A new hexaaminomacrocycle for ditopic binding of bromide

Tetrahedron Letters

Volumn 50, Issue 47, 2009, Pages 6537-6539

  Gibson, Don ^a   Dey, Kalpana R ^a   Fronczek, Frank R ^b   Hossain, Md Alamgir ^a  

^a JACKSON STATE UNIVERSITY   (United States)

^b LOUISIANA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BROMIDE; HEXAAMINOMACROCYCLIC COMPOUND; HYDROBROMIC ACID; MACROCYCLIC COMPOUND; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BINDING; CHEMICAL STRUCTURE; HYDROGEN BOND; MOLECULAR INTERACTION; PROTON TRANSPORT; SYNTHESIS;

EID: 74749110040     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.09.041     Document Type: Article

References (34)

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25. The synthesis of L was accomplished by the condensation reaction performed under high dilution conditions. In a typical reaction, N-methyl-2,2'-diaminodiethylamine (1.00 g, 8.53 x 10-3mol) in CH3OH (200 mL) and terephthaldehyde (1.15 g, 8.53 x 10-3mol) in CH3OH (200 mL) were added simultaneously to 400 mL of CH3OH over 4 h. The resulting mixture was stirred at room temperature for another 24 h. After the evaporation of the solvent, the oily product was dissolved in CH3OH (100 mL) and reduced with NaBH4 overnight at room temperature. The solvent was removed in vacuo, and the resulting oily product was dissolved in water (100 mL). The aqueous phase was extracted by CH2Cl2 (3 x 100 mL). The organic layers were combined and dried by adding anhydrous MgSO4 (2 g). After the filtration, the solvent was evaporated under reduced pressure resulting in a light yellowish powder. The crude product was purified by column chromatography (neutral alumina, 2% CH3OH in CH2Cl2).Yield: 0.67 g, 60%. 1H NMR (300 MHz, CDCl3, TMS): δ 2.16 (s, 6H, CH3), 2.54 (t, 8H, NCH2), 2.77 (t, 8H, NHCH2), 3.75 ((s, 8H, ArCH2), 7.19 (s, 8H, ArH). 13C NMR (100 MHz, CDCl3, TMS): 42.2 (NHCH2), 46.9 (CH3), 53.9 (NHCH2 ), 56.5 (NCH2), 128.2 (Ar-CH), 138.9 (Ar-C). Anal. Calcd for (C26H42N6): C, 71.19; H, 9.65; N, 19.16. Found: C, 71.53; H, 9.77; N, 19.31.
26. [H4L(Br)2](Br)2:C26H46N6Br4 M =762.33, crystal size 0.25 x 0.23 x 0.20 mm3, triclinic, PI, a = 5.7991 (5), b = 9.5238 (10), c = 14.7954 (14) Å, α = 74.360 (5)°, β = 84.001 (6)°, γ = 88.462 (6)°, V =782.58 (13)Å3, Z =1, dcalc = 1.618 gcm-3, T =90 K, F(000) = 384, μ(Mo-Kot) = 5.17 mm-1, 7513 independent reflections (33284 measured), R = 0.028, Rint = 0.023, wR(F2) = 0.068. Intensity data for the complex were collected using Nonius KappaCCD diffractometer, γ (MoKα) = 0.71073 A7ring;. The weighted R-factor wR and goodness of fit S are based on F2, conventional R-factors R are based on F, with Fset to zero for negative F2. The threshold expression of F2> σ(F2) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F. CCDC 742965.
27. Binding constants were obtained by 1H NMR (300 MHz Bruker) titrations of H4L(TsO)4 with NaCl in D2O at pH 2, and with n-(Bu)4NBr in CDCl3. Initial concentrations were [ligand]0 = 5 mM, and [anion]0 = 50 mM. In the case of D2O, sodium salt of 3-(trimethylsilyl)propionic-2,2,3,3,-d4 acid (TSP) in D2O was used as an external reference in a capillary tube. The pH was adjusted with a concentrated solution of TsOH and NaOH in D2O. Each titration was performed by twelve measurements at room temperature. The association constant K was calculated using Sigma Plot software, from the following equations: Aδ = ([A]0 + [L]0 + 1/K - (([A]0 + [L]0 + 1/K)2 - 4[L]0[A]0)1/2) Aδmax/ 2[L]0 (where L = ligand and A = chloride). Error limit in κ was less than 15%.
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