2,2'-BIPYRIDINE-6,6'-DICARBOXYLICACID

2, 2'-Bipyridine-6, 6'-dicarboxylic acid (0.37 g, 1.5 mmol) in mixture of thionyl chloride (10 ml) and DMF (0.3 ml) wasrefluxed for 2.5 h. Then thionyl chloride was removed, the solid residuewas dissolved in absolute THF (15 ml) and the resulting solution was addedportionwise to a solution of tetraethyl [iminodi(methylene)]bis(phosphonate)(1 g, 3.15 mmol) and Et3N (1 ml) in absolute THF (10 ml). The mixturewas stirred at room temperature for 16 h. Then water (5 ml) was addedand the organic layer was separated, washed with water and dried overanhydrous Na2SO4. The solvent was evaporated to leave dark oil. Thendiethyl ether (5 ml) was added to the oil and the mixture was ground untilprecipitate formation. The precipitate was filtered off, washed with colddiethyl ether and dried in air to afford product 3 as white powder. Yield1 g (79%), mp 116-118C. 1H NMR (600 MHz, CDCl3) delta: 1.19 (t, 12H, CH2Me, 3J 7.0 Hz), 1.36 (t, 12H, CH2Me, 3J 7.0 Hz), 3.94-4.01 (m, 8H, CH2Me), 4.20-4.27 (m, 8H, CH2Me), 4.39 (d, 4H, 2CH2P, 2J 11.1 Hz), 4.76 (d, 4H, 2CH2P, 2J 11.2 Hz), 7.85 (d, 2H, 3, 3'-CH, 3J 7.5 Hz), 7.97(t, 2H, 4, 4'-CH, 3J 7.7 Hz), 8.50 (d, 2H, 5, 5'-CH, 3J 7.2 Hz). 13C NMR(100 MHz, CDCl3) delta: 16.2 (d, J 5.1 Hz), 16.3 (d, J 5.0 Hz), 41.3 (d, J 155.9 Hz), 44.5 (d, J 154.7 Hz), 62.2 (d, J 6.0 Hz), 62.6 (d, J 5.7 Hz), 122.1, 125.4, 138.2, 152.5, 153.1, 167.5. 31P NMR (162 MHz, CDCl3) delta:2 1.64, 21.65. MS (MALDI-TOF), m/z: 881 [M+K]+. Found (%): C, 45.72;H, 6.51; N, 14.78. Calc. for C32H54N4O14P4 (%): C, 45.61; H, 6.46;N, 14.70.

Molecular Weight:244.20
XLogP3:1.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:3
Exact Mass:244.04840674
Monoisotopic Mass:244.04840674
Topological Polar Surface Area:100
Heavy Atom Count:18
Complexity:302
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes