Benzimidazole-5,6-dicarboxylic acid

Europium oxide (0.1 mmol, 35.2 mg), H3bidc (41.2 mg, 0.2 mmol) and 2 ml of dilute sulfuric acid(0.2 M) were added to water (10 ml) at room temperature.After continuous stirring for 10 min, the mixture was sealed ina Teflon-lined stainless steel vessel (23 ml), heated at 180 C for 3 d under autogenous pressure and then cooled slowly toroom temperature. Brown block-shaped crystals of 2 wereharvested in a yield of 78% (based on Eu). Elemental analysis(%) calculated for C9H5EuN2O8S: C 23.85, H 1.11, N 6.18;found: C 23.96, H 1.20, N 6.10. IR (KBr, cm-1): 3128 (w, br), 1618 (m), 1507 (s), 1465 (w), 1397 (vs), 1161 (m), 1108 (m), 1066 (m), 890 (m), 770 (m), 620 (m), 608 (m), 562 (w).Europium oxide (0.1 mmol, 35.2 mg), H3bidc (41.2 mg, 0.2 mmol) and a solution (1 ml) of oxalic acid(0.1 M) were dissolved in water (10 ml) at room temperature.After continuous stirring for 10 min, the mixture was sealed ina Teflon-lined stainless steel vessel (23 ml), heated at 180 C for 3 d under autogenous pressure and cooled slowly to room temperature. Yellow block-shaped crystals of 1 were harvestedin a yield of 80% (based on Eu). Elemental analysis (%)calculated for C10H8EuN2O8: C 27.54, H 1.85, N 6.42; found: C27.32, H 1.90, N 6.51. IR (KBr, cm-1): 3130 (m, br), 1680 (s), 1620 (m), 1575 (s), 1410 (w), 1380 (m), 1209 (m), 1102 (s), 1110(vs), 1000 (m), 890 (s), 813 (m), 650 (w), 580 (w).A mixture of H3bidc (0.0206g, 0.1mmol), Sc(NO3)·6H2O (0.5ml, 0.2M) was added to H2O (9ml), KOH (20mul, 1M) in a 23ml Teflon-lined autoclave and then heated under autogenous pressure at 160C for 24h, then cooled to room temperature under ambient conditions. Colorless block crystals were obtained by filtration and washed with distilled water, and dried in air. Yield: 80% for 2 (based on Sc(NO3)·6H2O). Elemental analysis (%) for 2: Anal. Calc. C, 38.03; H, 2.46; N, 9.86; Found: C, 37.82; H, 2.55; N, 9.72. IR (KBr pellet, cm-1) for 2 (4000-400cm-1): 3487 (s), 1793 (w), 1535 (s), 1420 (s), 1269 (m), 1171 (w), 1045 (w), 956 (m), 809 (m), 773 (w), 615(w) (Fig. S6).A mixture of H3bidc (0.0824g, 0.4mmol), InCl3·4H2O (0.2ml, 0.1M) was added to CH3CN (4ml), HNO3 (0.4ml, 1M) and H2O (1ml) in a 23ml Teflon-lined autoclave and then heated under autogenous pressure at 120C for 24h, then cooled to room temperature under ambient conditions. Colorless block crystals were obtained by filtration and washed with distilled water, and dried in air. Yield: 85% for 1 (based on InCl3·4H2O). Elemental analysis (%) for 1: Anal. Calc. C, 37.47; H, 1.73; N, 9.71; Found: C, 37.35; H, 1.55; N, 9.78. IR (KBr pellet, cm-1) for 1 (4000-400cm-1): 3254 (s), 1594 (s), 1384 (s), 1329 (s), 1035 (m), 1235 (m), 921 (w), 847 (w), 786 (s), 639 (m), 500 (m) (Fig. S5).

Molecular Weight:206.15
XLogP3:0.5
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:2
Exact Mass:206.03275668
Monoisotopic Mass:206.03275668
Topological Polar Surface Area:103
Heavy Atom Count:15
Complexity:294
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes