Altmetrics
Downloads
88
Views
27
Comments
0
A peer-reviewed article of this preprint also exists.
supplementary.pdf (1.38MB )
Submitted:
06 November 2023
Posted:
07 November 2023
You are already at the latest version
complexes | Colour | Yield (%) | Melting point (°C) | Solubility |
---|---|---|---|---|
L1 | colorless | 330 | soluble in DMSO | |
Cu(II)L1 | yellow-green | 61 | >350 ᵒC | soluble in DMSO, DMF, C2H5OH, H2O and insoluble in THF, EtOAc and C6H12. |
Pd(II)L1 | brown | 72 | >350 ᵒC | soluble in DMSO, DMF and insoluble in H2O, THF, C2H5OH, EtOAc and C6H12. |
L2 | colorless | 218-220 | soluble in DMSO | |
Cu(II)L2 | yellow-green | 43 | 260-263 ᵒC | soluble in DMSO and insoluble in H2O, THF, C2H5OH, EtOAc and C6H12. |
Pd(II)L2 | brown | 70 | 255-257 ᵒC | soluble in DMSO, DMF and insoluble in H2O, THF, C2H5OH, EtOAc and C6H12. |
assignment | L1 | Cu(II)L1 | Pd(II)L1 |
---|---|---|---|
ν(OH) | - | - | 3442 |
ν(NH) | 3115 sh | 3115 | 3111 |
ν(NH) | 3080 | 3080 | 3071 |
ν(=CH) | 3014 | 3003 | 3052 |
ν(C=O) | 1676 m | 1637 | 1678 |
1560 w | 1559 | 1559 | |
ν(C=S) | 1242 | 1242 | 1244 |
1167 s | 1167 | 1168 |
assignment | L2 | Cu(II)L2 | Pd(II)L2 |
---|---|---|---|
ν(OH) | - | 3451 | 3437 |
ν(NH) | 3112 | - | 3117 |
ν(NH) | 3093 | 3093 | 3080 |
ν(=CH) | 3042 | 3042 | |
ν(C=O) | 1656 | 1651 | 1657 |
1557 | 1553 | 1545 | |
ν(C=S) | 1243 | 1232 | 1261 |
1165 | 1166 | 1175 |
Atom | δ (13C) ppm | DEPT-135 | δ (1H) ppm | Multiplicity (J, Hz) | 1H-1H COSY | HMBC |
---|---|---|---|---|---|---|
1 (NH) | 12.29 | s | ||||
2 (C=S) | 175.87 | C | ||||
3 (NH) | 12.29 | s | ||||
4 (C=O) | 161.06 | C | ||||
5 | 103.72 | CH | 5.68 | d (0.9) | 7 | 4b, 6, 7 |
6 | 153.20 | C | ||||
1’ | 18.11 | CH3 | 2.06 | d (0.7) | 5 | 5, 6 |
Atom | δ (13C) ppm | DEPT -135 | δ (1H) ppm | Multiplicity (J, Hz) | 1H-1H COSY |
---|---|---|---|---|---|
1 (NH) | - | - | 12.20 | s | |
2 (C=S) | 176.08 | C | - | ||
3 (NH) | - | - | 12.31 | s | |
4 (C=O) | 161.22 | C | - | ||
5 | 103.06 | CH | 5.67 | s | |
6 | 156.74 | C | |||
1’ | 33.21 | CH2 | 2.32 | t(7.5) | 2’ |
2’ | 20.58 | CH2 | 1.54 | sx(7.4) | 1’, 3’ |
3‘ | 13.26 | CH3 | 0.87 | t(7.4) | 2’ |
Atom | L1 | L2 | Cu(II)L1 | Cu(II)L2 | Pd(II)L2 |
---|---|---|---|---|---|
1 (NH) | |||||
2 (C=S) | 174.6 | 175.5 | 171.7/174.8 | 168.3/175.4 | 172.3/172.9/174.0 |
3 (NH) | |||||
4 (C=O) | 163.0 | 164.8 | 162.9/169.5 | 164.9/166.1 | 160.3/166.4/167.0 |
5 (CH) | 104.7 | 103.8/104.6 | 104.7/105.4 | 103.8/104.6/105.4/107.2 | 95.8/103.1/105.0 |
6 (C) | 156.2 | 159.9 | 154.0/156.4 | 159.9/161.3 | 153.0/156.0/159.7 |
1´ | 20.2 | 32.7 | 20.1 | 32.7/39.3/39.6/40.9 | 33.4/34.2/38.6 |
2´ | 19.6/20.2 | 18.2/19.7/20.2/24.4 | 18.2/19.3/19.7 | ||
3´ | 13.1/14.7 | 13.1/13.6/14.7/15.7 | 12.9/15.4 | ||
DMSO | 40.3 |
metal complex | composition* | formula | Moleculаr weight | W(M)% calc./exp. |
---|---|---|---|---|
Cu(II)L1 | [3LCu.(DMSO)] | C17H24N6O4S4Cu | M=568.22 g/mol | 11.2 / 11.6±0.6 |
Pd(II)L1 | [5LPd.(DMSO)].H2O | C27H38N10O7S6Pd | M=913.46 g/mol | 11.6 / 11.1±0.6 |
Cu(II)L2 | [LCu.H2O.(OH-)2.(DMSO)2] | C11H26N2O6S3Cu | M=442.07 g/mol | 14.4 / 14.3±0.7 |
Pd(II)L2 | [4LPd.(DMSO)2].H2O | C32H54N8O7S6Pd | M=961.63 g/mol | 11.1 / 11.5±0.5 |
Atom | L1 (6-methyl-2-thiouracil) |
Cu(II)L1 Multiplicity (J, Hz) |
Pd(II)L1 Multiplicity (J, Hz) |
---|---|---|---|
1 (NH) | 12.29 s | 12.24 s | 12.24 s and 10.80 |
2 (C=S) | – | – | – |
3 (NH) | 12.29 s | 12.29 s | 12.30 s and 10.86 |
4 (C=O) | – | – | – |
5 | 5.68 | 5.68 s | 5.68 s and 5.31 |
6 | - | - | - |
1’ | 2.06 | 2.07 | 2.07 and 2.01 |
Atom | δ (13C) ppm, L1 | Cu(II)L1 | Pd(II)L1 |
---|---|---|---|
1 (NH) | – | – | – |
2 (C=S) | 175.87 | 175.86 | 175.86 / ? |
3 (NH) | – | – | – |
4 (C=O) | 161.06 | 161.01 | 161.01 / ? |
5 | 103.72 | 103.69 | 103.69 and 98.71 |
6 | 153.20 | 153.12 | 153.12 / ? |
1’ | 18.11 | 18.06 | 18.06 and 18.20 |
Atom | L2 (6-propyl-2-thiouracil) |
Cu(II)L2 Multiplicity (J, Hz) |
Pd(II)L2 Multiplicity (J, Hz) |
---|---|---|---|
1 (NH) | 12.20 s | 12.20 s | 12.20 and 10.77 s |
2 (C=S) | - | - | - |
3 (NH) | 12.31 s | 12.31 s | 12.32 and 10.87 s |
4 (C=O) | - | - | - |
5 | 5.67 s | 5.67 s | 5.68 and 5.31 s and t(1.8) |
6 | - | - | - |
1’ | 2.32 t(7.5) | 2.32 t(7.4) | 2.32 and 2.25 t(7.3) and t(7.3) |
2’ | 1.54 sx(7.4) | 1.54 sx(7.5) | 1.54 and 1.48 sx(7.6) and m |
3’ | 0.87 t(7.4) | 0.88 t(7.3) | 0.87 and 0.82 t(7.3) and m |
DMSO | - | 2.54 s | 2.54 s |
Atom | δ (13C) ppm, L2 | Cu(II)L2 | Pd(II)L2 |
---|---|---|---|
1 (NH) | - | - | - |
2 (C=S) | 176.08 | 176.02 | |
3 (NH) | - | - | - |
4 (C=O) | 161.22 | 164.19 and 161.09 | |
5 | 103.06 | 98.03 | |
6 | 156.74 | 156.61 and 156.33 and 151.71 | |
1’ | 33.21 | 33.24 | 33.56 and 33.14 |
2’ | 20.58 | 20.55 | 20.50 and 20.24 |
3’ | 13.26 | 13.25 | 13.20 |
Test microorganisms | Complexes | ||
---|---|---|---|
6-methyl-2- thiouracil |
Cu(II)L1 | Pd(II)L1 | |
Inhibition zone, mm | |||
Staphylococcus aureus ATCC 25923 | - | 8 | - |
Escherichia coli ATCC 8739 | - | 11* | 10* |
Eterococcus faecalis ATCC 19433 | 11 | 13 | - |
Salmonella enterica ssp. enterica ser. Enetritidis ATCC 13076 | - | 13 | 8 |
Pseudomonas aeruginosa ATCC 9027 | 9 | 12 | 9 |
Proteus vulgaris G | 9* | 11* | 9* |
Bacillus subtilis ATCC 6633 | 9* | 9 | 10* |
Bacillus cereus ATCC 11778 | 9* | 8 | 9* |
Listeria monocytogenes ATCC 8787 | 9* | 11 | 8 |
Klebsiella pneumoniae ATCC 13883 | 9* | 13* | 11* |
Candida albicans ATCC 10231 | 11 | 11 | 9/10* |
Saccharomyces cerevisiae | - | 9 | - |
Test microorganisms | Complexes | ||
6-propyl-2-thiouracil | Cu(II)L2 | Pd(II)L2 | |
Inhibition zone, mm | |||
Staphylococcus aureus ATCC 25923 | - | 8 | 11/16* |
Escherichia coli ATCC 8739 | - | 10* | - |
Eterococcus faecalis ATCC 19433 | - | 12 | 15 |
Salmonella enterica ssp. enterica ser. Enetritidis ATCC 13076 | 8 | 12 | 15 |
Pseudomonas aeruginosa ATCC 9027 | 8 | 12 | 14 |
Proteus vulgaris G | 10 | 9* | - |
Bacillus subtilis ATCC 6633 | 8 | 12* | 12 |
Bacillus cereus ATCC 11778 | 10* | 8 | 11/15* |
Listeria monocytogenes ATCC 8787 | 8 | 9 | 14 |
Klebsiella pneumoniae ATCC 13883 | 11* | 12* | 12* |
Candida albicans ATCC 10231 | 12 | 11 | 11 |
Saccharomyces cerevisiae | 11* | 9 | 8 |
Disclaimer/Publisher’s Note: The statements, opinions and data contained in all publications are solely those of the individual author(s) and contributor(s) and not of MDPI and/or the editor(s). MDPI and/or the editor(s) disclaim responsibility for any injury to people or property resulting from any ideas, methods, instructions or products referred to in the content. |
© 2024 MDPI (Basel, Switzerland) unless otherwise stated