Sulfur Bridged Multidentate Ligands Based on (Bi)pyridyl-(Bi)-1,3,4-Thiadiazolyl Conjugates
Abstract
:Introduction
Results and Discussion
Proton | L1 | L2 | L3 | L4 | L5 | L6 | L7 | L8 |
---|---|---|---|---|---|---|---|---|
3 | 7.34 d J = 8.0 | 7.41 d J = 8.0 | 8.31 d J = 7.5 | 8.37 d J = 7.5 | 7.41 d J = 8.0 | 7.48 d J = 7.5 | 8.16 d J = 8.0 | 8.20 d J = 8.0 |
4 | 7.62 t J = 7.5 | 7.67 t J = 7.8 | 7.79 dt J = 7.5, 1.5 | 7.81 t J = 7.5 | 7.65 dt J = 7.5, 2.0 | 7.67 dt J = 7.5, 1.0 | 7.76 t J = 8.0 | 7.79 t J = 8.0 |
5 | 7.34 d J = 8.0 | 7.41 d J = 8.0 | 7.44 d J = 8.0 | 7.49 d J = 7.5 | 7.20 t J = 6.0 | 7.22 t J = 7.5 | 7.39 d J = 7.5 | 7.45 d J = 8.0 |
6 | 8.54 dd J = 3.5, 2.0 | 8.57 dd J = 4.0, 1.0 | ||||||
3’ | 8.31 d J = 7.5 | 8.37 d J = 7.5 | 8.37 d J = 7.5 | |||||
4’ | 7.79 dt J = 7.5, 1.5 | 7.81 t J = 7.5 | 7.68 t J = 7.5 | 7.69 t J = 8.0 | ||||
5’ | 7.44 d J = 8.0 | 7.49 d J = 7.5 | 7.16 d J = 7.5 | 7.17 d J = 7.5 | ||||
CH2 | 4.57 s | 4.72 s | 4.69 s | 4.83 s | 4.58 | 4.72 s | 4.68 s | 4.83 s |
CH3 | 2.73 s | 2.84 s | 2.73 s | 2.84 s | 2.61 s | 2.61 s |
Lig. | Yield (%) (Cryst. Solv. ) | Melting Point (°C) | Molecular Formula | %C Found(Calcd) | %H Found(Calcd) | %N Found(Calcd) | 13C NMR |
---|---|---|---|---|---|---|---|
L1 | 84 (EtOH) | 94−95 | C13H13N5S6 | 36.13 (36.17) | 3.33 (3.03) | 16.04 (16.22) | 167.0, 164.0, 155.6, 137.7, 122.1, 39.8, 16.7 |
L2 | 63 (DMF) | 207−212 | C17H13N9S6 | 33.82 (34.04) | 2.22 (2.18) | 21.06 (21.02) | 170.1, 168.2, 158.8, 158.1, 155.2, 137.8, 123.3, 39.7, 16.7 |
L3 | 90 (EtOH-CHCl3) | 157−158 | C18H16N6S6 | 42.83 (42.49) | 3.06 (3.17) | 16.74 (16.52) | 166.9, 164.4, 155.2, 154.9, 137.7, 123.1, 120.0, 40.3, 16.7 |
L4 | 71 (DMF) | 257−258 | C22H16N10S8 | 39.17 (39.03) | 2.03 (2.38) | 20.92 (20.69) | 170.1, 168.6, 158.6, 158.2, 155.2, 154.4, 137.9, 123.2, 120.2, 40.2, 16.7 |
L5 | 95 (MeOH-H2O) | 80−81 | C14H12N4S3 | 50.91 (50.58) | 3.57 (3.64) | 16.94 (16.85) | 164.9, 155.4, 149.5, 136.9, 123.3, 122.7, 39.9 |
L6 | 80 (AcOEt) | 163−165 | C26H22N6S3 | 61.01 (60.67) | 3.90 (4.31) | 16.41 (16.33) | 165.4, 157.9, 156.0, 154.8, 154.7, 137.6, 137.0, 123.4, 122.7, 119.9, 118.1, 40.4, 24.6 |
L7 | 73 (Dioxane) | 159−160 | C16H12N6S4 | 46.52 (46.13) | 2.49 (2.90) | 19.74 (20.17) | 168.3, 158.6, 155.0, 149.6, 136.9, 123.3, 122.8, 39.8 |
L8 | 80 Dioxane/DMF | 248−250 | C28H22N8S4 | 55.98 (56.16) | 3.85 (3.70) | 18.92 (18.71) | 168.8, 158.6, 157.9, 156.2, 154.7, 154.2, 137.7, 137.0, 123.5, 122.7, 120.0, 118.1, 40.3, 26.6 |
Conclusions
Experimental
General
5-Mercapto-5'-methylthio-2,2'-bi-1,3,4-thiadiazole (2).
General Procedure for the Nucleophilic Displacement Reactions: Synthesis of 2,6-Bis[5-methylthio-1,3,4-thiadiazol-2-ylthio)methyl]pyridine (L1)
Acknowledgements
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- Sample availability: Available from the authors.
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Mamo, A.; Pappalardo, A.; Clasadonte, M.T. Sulfur Bridged Multidentate Ligands Based on (Bi)pyridyl-(Bi)-1,3,4-Thiadiazolyl Conjugates. Molecules 2003, 8, 310-317. https://doi.org/10.3390/80300310
Mamo A, Pappalardo A, Clasadonte MT. Sulfur Bridged Multidentate Ligands Based on (Bi)pyridyl-(Bi)-1,3,4-Thiadiazolyl Conjugates. Molecules. 2003; 8(3):310-317. https://doi.org/10.3390/80300310
Chicago/Turabian StyleMamo, Antonino, Andrea Pappalardo, and M. Teresa Clasadonte. 2003. "Sulfur Bridged Multidentate Ligands Based on (Bi)pyridyl-(Bi)-1,3,4-Thiadiazolyl Conjugates" Molecules 8, no. 3: 310-317. https://doi.org/10.3390/80300310