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CAS No. : | 6957-22-8 | MDL No. : | MFCD00136124 |
Formula : | C12H10N4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 210.23 | Pubchem ID : | - |
Synonyms : |
|
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With hydrazine hydrate In ethanol at 20℃; for 0.333333h; | |
90% | With hydrazine hydrate In methanol for 3h; Reflux; | |
90% | With hydrazine hydrate In ethanol for 24h; Inert atmosphere; |
87% | With hydrazine hydrate In ethanol at 20℃; for 24h; Inert atmosphere; | |
86% | With formic acid; hydrazine hydrate In ethanol at 20℃; for 24h; | Synthesis of L3. According to the synthetic procedure of zur Loye et al. [44]. 1 mL (11 mmol) of hydrazine hydrate was added dropwise to a solution of 4-pyridinecarboxaldehyde (2.2 mL, 22 mmol) dissolved in ethanol (15 mL). Two drops of formic acid were added and the mixture was stirred at room temperature for 24 h. The yellow solid product was filtered and washed several times with ethanol/ether (1:1). Yield: 86%. 1H NMR (400 MHz, CDCl3) δ: 8.75 (d, 4H), 8.54 (s, 2H), 7.69 (d, 4H). FT-IR (KBr, cm-1): 2941 (w), 1623 (s), 1595 (s), 1552 (m), 1417(s), 1309 (s), 1207 (m), 1082 (m), 1058 (w), 975 (s), 814 (s), 678 (s), 508 (s). Anal. Calc. for C12H10N4: C, 68.56; H, 4.79; N, 26.65. Found: C, 68.53; H, 4.81; N, 26.61%. |
86% | With formic acid; hydrazine In ethanol; water at 20℃; for 1h; | |
86% | With formic acid; hydrazine In ethanol; water at 20℃; for 24h; | 2.2 Preparation of 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene The ligand 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene (4-bpdb) was prepared according to a previously published method [19]. Typically, 0.53mL (11mmol) of hydrazine (80wt% solution in water) was added dropwise to a solution of 4-pyridinecarboxaldehyde (2.1mL, 22mmol) in ethanol (15mL). Two drops of formic acid were added and the mixture was stirred at room temperature for 24h. The yellow solid was filtered, washed several times with ethanol and diethyl ether (2×5mL), and dried in air (yield: 86%). |
79% | With formic acid; hydrazine In ethanol at 20℃; for 24h; | |
79% | With formic acid; hydrazine In ethanol at 20℃; for 24h; | 2.2. Preparation of 1,4-bis(4-pyridyl)-2,3-diaza-2,3-butadiene (4-bpdb) 1 mL (11 mmol) of hydrazine was added dropwise to a solution of pyridine-4-carboxaldehyde (2.2 mL, 22 mmol) dissolved in ethanol(15 mL). Two drops of formic acid were added and the mixture was stirred at room temperature for 24 h. The yellow solid that formed was filtered and washed several times with ethanol/ether (1:1). Yield, 79%. |
With phthaloyldihydrazine In ethanol for 1h; Heating; | ||
With hydrazine hydrate | 2.1. Materials High-purity 2-aminobenzimidazole (2-abim) and sodium dicyanamide were purchased from the Aldrich Chemical Co. Inc.and used without further purification. 1,4-bis-(4-pyridyl)-2,3-diaza-1,3-butadiene (4-bpdb) were prepared according to literature procedure [31]. The starting material for the above synthesis such as, 4-pyridine carboxaldehyde and hydrazine hydrate were purchased from Sigma-Aldrich Chemical Co. Inc. and used as received. All other chemicals and solvents were AR grade and were used as received. | |
With hydrazine hydrate | ||
0.7% | With sodium hydroxide; hydrazinium sulfate In water for 2h; | Synthesis of 3-Bphz. General procedure: A weighed sample of hydrazine sulfate (6.5 g, 0.05 mol) was dissolved in water(250 mL). The obtained solution was heated to 70°C on a magnetic stirrer. 3-Pyridinecarboxaldehyde(9.4 mL, 0.1 mol) was added to the solution. Then a solution of NaOH was added to neutral pH, and the mixture was stirred for ~2 h. The obtained mixture was filtered, washed with water to remove sodium sulfate,and dissolved in ethanol (50 mL). The solution was left to stay for slow evaporation at room temperature for crystallization. |
With acetic acid; hydrazine In ethanol Reflux; | ||
With hydrazine hydrate In ethanol Reflux; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In ethanol; dichloromethane EtOH soln. of Co(NO3)2*6H2O was mixed with CH2Cl2 soln. of ligand, stirred at room temp. for 3 d; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In tetrahydrofuran; ethanol EtOH soln. of Ni(NO3)2*6H2O was mixed with THF soln. of ligand, stirred at room temp. for 2 wks; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dibenzo-24-crown-8 In methanol; nitrobenzene Zn complex react with equimolar amount of hydrazine in CH3OH, to resulting soln. nitrobenzene and crown added; soln. evapd.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In dichloromethane; acetonitrile a soln. of Ag salt in MeCN added to a soln. of ligand in CH2Cl2, stirredfor 10 min; filtered; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | In acetone under Ar, in the dark; suspn. of ligand (10 equiv.) in acetone stirred for 30 min; Ru complex added; stirred for 2 h; pptd. with toluene; cooled; filtered; dried; dissolved in acetone; pptd.with Et2O; filtered; dried in vac. over P4O10; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In ethanol; water soln. of ligand in EtOH added to stirred aq. soln. of Mn salt, then aq. soln. of NaN3 added dropwise with stirring; crystals sepd., mother liquor evapd. slowly at room temp. for several d;elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
29% | In toluene under Ar; Re complex refluxed with ligand (10-fold excess) in toluene for 2 h; cooled; filtered; ppt. washed with min. amt. of toluene; suspended in CH2Cl2; column chromd. (neutral alumina, MeCN-CH2Cl2 1:6); yellow fraction rotoevapd.; dissolved in acetone; pptd. with hexane; filtered; dried in vac. over P4O10; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
54% | In dichloromethane addn. of copper compd. to soln. of triphenylphosphine in CH2Cl2 with stirring, stirring for 1 h, addn. of pyridine deriv. with stirring at room temp.; slow evapn., elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57% | In hexane under Ar; Re complex refluxed with ligand (2-fold excess) in hexane for 1 h; ppt. collected; washed with min. amt. of hot hexane; dissolved in MeCN-CH2Cl2; column chromd. (alumina, MeCN-CH2Cl2 1:1); first yellow fraction evapd.; pptd. with hexane; filtered; dried in vac. over P4O10; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 12% 2: 14% | With AgCF3SO3 In tetrahydrofuran byproducts: AgCl; Re complex (0.443 mmol) and AgCF3SO3 (0.443 mmol) refluxed in THF (30 min); 4-pyridinealdazine (0.664 mmol) added; refluxed (2 h); AgCl filteredoff; solvent removed; dissolved in MeOH/H2O (3:1, v/v); aq. soln. of NH 4PF6 (2 g) added; kept in freezer; filtered; washed with H2O and Et2O; dissolved in CH3CN/CH2Cl2 (1:4, v/v); chromd. (silica gel (Kieselgel 60), CH3CN/CH2Cl2 1:4 v/v); yellow fraction collected; concd. to dryness; dissolved in acetone; pptd. with hexane; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In methanol 1 equiv. of N-compd. and 1 equiv. of Hg-compd. were placed in the main arm of the branched tube, methanol was filled into the arm, tube was sealed and immersed into an oil bath at 60 °C and the other arm was kept at room temp. for 2-3 d; crystals were filtered off, washed with acetone and ether, dried in air,elem. anal.; | |
42% | In methanol; chloroform 1 equiv. of Hg-salt in MeOH was layered onto the soln. of N-compd. in CHCl3; crystn. for 2 d, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In dichloromethane; toluene (N2); Ag salt (1 equiv.) was added to soln. of Pd complex in toluene/CH2Cl2 (5/2) at 25°C; stirred for 30 min; filtered through Celite; Nligand (0.5 equiv.) was added; stirred for 30 min; hexane added; filtered; residue dried (vac.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In methanol High Pressure; diazabutadiene and mixt. Hg(OAc)2/Hg(SCN)2 were placed in main arm ot branch tube, MeOH was added to fill arms, tube was sealed and ligand-containing arm heated in oil bath at 60°C for 5-6 d, while other was at ambient temp.; crystals deposited in cooler arm was filtered off, washed with acetone and ether, dried in air, elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | In tetrahydrofuran Re complex refluxed for 2 h with ligand in THF; filtered, concd. (vac.), dissolved in acetone, pptd. (toluene), recrystd. (acetone and ether), filtered, washed, dried (vac.); elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60.3% | In N,N-dimethyl-formamide suspn. Zn(NO3)2*6H2O, 4,4'-(hexafluoroisopropylidene)bis(benzoic acid) and 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene in DMF was heated at 100°C for 60 h; ppt. was filtered, washed with MeOH and dried in air; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol Ar; MeOH soln. of ligand purged with Ar, mixed with soln. of Cu compd. (2:1 molar ratio), stirred at room temp. for 2 h; ppt. filtered off, washed (MeOH), dried (vac.), elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50% | With NaOH In water High Pressure; mixt. of Cd(NO3)2*4H2O, NC5H4COOH, pab ligand and 0.1 M NaOH heated to 110 °C for 24 h in Teflon-lined bomb; cooled to room temp. over 1 d, washing (water, methanol), drying in air,elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | In neat (no solvent) High Pressure; synthesis according to D.K.Orsa et al., Inorg. Chem. Commun. 10 (2007) 821: solvothermal conditions; mixt. heated under reflux, stirred for 8 h; soln. cooled to room temp., hexane added, solid filtered, suspnd. in CH2Cl2, filtered, mixture of conformation isomers; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | In nitromethane-d3 nitromethane-d3 soln. of azine deriv. and Pt complex stirred at room temp. for 2 h; solvent removed under N2 flow; elem. anal.; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In dichloromethane at 20℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In methanol; nitromethane at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | In methanol; nitromethane at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | In methanol; nitromethane at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | In methanol; nitromethane at 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
42% | In methanol at 4℃; for 336h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
36% | In methanol; propan-1-ol at 4℃; for 168h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
22% | In methanol; propan-1-ol at 4℃; for 168h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | In methanol; propan-1-ol at 4℃; for 168h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74% | With (1S,3R)-(-)-camphoric acid In ethanol at 20℃; for 168h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | With (1S,3R)-(-)-camphoric acid In ethanol at 20℃; for 168h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | In methanol; water for 336h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
67% | In N,N-dimethyl-formamide at 90℃; Sonication; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | Stage #1: methanol; dimethyltin dichloride; 4-pyridinealdazine In ethanol at 20℃; for 0.166667h; Schlenk technique; Inert atmosphere; Stage #2: cupferron at 20℃; for 1h; Schlenk technique; Inert atmosphere; | 2.3.2. Preparation of [μ-(4-bpdb){Me2Sn(cupf)2}2]MeOH (2) All manipulations were performed under an atmosphere of dry nitrogen using standard Schlenk line technique. For preparation of title complex, a solution of 4,40-bipyridine (0.16 g, 1.0 mmol) in ethanol (20 mL) was added to a solution of dimethyltin(IV) dichloride (0.22 g, 1.0 mmol) in ethanol (10 mL). A white precipitation was rapidly formed. The mixture was stirred for 10 min at room temperature and then NH4[PhN(O)NO] salt (0.31 g, 2.0 mmol) was added to the reactor. The NH4Cl promptly precipitated and the resulting yellow solution was stirred for one hour at room temperature.The precipitate was filtered off and the mother liquor was left to evaporate slowly at room temperature. After one week, yellow crystals of title complex were isolated (yield 75%; m.p.130-132 C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
43% | In methanol; N,N-dimethyl-formamide at 120℃; for 48h; High pressure; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
75% | In methanol; dichloromethane for 360h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
33% | at 80℃; for 96h; | |
33% | at 80℃; for 72h; | 2.3. Preparation of [Zn(NH2-BDC)(4-bpdb)].2DMF (TMU-17-NH2) The TMU-17-NH2, [Zn(NH2-BDC)(4-bpdb)].2DMF was preparedby following the published protocol [33]. Briefly, Zn(NO3)2·6H2O(0.297 g, 1 mmol), 4-bpdb (0.210 g, 1 mmol), NH2-BDC (0.181 g,1 mmol) were dissolved in 15 mL DMF. The mixture was placed in a Teflon reactor and heated at 80 °C for 3 days, and then it was gradually cooled to room temperature during 24 h. The crystals were obtained in a 33% yield. FT-IR (cm-1): 3462.05 (s), 3364.90 (s), 1676.84 (vs),1609.95 (vs), 1574.38 (vs), 1425.94 (vs), 1380.69 (vs), 1253.26 (s),1094.03 (m), 1014.26 (m), 830.72 (s), 772.04 (s), 688.79 (s), 519.39(s). |
at 80℃; High pressure; | 2.2.1. Preparation of [Zn(NH2-BDC)(4-bpdb)].2DMF (Zn-MOF) As reported by Morsali et al,[45] the high quality single crystals were prepared by solvothermal reaction of Zn(NO3)2.6H2O(0.297 g, 1 mmol), 4-bpdb (0.210 g, 1 mmol), and H2BDC-NH2(0.181 g, 1 mmol) at 80 °C in 15 ml DMF. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In methanol; propan-1-ol for 360h; | 2.2 Synthesis of Compound 1⊃G[{Zn2(L)4(OTf)4}.2(DCM).x(G)2]n (1⊃G) DCM solution of the ligand (21.023mg, 1mL) was taken into a glass tube, onto that 1-propanol (1mL) was carefully layered and over the 1-propanol layer, solution of Zn (OTf)2 (36.353mg, 1mL) inMeOH was very carefully layered. Block shaped yellow crystals suitable for X-ray studies were obtained after 15 days in 70% yield. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | In ethanol; water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In ethanol; water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In ethanol at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In ethanol; water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | With cadmium(II) nitrate tetrhydrate In ethanol; water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With sodium hydroxide In ethanol; water at 100℃; for 48h; High pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: water; sodium salt of 5-nitro-1,3-benzenedicarboxylic acid; 4-pyridinealdazine In methanol for 0.5h; Stage #2: iron(II) perchlorate hydrate In methanol at 20℃; for 240h; Sealed tube; | 2.3.1. [Mn(4-bpdh)(nip)(H2O)2]•H2O}n (1) General procedure: An aqueous solution (20 mL) of Na2nip (1 mmol, 0.255 g) was mixed with a methanolic solution (20 mL) of 2,5-bis-(4-pyridyl)-3,4-diaza-2,4-hexadiene (4-bpdh) (1 mmol, 0.238 g) and stirred for 30 min to mix it well. MnCl24H2O (1 mmol, 0.198 g) was dissolved in 20 mL of water in a separate beaker. In a crystal tube, 3 ml of the Mn(II) solution was then slowly and carefully layered with 6 ml of above mentioned mixed-ligand solution using 3 mlof buffer solution (1:1 of H2O and MeOH) between the two solutions.The tube was sealed and kept undisturbed at room temperature and after seven days colorless block shaped single crystals suitable for X-ray diffraction analysis were obtained at the wall of the tube. The crystals were separated and washed with amethanol-water (1:1) mixture and dried under air (Yield: 63%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With hydrazine hydrate In ethanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | In methanol; water at 20℃; for 0.5h; | 2.3.4. [Zn(4-bpdb)(N(CN)2) (4) An aqueous solution (5 mL) of Zn(NO3)*6H2O (1 mmol, 0.297 g) and sodium dicyanamide (2 mmol, 0.17 g) was mixed with constant stirring. Then methanolic solution of 4-bpdb (1 mmol, 0.210 g) was added to the solution and stirred for about 30 min at room temperature. After three days, yellowish block shaped crystals suitable for X-ray diffraction were obtained from the filtrate. Yield 85%. Anal. Calc. for 4 C16H10N10Zn: C, 47.13; H, 2.45;N, 34.35. Found: C, 47.35; H, 2.59; N, 34.86%. IR spectra (in cm-1) ν(N(CN)2)1 2298, 2235, 2159; ν(C=C), 1607; ν(C=N) 1423. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In methanol; water at 20℃; for 0.5h; | 2.3.4. [Zn(4-bpdb)(N(CN)2) (4) General procedure: An aqueous solution (5 mL) of Zn(NO3)*6H2O (1 mmol, 0.297 g) and sodium dicyanamide (2 mmol, 0.17 g) was mixed with constant stirring. Then methanolic solution of 4-bpdb (1 mmol, 0.210 g) was added to the solution and stirred for about 30 min at room temperature. After three days, yellowish block shaped crystals suitable for X-ray diffraction were obtained from the filtrate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | In tetrahydrofuran; N,N-dimethyl-formamide at 84.84℃; for 72h; High pressure; Autoclave; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol at 60℃; for 168h; Sealed tube; | 2.2. Synthesis of complexes 1-5 General procedure: For the preparation of all compounds, a new and one-step method namely branch tube method has been used. One of the main advantages of this method is the high purity of prepared compounds. According to this method, for the preparation of complex 1, (C6H16N)+[Sn2Cl6(CH3O)2(C15H9O2)], a mixture of stannic chloride pentahydrate (1.0 mmol), 9-anthracenecarboxylic acid (0.5 mmol) and triethylamine (1 mmol) were loaded into the longer arm of tube and then the tube was carefully filled with dry methanol and sealed. The longer arm of the tube was submerged in an oil bath at 60° C. After a week, the yellow crystals were gathered from cold and shorter arm of the tub. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | In water at 120℃; for 60h; Autoclave; High pressure; | Preparation of complex 1 A mixture of Co(OAc)2*6H2O (0.14 g, 0.5 mmol), H3BTC (0.11 g, 0.5 mmol) and 4-bpdb (0.11 g, 0.5 mmol) in H2O (15 mL) was sealed in a Teflon-lined autoclave and heated to 120 C for 60 h and then gradually cooled down to room temperature. Purple crystals were obtained. Yield: 0.10 g, 71% (based on Co(OAc)2*6H2O). Anal. calcd for C21H16-N4O7Co: C, 50.92; H, 3.26; N, 11.31%. Found: C, 50.95; H, 3.23; N, 11.37%. IR (KBr, cm-1) 3447 m, 2922 s, 2853 s, 1648 m, 1614 m, 1540 m, 1514 m, 1463 m, 1371 m, 719 m, 673w, 561w, 516w. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In methanol; water |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In methanol; dichloromethane for 24h; | [Co(acac)2(L1)]n (2). General procedure: A dichloromethane solution (6 mL) of L1 (33.6 mg, 0.10 mmol) was allowed to diffuse slowly into a methanol solution (6 mL) of Co(acac)2·2H2O (29.5 mg, 0.10 mmol) through an intermediate layer of methanol/dichloromethane (1:1, 4 ml). Orange block crystals formed within 2 days, yield 63%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In N,N-dimethyl-formamide at 120℃; for 504h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
77% | In ethanol at 115℃; for 48h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sodium hydrogencarbonate In methanol; water at 70℃; for 6h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | With sodium hydroxide In methanol; water at 20℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
45% | With sodium hydroxide In ethanol; water for 336h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine at 30℃; for 2h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | In methanol |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | In methanol | [μ2-1,2-Bis(4-pyridylmethylene)hydrazine]dimethylbis(N-nitroso-N-phenylhydroxylaminato)tin(IV) (5, C40H42N12O8Sn2) General procedure: For thepreparation of compound 2, 4-(dimethylamino)pyridine(1 mmol) was dissolved in 10 cm3 methanol and added to asolution containing complex 1 in 10 cm3 methanol whilestirring, leading to the formation of a yellow solution. Thesolid product as compound 2 was collected after removal ofthe solvent under reduced pressure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triethylamine In ethanol; water for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With triethylamine In ethanol; water for 72h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | at 20℃; for 1h; | |
83% | at 20℃; for 1h; Sonication; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With urea In ethanol at 20℃; for 168h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With urea In ethanol at 20℃; for 168h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | at 80℃; for 72h; Sealed tube; | |
at 80℃; for 72h; High pressure; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.75% | In N,N-dimethyl-formamide at 120℃; for 48h; Autoclave; | 3. Synthesis of [Zn2(fum)2(4-bpdb)]·2H2O}n (TMU-42) A solution of Zn(NO3)2·6H2O (2 mmol, 0.594 g), 1,4-bis(4-pyridyl)-3,4-diaza-1,3-butadiene (4-bpdb) (1 mmol, 0.210 g) and fumaric acid (2 mmol, 0.232 g) were dissolved in 20 mL DMF in a Teflon-lined autoclave. It was heated under autogenous pressure to 120 °C for 48 h. Cooling to room temperature at the rate of 5 °C/h afforded the product as orange good crystals and separated and washed with DMF. 4-bpdb was prepared by the reported method [47,48]. ∼75% yield, d.p >350 °C. IR (cm-1) selected bonds: ν = 682(m), 796(w), 1173(w), 1297(m), 1400(s), 1629(s), 1735(w), 2927(w) and 3434(m). Anal. Calc. For C20H14N4O10Zn2: C, 41.05; H, 2.41; N, 9.58. Found: C, 40.85; H, 2.51; N, 10.01%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In methanol at 20℃; for 168h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | In N,N-dimethyl-formamide at 20℃; for 0.5h; Sealed tube; | |
0.42% | Stage #1: cadmium(II) acetate dihydrate; 4-pyridinealdazine In ethanol Stage #2: water | Synthesis of complex IV. A weighed sample ofCd(CH3COO)2 2H2O (0.026 g, 0.1 mmol) was dissolved in ethanol (10 mL) with stirring (70°C). The solution was added by 4-Bphz (0.021 g, 0.1 mmol),which was accompanied by precipitation. After water(2 mL) was added, the precipitate dissolved and thesolution turned transparent. The obtained solutionwas filtered and left to stay for slow evaporation atroom temperature. Yellow crystals suitable for X-ray diffraction analysis precipitated from the solution in a week. The yield was ~42%. The substance is soluble inDMF and DMSO and insoluble in alcohols.IR (ν, cm-1): 3088, 3035, 1630, 1605, 1551, 1485,1410, 681, 679. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.37% | Stage #1: cadmium(II) nitrate hexahydrate; 4-pyridinealdazine In methanol at 70℃; Stage #2: water | Synthesis of complex V. A weighed sample ofCd(NO3)2 6H2O (0.035 g, 0.1 mmol) was dissolved inmethanol (10 mL) with stirring (70°C). The solution was added by 4-Bphz (0.021 g, 0.1 mmol), which was accompanied by precipitation. After DMF (3 mL) wasadded, the precipitate dissolved and the solutionturned transparent. The transparent solution was filteredand left to stay for slow evaporation at room temperature.Yellow crystals suitable for X-ray diffractionanalysis precipitated from the solution in 3 weeks. Theyield was ~37%. The substance is soluble in DMF andDMSO and insoluble in alcohols.IR (ν, cm-1): 3099, 3043, 1652, 1611, 1558, 1423,1386, 1342, 1304, 1021. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | at 20℃; for 1461h; | 2.2. Synthesis of [CdL(NCS)2(DMSO)2]n (1) Method 1: 0.020 g (0.0951 mmol) of L was dissolved in 2.5 mL ofdimethyl sulfoxide. Then 0.0185 g (0.190 mmol) of KSCN was dissolvedin 2.5 mL of dimethyl sulfoxide and when it was completelysolved, 0.0293 g (0.0949 mmol) of Cd(NO3)24H2O was added tothis solution. Then the solution including ligand was added dropwiseto solution containing mix salts and was stirred in room temperaturefor 30 min. The solution was transferred to clean vial thatwas suitable for crystal growing according to slow evaporationmethod. After two months, the yellow plate single crystals of 1 were appeared and washed with DMSO and n-hexane (yield:65%, mp > 260 C). Elemental analysis: calculated: C, 36.33; H,3.73; N, 14.12%; found: C, 36.18; H, 3.69; N, 14.02%. IR (KBr,cm1): 2059(s), 1603(s), 1547(w), 1412(m), 1309(m), 1224(m),1097(w), 1062(w), 1006(s), 948(s), 831(m), 686(m), 521(m), 459(w) (Fig. S1). Other techniques and solvents resulted in plate singlecrystals of 1 were listed in Table S1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | at 20℃; for 336h; | 2.2. Synthesis of [CdL(NCS)2(DMSO)2]n (1) Method 1: 0.020 g (0.0951 mmol) of L was dissolved in 2.5 mL ofdimethyl sulfoxide. Then 0.0185 g (0.190 mmol) of KSCN was dissolvedin 2.5 mL of dimethyl sulfoxide and when it was completelysolved, 0.0293 g (0.0949 mmol) of Cd(NO3)24H2O was added tothis solution. Then the solution including ligand was added dropwiseto solution containing mix salts and was stirred in room temperaturefor 30 min. The solution was transferred to clean vial thatwas suitable for crystal growing according to slow evaporationmethod. After two months, the yellow plate single crystals of 1 were appeared and washed with DMSO and n-hexane (yield:65%, mp > 260 C). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | In N,N-dimethyl-formamide at 20℃; for 1461h; | 2.4. Synthesis of [CdL(m-SeCN)2]n (3) 0.020 g (0.0951 mmol) of L was dissolved in 2.5 mL of N,N’-dimethylformamide. Then 0.0277 g, (0.1922 mmol) of KSeCN wasdissolved in 2.5 mL of DMF. After that it solved completely0.0293 g, (0.0949 mmol) of Cd(NO3)24H2O was added to previoussolution. Then the solution including ligand was added dropwiseto solution containing mix salts and was stirred in room temperature for 30 min. The resulted solution was filtered andtransferred to a clean vial that was suitable for crystal growingaccording to slow evaporation method. After about two monthsthe orange plate single crystals of 3 were formed and washed withDMF and n-hexane (yield: 70%, mp > 260 C). Elemental analysis:calculated: C, 31.57; H, 1.89; N, 15.78%; found: C, 31.40; H, 1.85;N, 15.70%.IR (KBr, cm1): 2101(s), 1658(w), 1597(s), 1555(w),1418(m), 1310(m), 1221(m), 1075(w), 1009(m), 950(w), 817(m),688(m), 587(w), 514(m), 456(w) (Fig. S3). Other condition and solventresulted in single crystals of 3 were listed in Table S2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
48% | Stage #1: cadmium(II) nitrate tetrhydrate; 4-pyridinealdazine In N,N-dimethyl-formamide at 80℃; for 0.166667h; Stage #2: benzene-1,3,5-tricarboxylic acid In N,N-dimethyl-formamide at 90℃; for 72h; Autoclave; High pressure; | 2.3 Synthesis of [Cd3(BTC)2(4-bpdb)2] (Cd-MOF) Cd(NO3)2·4H2O (0.102g, 0.33mmol), benzene-1,3,5-tricarboxylic acid (H3BTC, 0.046g, 0.22mmol), and 1,4-bis(4-pyridyl)-2,3-diaza-1,3-butadiene (4-bpdb, 0.046g, 0.22mmol) were dissolved in 7mL DMF in three separate test tubes. The three solutions were warmed at 80°C for 10min. Then the solution of 4-bpdb was added to that of Cd(NO3)2·4H2O and, after stirring for 10min, also that of H3BTC was added to the mixture. The resulting yellowish solution was placed in a teflon-lined stainless steel autoclave and heated at 90°C for 72h. The mixture was gradually cooled to room temperature over 24h. Yellow needle-shaped single crystals of [Cd3(BTC)2(4-bpdb)2] suitable for single crystal X-ray diffraction analysis were obtained, collected by filtration, and dried in air (0.18g, yield: 48% based on Cd). Elemental analysis (%) calc. for C51H47Cd3N11O15: C 44.03, H 3.41, N 11.07; found: C 44.16, H 3.30, N 11.09. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | for 168h; | 4.7 [Cd(4-bphz)(SO4)(H2O)]·(H2O·C2H5OH)}n (7) The synthesis of this compound was more specific. In a glass tube was added a rubber plate about 1cm thick (the plate was cut from a rubber stopper, preventively washed and cleaned well). To this tube was added the solution of 4-bphz ligand, 0.032g (0.15mmol) dissolved in 5mL of ethanol, so that the solution level would be at the same height as the rubber plate. Thereafter, with a graduated pipette, inserted to the bottom of the test tube, the solution of CdSO4·8/3H2O, 0.025g (0.1mmol) and 5mL of water were added slowly under the ligand solution. After a week, orange-red and yellow crystals were formed on the surface of the rubber plate and at the bottom of the vessel. For X-ray diffraction were selected suitable orange-red crystals. (0022) Yield: 38%. Anal. Calc. for C14H20CdN4O7, (%): C, 33.58; H, 4.03; O, 22.36; N, 11.19; S, 6.40. Found: C, 33.40; H, 3.89; O, 22.21; N, 11.00; S, 6.25. IR (ATR, cm-1) 3267m, 3090m, 3062m, 3034m, 1631s, 1611s, 1555m, 1480 w, 1424s, 1313m, 1243m, 1157s, 1098 vs, 1016 vs, 956 vs, 825s, 690s. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | In chloroform; acetonitrile at 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In ethanol; water for 72h; Sealed tube; | 2.3. Synthesis of [Zn2(4-bphz)(2-tpc)4]n (1) In a beaker, 0.06 g (0.2 mmol) of Zn(NO3)26H2O and 0.06 g(0.4 mmol) of Na(2-tpc) were dissolved in 8 mL of H2O. In anotherbeaker, 0.042 g (0.2 mmol) of 4-bphz was dissolved in 8mL of EtOH.The 4-bphz ligand solution was added, without stirring, to the solutionof the first beaker. The beaker was covered with parafilm. After3 days, yellow crystals formed. Yield: ~60%. Anal. calc. forC16H11N2O4S2Zn (%): C, 45.24; H, 2.61; N, 6.59; O, 15.07; S, 15.10.Found (%): C, 44.92; H, 2.41; N, 6.34; O 14.87; S, 14.89. IR-ATR(cm1): 3090 w, 3067 w, 1625 s, 1616 s, 1525 m, 1423 vs, 1388vs, 1347 m, 1312 m, 1224 m, 1208 w, 1119 w, 1064 w, 1032 m,976 w, 954 w, 859 w, 829 m, 799 m, 766 vs, 708 vs, 694 s, 656 s. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | In ethanol; water for 72h; Sealed tube; | 2.3. Synthesis of [Zn2(4-bphz)(2-tpc)4]n (1) General procedure: In a beaker, 0.06 g (0.2 mmol) of Zn(NO3)26H2O and 0.06 g(0.4 mmol) of Na(2-tpc) were dissolved in 8 mL of H2O. In anotherbeaker, 0.042 g (0.2 mmol) of 4-bphz was dissolved in 8mL of EtOH.The 4-bphz ligand solution was added, without stirring, to the solutionof the first beaker. The beaker was covered with parafilm. After3 days, yellow crystals formed. Yield: ~60%. |
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