compounds 4, 6 and 9 plotted on the isocontour level TABLE S-I. Energies of the FMOs (given in Hartree), and dipoles (given in Debye) for the molecular and monoanionic forms of compounds 1 9 Compound HOMO Neutral (H2A) LUMO HOMO/ LUMO gap Dipole HOMO Anion (HA-) LUMO HOMO/ LUMO gap Dipole
29 S186 CVIJETIĆ et al. Table S-II. Energies of the FMOs (given in Hartree), and dipole moments (given in Debye) for the radical anions and radical cations derived from molecular form (H2A) or monoanionic form (HA-) of compounds 1 9. Energies of αsomo and αlumo are shown. Radical anion from H2A SOMO LUMO SOMO/ Dipole LUMO gap Radical dianion from HASOMO/ Compound SOMO LUMO LUMO Dipole gap Compound Radical cation from H2A SOMO LUMO SOMO/ Dipole LUMO gap Table S-III. Intercorrelation matrix (r values) between oxidation/reduction potentials at ph 1 and at ph 5 and the descriptors extracted from QM calculations. The indicator variable (I) is also included. molecular refers to the neutral form of the compounds; anion refers to the anionic form of the compounds (deprotonated carboxyl group); RA refers to the radical anion/dianion (derived from the neutral/anionic form); RC refers to the radical cation derived from the neutral form Eox - ph_1 HOMO (molecular) LUMO (molecular) HOMO/LUMO gap (molecular) Dipole (molecular) SOMO (RC) LUMO (RC) SOMO/LUMO gap (RC) Dipole (RC) I Ered - ph_1 HOMO (molecular) LUMO molecular HOMO/LUMO gap (molecular) Dipole (molecular) SOMO (RA) LUMO (RA) SOMO/LUMO gap (RA) Dipole (RA) I
30 SUPPLEMENTARY MATERIAL S187 Table S-III. Continued Eox - ph_5 HOMO (molecular) LUMO (molecular) HOMO/LUMO gap (molecular) Dipole (molecular) SOMO (RC) LUMO (RC) SOMO/LUMO gap (RC) Dipole (RC) I Ered - ph_5 HOMO (anion) LUMO (anion) HOMO/LUMO gap (anion) Dipole (molecular) SOMO dianion (RA) LUMO dianion (RA) SOMO/LUMO gap dianion (RA) Dipole of dianion (RA) I
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