J. Reedijk
Leiden University, LIC, Emeritus
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ABSTRACT The new ligand 1,6-bis(3,5-dimethyl-1-pyrazolyl)-2,5-dithiahexane (bddh) rendered the following coordination compounds with copper(I) and copper(II) salts: Cu(bddh)(NO3)2, [Cu(bddh)(H2O)](BF4)2, [Cu(bddh)Cl]2CuCl4,... more
ABSTRACT The new ligand 1,6-bis(3,5-dimethyl-1-pyrazolyl)-2,5-dithiahexane (bddh) rendered the following coordination compounds with copper(I) and copper(II) salts: Cu(bddh)(NO3)2, [Cu(bddh)(H2O)](BF4)2, [Cu(bddh)Cl]2CuCl4, [Cu(bddh)(Hdmpz)](BF4)2 (Hdmpz=3,5-dimethylpyrazole), [Cu(bddh)Cl]BF4, [Cu(bddh)]2(BF4)2, Cu(bddh)Cl and Cu(bddh)Br. The compound [Cu(bddh)Cl]2CuCl4 crystallizes from ethanol in the monoclinic space group Cc, with a=19.018(4), b=14.840(3), c=14.963(3) Å, β=100.24(2), V=4158 Åp3, Z=4 and Dcalc=1.63 g cm−3. The refinement using 5145 measured and 1826 observed (F>2σ(F)) reflections resulted in the R values 0.062 (R) and 0.068 (Rw). The asymmetric unit consists of two [Cu(bddh)Cl]+ cations and a CuCl42− anion. The copper(II) atom in [Cu(bddh)Cl]+ cation is coordinated by two pyrazole nitrogen atoms in trans position (1.991(9) and 1.98(1) Å), two thioether atoms in cis position (2.422(3) and 2.480(3) Å) and one chloride atom (2.249(4) Å) in a distorted trigonal bipyramid with the nitrogen donors on axial positions and the two sulfurs and chloride in the equatorial plane. The tetrahedral CuCl42− anion lies in disorder. The compound [Cu(bddh)(Hdmpz)](BF4)2 crystallizes from ethanol in the monoclinic space group P21/c, with a=18.360(3), b=9.419(3), c=16.068(2) Å, β= 100.29(1), V=2734 Å3, Z=4 and Dcalc=1.55 g cm−3. The refinement using 6883 measured and 2326 observed (F>2σ(F)) reflections resulted in the R values 0.055 (R) and 0.061 (Rw). The asymmetric unit consists of a [Cu(bddh)(Hdmpz)]2+ cation and two tetrafluoroborate anions. The copper(II) atom is coordinated by three pyrazole nitrogen atoms (1.987(6) and 1.962(6) Å; Hdmpz: 1.977(6) Å) and two sulfur atoms (2.478(2) and 2.404(3) Å) in a distorted trigonal bipyramid, with the ligand pyrazole groups on axial positions. The copper(I) compound [Cu(bddh)]2(BF4)2 crystallizes from ethanol in the monoclinic space group C2/c, with a=22.679(2), b=12.766(2), c=14.213(2) Å, β=106.69(1), V=3942 Å3, Z=8 and Dcalc=1.55 g cm−3. The refinement using 1495 observed (F>2.5σ(F)) reflections resulted in the R values 0.049 (R) and 0.082 (Rw). The cationic part of the compound is dinuclear with C2 symmetry. The copper(I) ions are 4.603(3) Å apart. Each copper(I) ion is coordinated by a pyrazole nitrogen atom at 2.067(6) Å and two thioether atoms at 2.426(2) and 2.333(3) Å from one ligand and by a pyrazole nitrogen at 1.980(8) Å of another ligand in a strongly distorted tetrahedral fashion. Spectroscopic results strongly suggest that the compounds [Cu(bddh)(H2O)](BF4)2 and [Cu(bddh)Cl]BF4 contain the trigonal bipyramidal [Cu(bddh)A] unit (A=anion), as present in [Cu(bddh)Cl]2CuCl4 and [Cu(bddh)(Hdmpz)](BF4)2. The compounds Cu(bddh)Cl and Cu(bddh)Br are IR and X-ray isomorphous.
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... J. Reedijk, WL Driessen and WL Groeneveld Rec. Trav. Chim. Pays-Bas 88 (1969), p. 1095. J. Reedijk, PWNM van Leeuwen and WL Groeneveld Recl. Trav. Chim. Pays-Bas 87 (1968), p. 129. JWFM Schoonhoven, WL Driessen, J. Reedijk and GC... more
... J. Reedijk, WL Driessen and WL Groeneveld Rec. Trav. Chim. Pays-Bas 88 (1969), p. 1095. J. Reedijk, PWNM van Leeuwen and WL Groeneveld Recl. Trav. Chim. Pays-Bas 87 (1968), p. 129. JWFM Schoonhoven, WL Driessen, J. Reedijk and GC Verschoor J. Chem. ...
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... G. Haasnoot, Dick de Vos, § and Jan Reedijk* . ... Binding of Antitumor Ruthenium Complexes to DNA and Proteins: A Theoretical Approach. Neva Beker, Cecilia Coletti, Alessandro Marrone, and Nazzareno Re. The Journal of Physical... more
... G. Haasnoot, Dick de Vos, § and Jan Reedijk* . ... Binding of Antitumor Ruthenium Complexes to DNA and Proteins: A Theoretical Approach. Neva Beker, Cecilia Coletti, Alessandro Marrone, and Nazzareno Re. The Journal of Physical Chemistry B 2007 111 (33), 9955-9964. ...
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The phenol‐based ligand Hpy2ald containing formyl, amine and pyridine functions reacts with copper(II) nitrate, copper(II) bromide and manganese(II) chloride to yield complexes with unexpected structures. In contrast to previously... more
The phenol‐based ligand Hpy2ald containing formyl, amine and pyridine functions reacts with copper(II) nitrate, copper(II) bromide and manganese(II) chloride to yield complexes with unexpected structures. In contrast to previously reported coordination compounds with similar ligands, the carbonyl group of the ligand in all complexes does not coordinate to the metal ions. The metal‐to‐ligand ratio is 2:1 in the case of the copper(II) nitrate complex and 1:1 in the case of the copper(II) bromide and manganese(II) chloride complexes. The copper(II) nitrate complex exhibits both donor‐atom and coordination number asymmetry, as one copper ion is pentacoordinate with an N3O2 donor set, and the other one is hexacoordinate with an O6 donor set. In the latter two complexes, the phenol group of the ligand remains protonated and fails to bridge the two metal ions; instead it is semi‐coordinated to only one metal ion. This results in the formation of mononuclear complexes in which copper(II) or...
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An unprecedented 1D ladder coordination polymer based on a pentanuclear copper(ii) 2,4,6-tris(dipyridin-2-ylamino)-1,3,5-triazine building blockElectronic supplementary information (ESI) available: additional characterization data for 1 (µeff vs. T and B curves), TGA, XRD. See http://www.rsc.org/...more
Copper(II) nitrate reacts with the rigid polydentate triple-connecting dpyatriz ligand in acetonitrile to an unprecedented infinite molecular ladder in which five-coordinated copper pseudo-dimer are bridged by nitrate anions and the... more
Copper(II) nitrate reacts with the rigid polydentate triple-connecting dpyatriz ligand in acetonitrile to an unprecedented infinite molecular ladder in which five-coordinated copper pseudo-dimer are bridged by nitrate anions and the coordination polymer chains are linked by hexacoordinated copper ions leading to the formation of large guest cavities.
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N-(3-methoxypropyl)-N-(pyridin-2-ylmethyl)amine (abbreviated as mppma) and its complex [Mn(μ-Cl)2(mppma)]n have been synthesized. Single-crystal X-ray diffraction analysis has revealed that in the complex, mppma acts as a didentate ligand... more
N-(3-methoxypropyl)-N-(pyridin-2-ylmethyl)amine (abbreviated as mppma) and its complex [Mn(μ-Cl)2(mppma)]n have been synthesized. Single-crystal X-ray diffraction analysis has revealed that in the complex, mppma acts as a didentate ligand bound to the Mn(II) ion through two nitrogen atoms; [MnCl2(mppma)] units are connected by double chloride bridges to form one-dimensional zigzag chains of edge-sharing distorted MnCl4(mppma) octahedra. The temperature-dependent magnetic susceptibility data have been explained with Fisher model, with parameters J=−0.25 cm−1 and g=1.99, indicating weak antiferromagnetic coupling.
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ABSTRACT Co-ordination compounds of the new ligand 1,8-bis(3,5-dimethyl-1 -pyrazolyl)-3,6-dithiaoctane (bddo) with MCl2(M = Fe, Mn, Ni, Co, Zn, Cu, or Cd), MBr2(M = Mn, Co, Ni, or Zn), Cu(BF4)2, and CuX (X = BF4, NCS, Cl, Br, or I) are... more
ABSTRACT Co-ordination compounds of the new ligand 1,8-bis(3,5-dimethyl-1 -pyrazolyl)-3,6-dithiaoctane (bddo) with MCl2(M = Fe, Mn, Ni, Co, Zn, Cu, or Cd), MBr2(M = Mn, Co, Ni, or Zn), Cu(BF4)2, and CuX (X = BF4, NCS, Cl, Br, or I) are described. The general formula for the divalent metal is [M(bddo)X2] and for copper(I), [Cu2(bddo)X2]. With CuCl2 two modifications were obtained. The green modification of [Cu(bddo)Cl2] crystallises in space group P21/n with a= 9.019(2), b= 28.671(5), c= 8.431(2)Å, β= 113.65(2)°, R= 0.055, and R′= 0.066 for 1 578 unique reflections [I > 2σ(I)]. The compound consists of Cu(bddo)Cl2 units. The copper atom is co-ordinated by two pyrazole nitrogens and two chloride atoms, in trans positions, in a distorted square-planar geometry. The red modification of [Cu(bddo)Cl2] crystallises in space group Pbcn with a= 9.397(4), b= 15.093(4), c= 15.142(4)Å, Z= 4, R= 0.069, and R′= 0.089 for 864 unique reflections [I > σ(I)]. This compound consists of CuCl2 units linked together by ligand molecules, thus forming chains with distinct C2 symmetry perpendicular to the chain axis. The copper atom is co-ordinated in a distorted-tetrahedral geometry by two pyrazole nitrogens and two chloride atoms in cis positions. The sulphur atoms do not participate in the co-ordination, although molecular-mechanics calculations show that the ligand bddo is not sterically hindered to form tetradentate mononuclear chelates, i.e. with a MN2S2 chromophore. The structures of the other divalent metal halides were established as being very similar to that of the red modification. For [Cu(bddo)(BF4)2] semi-co-ordination of one or both tetrafluoroborates is indicated by the i.r. spectrum. Solid-state 13C n.m.r. spectra of the copper(I) compounds indicate that the S atoms show significant shifts, suggesting co-ordination. In the thiocyanate and iodide compounds both thioether sulphurs co-ordinate in an identical manner, whereas in the chloride and bromide compounds they co-ordinate in a different manner.
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Four different-anion Ag(I) compounds with the ligand norharmane (9H-Pyrido[3,4-b]indole; Hnor) and having the general formula [Ag(Hnor)2](anion) (anion=ClO4(-), NO3(-) and BF4(-)) [Ag(Hnor)2(MeCN)](PF6) are reported, and studied in detail... more
Four different-anion Ag(I) compounds with the ligand norharmane (9H-Pyrido[3,4-b]indole; Hnor) and having the general formula [Ag(Hnor)2](anion) (anion=ClO4(-), NO3(-) and BF4(-)) [Ag(Hnor)2(MeCN)](PF6) are reported, and studied in detail regarding their coordination mode and in vitro antiproliferative effects. X-ray structural analysis revealed that the complex with the PF6(-) anion has a MeCN solvent molecule weakly coordinated to Ag(I), making the metal coordination T-shaped, while the other compounds present the classical linear Ag(I) coordination. The compounds showed certain cell growth inhibitory effects in two different cancer cell lines, with the perchlorate containing complex being the most toxic and in fact comparable to cisplatin. Notably, the compounds are stable in visible light; and the luminescence in the solid state was found to be extremely weak, whereas in MeOH solution all compounds show a moderate to weak emission band at 375 nm, when excited at 290 nm.
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Chemistry, Inorganic Chemistry, Medicine, Single crystal x-ray diffraction, Humans, and 15 moreCyanide, Silver, Perchlorate, Light, Luminescence, X ray diffraction, Complexes, Inorganic Biochemistry, Cell Proliferation, Harmine, Ligands, Linear Geometry, proton magnetic resonance spectroscopy, Silver sulfadiazine, and lung neoplasms
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Abstract Four tetradentate nitrogen donor ligands have been prepared by condensation of N-hydroxymethylpyrazoles with ethylenediamines. These ligands are varied by methylation of the pyrazole rings (edbd) or the aminonitrogens (debp), or... more
Abstract Four tetradentate nitrogen donor ligands have been prepared by condensation of N-hydroxymethylpyrazoles with ethylenediamines. These ligands are varied by methylation of the pyrazole rings (edbd) or the aminonitrogens (debp), or both (debd). Copper(II) complexes of the type CuL(ClO4)2 have been isolated with L = debp, edbp, edbd. For L = debd, the adducts salts Cu(debd)(dMp)X2, with X = ClO4−, BF4− and dMp = 3,5-dimethylpyrazole, were obtained. The compounds were characterized by their absorption (d-d) and EPR spectra. All four undergo quasi-reversible electrochemical reduction in methanol, the redox potentials being correlated with the degree of ligand methylation. The copper(I) forms are relatively unstable, and also bind carbon monoxide with different affinities.
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The syntheses and characterizations are described of 18 transition metal coordination compounds with the novel tridentate ligand N,N-bis(2-ethyl-5-methyl-imidazol-4-ylmethyl)-aminopropane (biap). Compounds with formulae... more
The syntheses and characterizations are described of 18 transition metal coordination compounds with the novel tridentate ligand N,N-bis(2-ethyl-5-methyl-imidazol-4-ylmethyl)-aminopropane (biap). Compounds with formulae [M(biap)(X)(Y)(H2O)n]·(solvent) with X−, Y−=Cl−, Br−, NO3−, CH3COO− and NCS−, and n=0 or 1, and [M(biap)2](BF4)2·(solvent), with M=Co2+, Ni2+, and Zn2+, as well as the dinuclear complexes [Ni(biap)X2]2 (X−=Cl−, NCS−) have been isolated. The ligand biap acts as a
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The selective production of aldehydes from primary alcohols is a very important chemical transformation of organic synthesis, since a wide variety of fine chemicals possess this carbonyl function.1,2 Various effective methods have been... more
The selective production of aldehydes from primary alcohols is a very important chemical transformation of organic synthesis, since a wide variety of fine chemicals possess this carbonyl function.1,2 Various effective methods have been developed to perform this oxidation reaction.3,4 For ...
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Engineering, Condensed Matter Physics, Chemistry, Inorganic Chemistry, Crystallography, and 15 moreApplied Physics, Inorganic, Magnetic field, Crystal structure, Copper, Magnetic Properties, Chromium, Iron Oxide, Iron, High Temperature, Ac Susceptibility, Magnetic Anisotropy, Chemical Composition, Antiferromagnetism, and Copper Complex
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ABSTRACT Three new copper(II) compounds are described containing chelating bis(imidazole)-based ligands. Compound 1, [Cu2(L1)2(H2O)2][SiF6]2·10H2O, was obtained by reaction of [bis-(1H-imidazol-2-yl)-methyl]-pyridin-2-ylmethyl-amine (L1)... more
ABSTRACT Three new copper(II) compounds are described containing chelating bis(imidazole)-based ligands. Compound 1, [Cu2(L1)2(H2O)2][SiF6]2·10H2O, was obtained by reaction of [bis-(1H-imidazol-2-yl)-methyl]-pyridin-2-ylmethyl-amine (L1) with Cu(BF4)2·6H2O in a glass vessel for a few weeks. The single-crystal X-ray structure of 1 consists of dinuclear copper(II) units, formed through ligand sharing. The starting BF4− anion was replaced by the SiF62− in the crystal structure of 1. In the crystal lattice, a discrete (H2O)8cluster forms an eight-membered ring and is linked through four shared water molecules with the other (H2O)8cluster. Both waterclusters show hydrogen-bonding interactions with the neighbouring SiF62− anion. To investigate the effect of the presence of a bridging ligand such as oxalate on the coordination chemistry of L1 and copper(II) ion, compound 2, [Cu2(L1)(H2O)2][Cu(C2O4)2(ClO4)2]·2H2O, was prepared by reaction of L1 and Cu(ClO4)2·6H2O in the presence of oxalic acid; the crystal structure is built from 4+ and 4− ions in the crystal lattice. Compound 3, [Cu(ClO4)(C2O4)(HL2)H2O]·2H2O, was formed from the reaction of ligand [bis-(1H-imidazol-2-yl)-methyl]-isopropyl-amine (L2) and Cu(ClO4)2·6H2O in the presence of oxalic acid. The isopropylaminegroup is not coordinated to the copper in this case, but protonated. In compound 3, a mononuclear copper(II) unit is present, built from a bidentate L2, a bidentate oxalate, a monodentate perchlorate and a water. Two copper coordination entities are doubly bridged through hydrogen bonds with twice the pathway [Cu–OC2O4–(Owater)–Cu] to form a dimeric-like species. Low-temperature magnetic susceptibility studies showed no interaction between copper(II) ions.
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The catalytic activity of {[Fe(mebpa)Cl]2O}(ClO4)2 (1) (mebpa = N-(2-methoxyethyl)-N,N-bis(pyridin-2-yl-methyl)amine) with H2O2 for the functionalization of alkanes and alkenes has been investigated. The experimental results show that... more
The catalytic activity of {[Fe(mebpa)Cl]2O}(ClO4)2 (1) (mebpa = N-(2-methoxyethyl)-N,N-bis(pyridin-2-yl-methyl)amine) with H2O2 for the functionalization of alkanes and alkenes has been investigated. The experimental results show that compound 1 is stable during the catalytic cycle and it is an efficient catalyst for cyclohexane oxidation leading to an alcohol:ketone ratio of 3.5. Compound 1 is also found to be an active and selective catalyst for the epoxidation of alkenes. In all cases, the catalytic efficiency is strongly dependent on the presence of additives and the reaction conditions.
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Chemistry, Inorganic Chemistry, Kinetics, DNA damage, Medicine, and 15 moreDNA, Copper, Biological, Cisplatin, High Resolution, Mode of action, DNA Cleavage, Gel electrophoresis, Organometallic Compounds, Binding Site, Oligonucleotides, Biochemistry and cell biology, Molecular Structure, DNA fragmentation, and Copper Complex
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Abstract Two different solid complexes were obtained from the same starting materials in solution, i.e. a six- coordinate complex, [Cu(bidhx)Cl2], and, in the presence of some extra water, a five-coordinate complex, [Cu(bidhx)Cl]Cl(H2O)2.... more
Abstract Two different solid complexes were obtained from the same starting materials in solution, i.e. a six- coordinate complex, [Cu(bidhx)Cl2], and, in the presence of some extra water, a five-coordinate complex, [Cu(bidhx)Cl]Cl(H2O)2. These solid complexes have been previously characterized, by chemical analyses, X-ray structure, and spectroscopic properties. Their cyclovoltammetric behaviour and solution spectra in dimethyl sulfoxide are now described. It was found that two waves were observed in the case of the six-coordinate complex, but only one for the five-coordinate. It was also found that these waves were quite dependent on the nature of the supporting electrolyte, on addition of extra chloride ion and on addition of water. A possible interpretation of these experimental results is presented and compared with earlier obtained results. Under these experimental conditions the redox potentials of [Cu(bidhx)Cl2] and [Cu(bidhx)Cl]Cl(H2O)2 are about +0.26 and −0.02 V versus SCE (+0.50 and +0.22 V versus NHE) respectively. The first value is close to those found for the blue copper proteins.
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Synthesis and spectroscopic studies on transition-metal nitrates and thiocyanates of a chelating imidazole-thioether ligand. The crystal structures of diaquabis[5-methyl-4-(ethyl-mercaptomethyl)imidazole]nickel(II) dinitrate, diaquabis[5-methyl-4-(ethyl-mercaptomethyl)imidazole] copper(II) dinitr...more
Abstract The synthesis and characterization of some monomeric transition-metal coordination compounds with the novel bidentate ligand 5-methyl-4-(ethyl- mercaptomethyl)imidazole (abbreviated memi) are described, viz.... more
Abstract The synthesis and characterization of some monomeric transition-metal coordination compounds with the novel bidentate ligand 5-methyl-4-(ethyl- mercaptomethyl)imidazole (abbreviated memi) are described, viz. [M(memi)2(H2O)2](NO3)2 and M(memi)2(NCS)2 with M = Co, Ni, Cu. Single crystals of [Ni(memi)2(H2O)2](NO3)2 (A), [Cu(memi)2(H2O)2](NO3)2 (B) and Co(memi)2(NCS)2 (C) were used in structure determinations. The three compounds all crystallize in the monoclinic space group P21/n with Z = 2. The cell dimensions for compound A are a = 10.402(2), b = 13.589(4), c = 8.476(3) A, β = 108.35(2)°, V = 1137.21 A3 and Dx = 1.551 g cm−3. The cell dimensions of compound B are a = 10.451(3), b = 13.430(5), c = 8.757(4) A, β = 109.24(3)°, V = 1160.35 A3 and Dx = 1.53 g cm−3. The cell dimensions for compound C are a = 12.147(7), b = 9.096(4), c = 10.363(4) A, β = 102.14(4)°, V = 1119.27 A3, and Dx = 1.447 g cm−3. The structures were solved by heavy-atom techniques and refined by least-squares methods to residual Rw values of 0.032 (A), 0.033 (B) and 0.046 (C). The coordination geometry of the metal ion in all compounds is distorted octahedral. In compounds A and B the metal ion is lying on a centre of symmetry and is surrounded by two thioether sulfur atoms, two imidazole nitrogen atoms and two oxygen atoms from water molecules. In contrast to the nickel ion in structure A the copper ion in compound B has a significantly elongated octahedral geometry in the direction of the oxygen molecules. The compound with the much stronger coordinating anion, NCS (compound C) resembles the structures of A and B in having the same coordination geometry with the thiocyanate anions coordinating instead of the water molecules.
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... 14. J. Reedijk, PWNM van Leeuwen and WL Groeneveld. Recl. Trav. Chim. Pays-Bas 87 (1968), p. 129. 15. K. Nakamoto. (3rd edn. ... 19. J. Reedijk, WL Driessen and WL Groeneveld. Recl. Trav. Chim. Pays-Bas 88 (1969), p. 1095. 20. ABP... more
... 14. J. Reedijk, PWNM van Leeuwen and WL Groeneveld. Recl. Trav. Chim. Pays-Bas 87 (1968), p. 129. 15. K. Nakamoto. (3rd edn. ... 19. J. Reedijk, WL Driessen and WL Groeneveld. Recl. Trav. Chim. Pays-Bas 88 (1969), p. 1095. 20. ABP Lever. ...
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ABSTRACT Detailed iron-S7 M6ssbauer spectroscopy studies of the 2- and 3-CH 3substituted versions of the title ligand have been performed. For the 2-CH 3compound there is no evidence of spin crossover behavior. However, their spectra... more
ABSTRACT Detailed iron-S7 M6ssbauer spectroscopy studies of the 2- and 3-CH 3substituted versions of the title ligand have been performed. For the 2-CH 3compound there is no evidence of spin crossover behavior. However, their spectra suggest the possibilities of complex combinations of (a) essentially static fractions of facial and meridional high spin Fe(ll) isomers; (b) only one st~uctur~l isomer (facial or meridional) but a static fraction of orbital singlet (~A or B) ground state high spin form along with a single ~E high spin fraction that in turn undergoes a reversible transformation to two high spin 5E ground term forms on decreasing the temperature below -250 K. The latter behavior is probably the consequence of order-disorder involving the counter-anion. Depending on the nature of the solvent and specific type of the counter-anion, the 3-CH 3- derivatives exhibit varying degrees of resolution of: ~ultiple high spin forms at ambient temperature and conversion to the low spin ~A ground state. For the 2- and 3-CH 3substituted ligands there is the possibility of N-I as well as N-4 triazole coordination, to further complicate matters. Figure I. 2 r f
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Support from the Graduate Research School Combination “Catalysis” and the European Cooperation in the Field of Science and Technology (COST) program Action D35/0011, the Spanish Consejo Superior de Investigaciones Cientificas (CSIC), as... more
Support from the Graduate Research School Combination “Catalysis” and the European Cooperation in the Field of Science and Technology (COST) program Action D35/0011, the Spanish Consejo Superior de Investigaciones Cientificas (CSIC), as well as from the Spanish Ministerio de Ciencia y Innovacion, for access to BM16 at the European synchrotron radiation facility (ESRF) through grant number 16-01-723, are acknowledged. The Advanced Light Source is supported by the Director, Office of Science, Office of Basic Energy Sciences, of the U.S. Department of Energy under Contract No. DE-AC02-05CH11231.