Spectroscopic Characterization and Antioxidant Properties of Mandelic Acid and Its Derivatives in a Theoretical and Experimental Approach
Abstract
:1. Introduction
1.1. Mandelic Acid and Its Derivatives—Properties and Applications of Studied Compounds
1.2. The Antioxidant Reaction Mechanisms Description
2. Materials and Methods
2.1. Materials
2.2. FTIR and Raman Spectra
2.3. NMR Spectra
2.4. Evaluation of Antioxidant Activity
2.5. Computational Details
- Ropt is the optimal value of a bond length. For C-C type of bonds in a benzene ring, the Ropt value is equal to 1.334;
- Ri is the length of the ith bond;
- n is the number of bond lengths in the ring;
- Rar is the average bond length;
- α is the normalization factor necessary to obtain a HOMA value equal to 1 for ideally aromatic benzene or 0 for an ideally alternating cyclohexatriene Kekulé ring.
3. Results
3.1. The Antioxidant Activity of Mandelic Acid and Its Derivatives
3.2. Computational Results
3.2.1. Structure of Mandelic Acid and Their Derivatives
3.2.2. Bond Dissociation Enthalpy, Ionization Potentials, Proton Dissociation Enthalpies, Proton Affinities and Electron Transfer Enthalpies for Mandelic Acid and Its Derivatives
3.2.3. Aromaticity
3.2.4. HOMO and LUMO Parameters
3.2.5. Electron Charge Distribution and EPS Distribution
3.3. FT-IR and Raman Spectroscopy
NMR Study
- 13C NMR
- 1H NMR
4. Conclusions
Author Contributions
Funding
Institutional Review Board Statement
Informed Consent Statement
Data Availability Statement
Conflicts of Interest
Abbreviations
ABTS | 2,2-azino-bis(3-ethylbenzothiazoline-6-sulfonic acid |
DPPH | 2,2-diphenyl-1-picrylhydrazyl radical |
BDE | bond dissociation energy |
CUPRAC | Cupric ion reducing antioxidant capacity |
DFT | density functional theory |
ETE | electron transfer enthalpy |
FRAP | ferric reducing ability of plasma |
HAT | hydrogen atom transfer |
IP | ionization potential |
MA | Mandelic acid |
PA | proton affinity |
PCET | proton-coupled electron transfer |
SAMMA | mandelic acid condensation polymer |
SPLET | sequential proton loss electron transfer |
3OH-MA | 3-hydroxymandelic acid |
3,4-diOH-MA | 3,4-dihydroxymandelic acid |
4OH-3OCH3-MA | 4-hydroxy-3-methoxymandelic acid |
PDE | proton dissociation enthalpy |
HOMA | harmonic oscillator model of aromaticity |
HOMO | highest Occupied Molecular Orbital |
LUMO | lowest Occupied Molecular Orbital |
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Mandelic Acid | 3-Hydroxymanndelic Acid | 3,4-Dihydroxymandelic Acid | 4-Hydroxy-3-Metoxymandelic Acid | |
---|---|---|---|---|
Energy [hartree] | −535.51 | −610.76 | −685.99 | −725.31 |
Energy [kJ/mol] | −1,406,909.87 | −1,604,604.26 | −1,802,266.09 | −1,905,551.83 |
Dipole moment [De] | 2.41 | 1.92 | 0.27 | 1.47 |
BDE [kcal/mol] | ||||
---|---|---|---|---|
Compound | Vacuum | Water | Ethanol | |
Solvent | ||||
MA | 97.65 | 407.23 | 409.11 | |
3OH-MA | 77.06 | 396.1 | 389.21 | |
3,4-diOH-MA | ||||
3-OH radical | 70.74 | 382.56 | 384.45 | |
4-OH radical | 62.21 | 382.45 | 384.33 | |
4OH-3OCH3-MA | 69.9 | 382.16 | 383.9 | |
IP [kcal/mol] | ||||
MA | 199.33 | 131.92 | 139.63 | |
3OH-MA | 188.75 | 136.01 | 142.10 | |
3,4-diOH-MA | 178.05 | 113.81 | 121.47 | |
4OH-3OCH3-MA | 176.92 | 112.78 | 120.36 | |
PDE [kcal/mol] | ||||
MA | 212.48 | 0.06 | −4.18 | |
3OH-MA | 202.49 | −15.16 | −13.31 | |
3,4-diOH-MA | ||||
3-OH radical | 206.85 | −6.49 | −10.67 | |
4-OH radical | 198.32 | −6.60 | −10.78 | |
4OH-3OCH3-MA | 207.14 | −5.86 | −10.10 | |
PA [kcal/mol] | ||||
MA | 318.21 | 42.12 | 40.92 | |
3OH-MA | 331.68 | 30.38 | 28.85 | |
3,4-diOH-MA | ||||
3-OH radical | 329.34 | 29.84 | 28.28 | |
4-OH radical | 315.39 | 23.25 | 21.30 | |
4OH-3OCH3-MA | 326.11 | 28.64 | 26.99 | |
ETE [kcal/mol] | ||||
MA | 93.60 | 89.86 | 94.55 | |
3OH-MA | 59.55 | 90.47 | 86.71 | |
3,4-diOH-MA | ||||
3-OH radical | 55.56 | 77.47 | 82.53 | |
4-OH radical | 61.01 | 83.96 | 89.39 |
Aromaticity Indice | Solution/Gas Phase | Mandelic Acid | 3-Hydroxy- Mandelic Acid | 3,4-Dihydroxy- Mandelic Acid | 4-Hydroxy-3-Methoxy Mandelic Acid |
---|---|---|---|---|---|
HOMA | Water | 0.989 | 0.988 | 0.980 | 0.986 |
Gas phase | 0.989 | 0.988 | 0.988 | 0.984 | |
Ethanol | 0.984 | 0.989 | 0.980 | 0.980 | |
I6 | Water | 98.90 | 97.74 | 96.57 | 95.84 |
Gas phase | 98.90 | 97.74 | 97.75 | 95.81 | |
Ethanol | 98.53 | 98.65 | 96.53 | 95.84 | |
BAC | Water | 0.984 | 0.959 | 0.940 | 0.930 |
Gas phase | 0.984 | 0.959 | 0.959 | 0.918 | |
Ethanol | 0.975 | 0.980 | 0.939 | 0.930 |
Mandelic Acid | |||||
---|---|---|---|---|---|
Solvent | ΔE [eV] | Hardness [eV] | Softness [eV] | Electrophilicity [eV] | Electronegativity [eV] |
Ethanol | 0.223 | 0.112 | 8.965 | 0.102 | 0.151 |
Water | 0.223 | 0.112 | 8.954 | 0.102 | 0.151 |
Vacuum | 0.218 | 0.109 | 9.154 | 0.050 | 0.149 |
3-hydroxymandelic acid | |||||
Ethanol | 0.203 | 0.102 | 9.830 | 0.097 | 0.140 |
Water | 0.204 | 0.102 | 9.814 | 0.097 | 0.140 |
Vacuum | 0.198 | 0.099 | 10.120 | 0.097 | 0.139 |
3,4-dihydroxymandelic acid | |||||
Ethanol | 0.190 | 0.100 | 10.406 | 0.090 | 0.133 |
Water | 0.193 | 0.100 | 10.388 | 0.090 | 0.133 |
Vacuum | 0.191 | 0.100 | 10.449 | 0.090 | 1.132 |
4-hydroxy-3-methoxymandelic acid | |||||
Ethanol | 0.200 | 0.100 | 10.004 | 0.090 | 0.137 |
Water | 0.201 | 0.100 | 9.970 | 0.137 | 0.137 |
Vacuum | 0.200 | 0.100 | 10.016 | 0.090 | 0.136 |
NBO Atom Charge Distribution | |||
---|---|---|---|
Mandelic Acid | |||
Atom * | Ethanol | Water | Vacuum |
C1 | −0.063 | −0.064 | −0.060 |
C2 | −0.196 | −0.198 | −0.192 |
C3 | −0.202 | −0.201 | −0.197 |
C4 | −0.205 | −0.205 | −0.200 |
C5 | 0.201 | −0.202 | −0.194 |
C6 | −0.108 | −0.197 | 0.190 |
C7 | 0.030 | 0.029 | 0.036 |
C8 | 0.810 | 0.810 | 0.799 |
H2 | 0.215 | 0.219 | 0.207 |
H3 | 0.215 | 0.215 | 0.205 |
H4 | 0.214 | 0.215 | 0.205 |
H5 | 0.214 | 0.215 | 0.206 |
H6 | 0.218 | 0.215 | 0.220 |
H7 | 0.212 | 0.212 | 0.201 |
H8 | 0.487 | 0.487 | 0.481 |
H9 | 0.585 | 0.506 | 0.488 |
O1 | −0.750 | −0.751 | −0.729 |
O2 | −0.670 | −0.670 | −0.671 |
O3 | −0.636 | −0.637 | −0.613 |
3-hydroxymandelic acid | |||
C1 | −0.042 | −0.043 | −0.04 |
C2 | −0.273 | −0.273 | −0.273 |
C3 | 0.319 | 0.318 | −0.323 |
C4 | −0.257 | −0.258 | −0.250 |
C5 | −0.181 | −0.182 | −0.176 |
C6 | −0.229 | −0.230 | −0.226 |
C7 | 0.031 | 0.030 | 0.037 |
C8 | 0.810 | 0.810 | 0.800 |
H2 | 0.223 | 0.223 | 0.218 |
H4 | 0.223 | 0.223 | 0.218 |
H5 | 0.216 | 0.216 | 0.206 |
H6 | 0.216 | 0.217 | 0.209 |
H7 | 0.213 | 0.213 | 0.203 |
H8 | 0.487 | 0.488 | 0.481 |
H9 | 0.506 | 0.506 | 0.488 |
H10 | 0.487 | 0.488 | 0.468 |
O1 | −0.758 | −0.751 | −0.732 |
O2 | −0.669 | −0.669 | −0.669 |
O3 | −0.636 | −0.637 | −0.613 |
O5 | −0.692 | −0.692 | −0.672 |
3,4-dihydroxymandelic acid | |||
C1 | −0.073 | −0.074 | −0.081 |
C2 | −0.253 | −0.253 | −0.213 |
C3 | 0.274 | 0.273 | 0.254 |
C4 | 0.271 | 0.271 | 0.283 |
C5 | −0.257 | −0.257 | −0.265 |
C6 | −0.208 | −0.208 | −0.178 |
C7 | 0.032 | 0.031 | 0.039 |
C8 | 0.809 | 0.818 | 0.799 |
H2 | 0.218 | 0.219 | 0.217 |
H5 | 0.219 | 0.220 | 0.284 |
H6 | 0.220 | 0.220 | 0.221 |
H7 | 0.211 | 0.212 | 0.200 |
H8 | 0.486 | 0.497 | 0.481 |
H9 | 0.505 | 0.505 | 0.488 |
H10 | 0.488 | 0.489 | 0.470 |
H11 | 0.488 | 0.489 | 0.466 |
O1 | −0.751 | −0.752 | −0.730 |
O2 | −0.671 | −0.671 | −0.671 |
O3 | −0.638 | −0.639 | −0.613 |
O4 | −0.686 | −0.687 | −0.659 |
O5 | −0.686 | −0.687 | −0.711 |
4-hydroxy-3-methoxymandelic acid | |||
C1 | −0.082 | −0.083 | −0.077 |
C2 | −0.212 | −0.213 | −0.207 |
C3 | 0.264 | 0.263 | 0.273 |
C4 | 0.282 | 0.282 | 0.277 |
C5 | −0.262 | −0.262 | −0.265 |
C6 | −0.190 | −0.190 | −0.187 |
C7 | 0.032 | 0.032 | 0.039 |
C8 | 0.809 | 0.810 | 0.799 |
H2 | 0.223 | 0.224 | 0.219 |
H5 | 0.219 | 0.220 | 0.201 |
H6 | 0.221 | 0.221 | 0.222 |
H7 | 0.211 | 0.212 | 0.200 |
H8 | 0.486 | 0.487 | 0.480 |
H9 | 0.505 | 0.506 | 0.487 |
H10 | 0.188 | 0.188 | 0.183 |
H12 | 0.490 | 0.491 | 0.470 |
H13 | 0.171 | 0.171 | 0.162 |
H14 | 0.180 | 0.179 | 0.182 |
O1 | −0.751 | −0.752 | −0.731 |
O2 | −0.670 | −0.671 | −0.670 |
O3 | −0.638 | −0.639 | −0.515 |
O4 | −0.687 | −0.687 | −0.676 |
O5 | −0.589 | −0.591 | −0.569 |
Mandelic Acid | 3-Hydroxymandelic Acid | 3,4-Dihydroxymandelic Acid | 4-Hydroxy-3-Methoxymandelic acid | Assignment | |||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
IRKBr | IRATR | Raman | Theor. (1) | IRKBr | IRATR | Raman | Theor. | IRKBr | IRATR | Raman | Theor. | IRKBr | IRATR | Raman | Theor. | ||||||
cm−1 (int.) | cm−1 (int.) | cm−1 (int.) | cm−1 | Int. | cm−1 (int.) | cm−1 (int.) | cm−1 (int.) | cm−1 | Int. | cm−1 (int.) | cm−1 (int.) | cm−1 (int.) | cm−1 | Int. | cm−1 (int.) | cm−1 (int.) | cm−1 (int.) | cm−1 | Int. | [45] | |
3420 s | 3408 m | 3427 w | 3850 | 93.8 | 3402 s | 3850 | 93.8 | νOHar | |||||||||||||
3338 s | 3327 m | 3834 | 62.7 | 3335 s | 3330 m | 3792 | 113.0 | νOHar | |||||||||||||
3400 s | 3401 m | 3755 | 86.1 | 3755 | 88.0 | 3756 | 86.1 | 3353 vs | 3329 m | 3756 | 89.4 | νOH | |||||||||
3734 | 109.5 | 3730 | 112.2 | 3732 | 112.3 | 3728 | 78.9 | νOH | |||||||||||||
3070 m | 3074 w | 3064 vs | 3197 | 5.4 | 3062 vw | 3066 vw | 3070 s | 3198 | 5.8 | 3198 w | 3175 w | 3209 | 1.1 | 3087 vw | 3069 vs | 3203 | 1.7 | ν(CH) | 2 | ||
3031 m | 3038 w | 3049 m | 3188 | 16.96 | 3035 w | 3032 vw | 3185 | 9.4 | 3032 w | 3031 s | 3186 | 1.6 | 3034 vw | 3034 s | 3182 | 2.9 | ν(CH) | 20a | |||
2967 m | 2972 m | 3177 | 19.9 | 3173 | 6.3 | 2974 w | 2973 w | 2974 m | ν(CH) | 20b | |||||||||||
2927 m | 2936 w | 3167 | 2.1 | 3170 | 5.2 | 2945 w | 2911 w | 2916 m | 3154 | 14.4 | 2935 w | 2932 w | 2935 s | 3146 | 18.6 | ν(CH) | 7b | ||||
2716 m | 2722 m | 3015 | 17.4 | 2628 m | 2622 w | 3016 | 16.5 | 3017 | 18.1 | 3014 | 38.5 | νCH | |||||||||
1716 vs | 1711 vs | 1719 m | 1797 | 335.6 | 1715 vs | 1713 vs | 1796 | 333.4 | 1708 vs 1695 vs | 1692 vs | 1648 m | 1795 | 336.2 | 1743 vs 1718 s | 1743 s 1715 s | 1716 m | 1796 | 317.3 | νC=O | ||
1603 m | 1642 | 4.2 | 1605 s | 1603 s | 1609 m | 1644 | 31.1 | 1622 m | 1620 w | 1618 s | 1659 | 8.0 | 1611 m | 1610 m | 1609 s | 1647 | 22.7 | ν(CC) | 8a | ||
1588 w | 1588 w | 1627 | 0.4 | 1641 | 86.1 | 1606 s | 1603 m | 1605 s | 1646 | 46.7 | 1634 | 22.9 | ν(CC) | 8b | |||||||
1497 w | 1497 w | 1524 | 10.5 | 1466 vs | 1465 s | 1529 | 12.0 | 1537 s | 1534 m | 1530 vw | 1544 | 183.7 | 1517 vs | 1515 s | 1548 | 225.6 | ν(CC) | 19a | |||
1460 sh | 1460 sh | 1461 m | 1510 | 8.9 | δas(CH3) | ||||||||||||||||
1451 m | 1488 | 6.7 | δas(CH3) | ||||||||||||||||||
1452 m | 1453 m | 1483 | 9.2 | 1485 | 96.8 | 1452 m | 1450 m | 1449 vw | 1491 | 2.2 | 1439 s | 1437 s | 1447 m | 1481 | 6.7 | ν(CC) | 19b | ||||
1378 m | 1377 m | 1423 | 18.3 | 1420 m | 1420 m | 1423 | 19.5 | 1431 s | 1428 s | 1414 vw | 1426 | 18.9 | βOH; δCHOH | ||||||||
1366 | 0.1 | 1368 | 18.8 | 1377 sh | 1389 | 14.8 | 1380 m | 1377 m | 1376 w | ν(CC) | 3 | ||||||||||
1348 | 4.0 | 1359 w | 1348 | 33.1 | 1351 | 85.4 | ν(CC); βCH | 14 | |||||||||||||
1299 s | 1296 s | 1295 w | 1340 | 92.0 | 1268 vs | 1265 s | 1265 w | 1342 | 77.8 | 1350 s | 1347 s | 1355 m | 1341 | 88.8 | 1365 sh | βOH; νC–OH | |||||
1253 w | 1253 vw | 1256 vw | 1307 | 2.5 | 1249 vs | 1245 vs | 1324 | 7.1 | 1283 s | 1280 s | 1293 m | 1319 | 25.0 | 1270 vs | 1267 s | 1265 m | τCHOH(CH2); β(CH) | ||||
1303 | 237.0 | 1305 | 203.3 | νC–OH; α(CCC); νC–CH3 | |||||||||||||||||
1229 m | 1228 m | 1222 vw | 1253 | 27.5 | 1232 sh | 1254 | 37.4 | 1259 s | 1256 s | 1261 w | 1251 | 54.2 | 1237 vs | 1234 s | 1251 | 55.7 | ωCHOH(CH2) | ||||
1192 m | 1192 m | 1192 m | 1207 | 6.4 | 1214 vs | 1208 vs | 1220 s | 1219 vs | 1193 m | β(CH); βOHar | 9a | ||||||||||
1156 vw | 1154 vw | 1155 w | 1195 | 8.7 | 1168 s | 1167 m | 1167 w | 1196 | 47.2 | 1151 s | 1148 s | 1155 m | 1208 | 43.3 | 1150 vs | 1148 vs | 1147 w | 1207 | 27.5 | β(CH); ρ(CH3) | 9b |
1170 | 166.8 | 1179 | 39.5 | 1180 | 75.2 | 1185 | 48.4 | βOH | |||||||||||||
1132 m | 1131 s | 1171 | 5.0 | ρ(CH3) | |||||||||||||||||
1062 s | 1062 s | 1058 vw | 1089 | 79.7 | 1083 s | 1079 vs | 1082 m | 1085 | 66.0 | 1119 s | 1116 s | 1111 m | 1102 | 86.3 | 1061 s | 1057 s | 1061 m | 1101 | 116.1 | β(CH) | 18a |
1028 w | 1030 w | 1030 m | 1048 | 7.1 | 1089 vs | 1084 vs | 1085 w | 1032 s | 1031 s | 1032 m | β(CH) | 18b | |||||||||
1018 | 0.6 | 1013 | 4.8 | 960 | 18.2 | α(CCC) | 13 | ||||||||||||||
954 w | 954 w | 953 w | 1040 | 89.4 | νO–(CH3) | ||||||||||||||||
1004 w | 1004 w | 1004 s | 1118 | 104.8 | 1001 m | 1001 w | 1000 vs | 1118 | 83.1 | 982 m | 980 m | 1124 | 208.4 | α(CCC); νC–OH | 12 | ||||||
940 m | 940 m | 985 | 0.1 | 869 s | 982 | 0.1 | 920 sh | 923 sh | 937 | 1.9 | 924 w | 913 m | 947 | 0.3 | γ(CH) | 17a | |||||
889 m | 887 m | 892 | 22.1 | 932 m | 967 w | 919 | 16.2 | 881 s | 880 s | 908 m | 911 | 23.4 | 880 m | 936 | 12.6 | νC–COOH; α(CCC); γOH | |||||
855 w | 854 w | 858 w | 869 | 2.0 | 826 m | 826 m | 821 w | 860 | 6.6 | 868 m | 867 m | 869 | 8.3 | 863 m | 861 s | 878 | 7.8 | βC=O | |||
816 | 1.7 | 836 | 18.2 | 835 | 20.1 | γC=O; α(CCC) | |||||||||||||||
768 w | 768 w | 768 vw | 763 | 16.7 | 732 s | 731 vs | 725 m | 788 | 28.5 | 835 m | 833 m | 792 | 36.6 | 825 m | 822 s | 824 w | 811 | 28.1 | γ(CH) | 11 | |
733 s | 731 s | 732 w | 727 | 50.9 | 697 s | 695 s | 720 | 54.8 | 807 s | 801 s | 784 vs | 725 | 1.8 | 775 m | 773 s | 777 m | 746 | 1.4 | φ(CC) | 4 | |
697 s | 697 s | 709 | 33.2 | 674 m | 671 s | 695 | 26.7 | 732 m | 731 m | 718 m | 706 | 36.1 | 732 m | 731 m | 707 | 31.8 | α(CCC) | 1 | |||
609 m | 608 m | 617 w | 660 | 35.1 | 637 w | 660 | 39.8 | 646 m | 662 m | 661 | 43.8 | 707 m | 693 s | 701 m | 662 | 27.0 | γC=O; βOH | ||||
528 m | 570 | 52.2 | 505 m | 545 | 20.4 | 603 w | 585 w | 549 | 28.8 | 634 w | 546 | 19.8 | γOH | ||||||||
494 m | 501 w | 498 | 4.1 | 462 m | 475 | 14.4 | 519 m | 475 | 20.3 | 533 w | 471 | 21.8 | φ(CC); γOH | 16b | |||||||
467 w | 413 | 4.4 | 413 | 53.2 | 468 m | 403 | 48.3 | 465 w | 402 | 35.2 | φ(CC); βOH | 16a |
Compound | ||||||||
---|---|---|---|---|---|---|---|---|
Mandelic Acid | 3-OH-Mandelic Acid | 3,4-Dihydoxymandelic Acid | 4-Hydroxy-3-Methoxymandelic Acid | |||||
13C NMR | ||||||||
assignment | Calc. | Exp. | Calc. | Exp. | Calc. | Exp. | Calc. | Exp. |
C1 * | 146.02 | 140.39 | 147.49 | 141.62 | 138.31 | 131.10 | 137.91 | 131.13 |
C2 | 129.71 | 126.85 | 113.89 | 113.47 | 118.61 | 114.14 | 128.73 | 110.80 |
C3 | 133.36 | 128.34 | 163.51 | 157.13 | 150.89 | 144.90 | 153.63 | 146.12 |
C4 | 133.39 | 127.87 | 118.26 | 114.51 | 149.05 | 144.90 | 156.53 | 147.26 |
C5 | 133.15 | 128.34 | 134.76 | 129.00 | 117.19 | 115.06 | 119.51 | 115.01 |
C6 | 133.58 | 126.85 | 124.10 | 117.31 | 120.68 | 117.83 | 125.42 | 119.33 |
C7 | 75.56 | 72.63 | 75.08 | 72.33 | 74.74 | 72.13 | 74.81 | 72.21 |
C8 | 182.50 | 174.36 | 182.60 | 174.04 | 182.56 | 174.48 | 182.73 | 174.39 |
C9 | - | - | - | - | - | - | 60.07 | 55.56 |
1H NMR | ||||||||
H2 | 7.89 | 7.45 | 7.17 | 6.82 | 7.25 | 6.80 | 7.35 | 6.96 |
H3 | 7.69 | 7.35 | -- | - | - | - | - | - |
H4 | 7.62 | 7.34 | 7.23 | 7.11 | - | - | - | - |
H5 | 7.61 | 7.35 | 6.98 | 7.11 | 6.95 | 6.64 | 6.90 | 6.72 |
H6 | 7.75 | 7.45 | 7.47 | 7.13 | 7.25 | 6.65 | 7.45 | 6.95 |
H7 | 3.34 | 5.08 | 3.17 | 4.89 | 3.14 | 4.80 | 3.15 | 4.88 |
H8 | 5.47 | 5.08 | 5.46 | 6.81 | 5.33 | 5.55 | 5.33 | 5.69 |
H9 | 6.60 | 12.69 | 6.05 | 12.41 | 6.55 | 12.38 | 6.51 | 12.44 |
H10 | - | - | 4.57 | 9.36 | 4.54 | 8.90 | - | - |
H11 | - | - | - | - | 5.33 | 8.82 | 4.53 | 8.93 |
H12 | - | - | - | - | - | - | 3.92 | 3.74 |
H13 | - | - | - | - | - | - | 3.44 | 3.74 |
H14 | 3.15 | 3.74 |
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Parcheta, M.; Świsłocka, R.; Świderski, G.; Matejczyk, M.; Lewandowski, W. Spectroscopic Characterization and Antioxidant Properties of Mandelic Acid and Its Derivatives in a Theoretical and Experimental Approach. Materials 2022, 15, 5413. https://doi.org/10.3390/ma15155413
Parcheta M, Świsłocka R, Świderski G, Matejczyk M, Lewandowski W. Spectroscopic Characterization and Antioxidant Properties of Mandelic Acid and Its Derivatives in a Theoretical and Experimental Approach. Materials. 2022; 15(15):5413. https://doi.org/10.3390/ma15155413
Chicago/Turabian StyleParcheta, Monika, Renata Świsłocka, Grzegorz Świderski, Marzena Matejczyk, and Włodzimierz Lewandowski. 2022. "Spectroscopic Characterization and Antioxidant Properties of Mandelic Acid and Its Derivatives in a Theoretical and Experimental Approach" Materials 15, no. 15: 5413. https://doi.org/10.3390/ma15155413