Synthese von 6,7,8,9,15,16,17,18-Octahydrodibenzo[f,m][1,8,4,11]- dithiadiazacyclotetradecin-8,17-diessigsäure (H2L1); Strukturen entsprechender Kupfer-Komplexe

Funkemeier, Dieter; Mattes, R.

doi:10.1002/cber.19911240608

Cited by 9 publications

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References 18 publications

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“…Variation of pH within the range of 3-7 revealed a sharpening of reduction/oxidation peaks for Cu (II) (NSNS2A) as the pH decreased that was initially attributed to the protonation of the acetate arms. The presence of only subtle changes in the EPR and UV spectra at different pH (Table2; Fig.S16and Fig.S21in ESI) rules out any significant structural transformations around the copper ion upon anticipated protonation of acetate arms, in accord with the previously reported copper (II) complex with [14]-ane-[NSNS2Bz2A] 37. In the present case, in the calculated structure of [Cu (II) (H2NSNS2A)] 2+ with protonated acetate arms, the copper ion retains a square-planar [N2S2] coordination (Fig.9), whereas protonation weakens Cu-O bonds, leading to an elongation of the octahedron.…”

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Revisiting dithiadiaza macrocyclic chelators for copper-64 PET imaging

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“…. 37 In the present case, in the calculated structure of [Cu (II) (H2NSNS2A)] 2+ with protonated acetate arms, the copper ion retains a square-planar [N2S2] coordination (Fig. 9), whereas protonation weakens Cu-O bonds, leading to an elongation of the octahedron.…”

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Revisiting dithiadiaza macrocyclic chelators for copper-64 PET imaging

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“…1 740( 7) 2356( 7) 2520 (7) 2 160( 6) 1997( 5) 2980( 5) 3722( 6) 46 1 6( 6) 4769 ( 5) 3989( 5) 3300( 6) 3254( 5) 3798( 6) 3767 (7) 3 169( 6) 2625 (6) 106 I(4) -344(4) -894(4) -1617(5) -I795(6) -1254 (6) -530 (5) -20 ( 7) -724 (7) -939 (5) I679( 3) 1245( 3) 1497( 4) 1098( 4) 458( 4) 223 (4) 495 (4) 502 (5) -322(4) 766 ( 5) 15 16(6) 1985 (5) 1683(4) The aqueous phase was separated and eluted three times with CH,Cl, (30 cm3). The solvent was dried with Na,S04 and removed with a rotary evaporator to leave the product L2, 8) 4022 (9) 605( 9) 1737( 9) 1326( 3) 1298( 10) 245( 10) 2247 ( 10) 1569( 1 1) 26OO( 5) 3764( 16) 1866( 24 6) 3359( 6) 2790( 6) 3228( 6) 8997( 3) 9423( 8) 8927( 10) 9346( 7) 8253( 7) 5661( 3) 5539( 9) 5067( ...…”

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Synthesis and structural studies of copper(II), nickel(II) and cobalt(II) complexes of a 14-membered trans-N2S2 dibenzo macrocycle with two pendant pyridylmethyl groups

Funkemeier¹,

Mattes²

1993

J. Chem. Soc., Dalton Trans.

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The 8,17-bis(2-pyridylmethyI) -functionalised derivative ( Lz) of a 14-membered trans-N,S, dibenzo macrocycle 6,7,8,9,15,16,17,18-octahydrodibenzo[ f,m] E1.8.4.11 ]dithiadiazacyclotetradecine has been prepared and its crystal structure determined. The ligand Lz forms stable complexes with nickel(l1) 1, copper(ii) 2 and cobalt(i1) 3. The complexes have been isolated in the solid state and characterised by standard methods and single-crystal X-ray diffraction. Crystal data for L2: space group P2,lc. a = 945.6(1), b = 1467.9(2), c = 1041.1 (2) pm, p = 115.67(1)", Z = 2, R(R') = 0.035(0.040) for 2183 observed reflections. Complex 1: space group P2,/n, a = 1418.8(3), b = 1288.8(3).c = 1867.0(4) pm, p = 109.20(3)", Z = 4, R ( R ' ) = 0.067(0.068) for 4124 observed reflections. The nickel atom lies outside the macrocyclic cavity and is in a distorted octahedral cis-N,S, environment. Complex 2: space group P r , a = 787.8(2), b = 11 37.5(2), c = 1800.5(4) pm. z = 98.84(3), p = 99.43(3), y = 94.74(3)", Z = 2, R ( R ' ) = 0.082(0.075) for 2165 observed reflections. The copper atom exhibits a highly distorted trigonal-prismatic co-ordination geometry with the following distances: Cu-S, 242.7(4) and 269.8(4), Cu-N(amine) 225.8(11) and 255.2(10) and Cu-N(pyridine) 198.4(11) and 200.2(12) pm, respectively. Complex 3: space group P i , a = 789.3(2), b = 1165.8(2), c = 1806.2(3) pm, a = 98.90(1), p = 98.86(2), y = 94.24(2)", Z = 2, R(R') = 0.066(0.063) for 3039 observed reflections. The geometry about high-spin cobalt(ii) is trigonal prismatic with average Co-S, Co-N(amine) and Co-N (pyridine) bond lengths of 252.5, 229.0 and 213.7 pm, respectively. The stereochemistry of the free and complexed ligand is discussed

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Synthesis and Characterization of Copper(II) Complexes of a 14‐Membered cis‐N₂S₂ Dibenzo Macrocycle and of Its Bis‐acetato and Bis(methylpyridyl) Derivatives

1995

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The synthesis and characterization of seven copper coordina-hibit very similar overall structures in the cationic part. The tion compounds with the 14-membered macrocyclic cis-NzS2 macrocyclic ring of the ligand is folded along an N...S axis, dibenzo ligand 6,?,13,14,15,16,17,18-octahydrodibenzo[e,m]-the octahedral geometry is strongly Jahn-Teller distorted, L3.The structural, spectral, EPR, and electrochemical properties of these compounds will be compared with complexes described as possible models of N2S2 coordination environments at the active sites of "blue" copper(I1) proteins [*]. Results and DiscussionThe hexadentate ligands H2L2 and L3 were prepared in moderate yields by one-step reactions from the preformed macrocycle L1 and a-bromoacetic acid (H2L2) or 2-[@-tolylsulfonyl)methyl]pyridine (L3). According to the IR spectrum H2L2 exists in a zwitterionic state: one of the tertiary amine functions is protonated and one of the carboxyl groups deprotonated. The other carboxyl group forms a strong intermolecular hydrogen bond to the carboxylate group of a neighboring ligand molecule as is shown by the high background infrared absorption in the range from 1800 to 600 cm-' with a maximum at 1400The preparation of the copper(I1) complexes 1 and 3-7 was straightforward by using the appropriate inorganic components. All the complexes are stable in air and readily soluble in water. The copper(1) compound [CuL'IBr . MeCN (2) is air-sensitive.

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Synthese von 6,7,8,9,15,16,17,18-Octahydrodibenzo[f,m][1,8,4,11]- dithiadiazacyclotetradecin-8,17-diessigsäure (H2L1); Strukturen entsprechender Kupfer-Komplexe

Cited by 9 publications

References 18 publications

Revisiting dithiadiaza macrocyclic chelators for copper-64 PET imaging

Revisiting dithiadiaza macrocyclic chelators for copper-64 PET imaging

Synthesis and structural studies of copper(II), nickel(II) and cobalt(II) complexes of a 14-membered trans-N2S2 dibenzo macrocycle with two pendant pyridylmethyl groups

Synthesis and Characterization of Copper(II) Complexes of a 14‐Membered cis‐N₂S₂ Dibenzo Macrocycle and of Its Bis‐acetato and Bis(methylpyridyl) Derivatives

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Synthese von 6,7,8,9,15,16,17,18-Octahydrodibenzo[f,m][1,8,4,11]- dithiadiazacyclotetradecin-8,17-diessigsäure (H2L1); Strukturen entsprechender Kupfer-Komplexe

Cited by 9 publications

References 18 publications

Revisiting dithiadiaza macrocyclic chelators for copper-64 PET imaging

Revisiting dithiadiaza macrocyclic chelators for copper-64 PET imaging

Synthesis and structural studies of copper(II), nickel(II) and cobalt(II) complexes of a 14-membered trans-N2S2 dibenzo macrocycle with two pendant pyridylmethyl groups

Synthesis and Characterization of Copper(II) Complexes of a 14‐Membered cis‐N2S2 Dibenzo Macrocycle and of Its Bis‐acetato and Bis(methylpyridyl) Derivatives

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Synthesis and Characterization of Copper(II) Complexes of a 14‐Membered cis‐N₂S₂ Dibenzo Macrocycle and of Its Bis‐acetato and Bis(methylpyridyl) Derivatives