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  • Organic Chemistry  (19)
  • supramolecular chemistry  (8)
  • 1995-1999  (16)
  • 1975-1979  (11)
  • 1
    Electronic Resource
    Electronic Resource
    Double Subroutine Self-Assembly; Spontaneous Generation of a Nanocyclic Dodecanuclear Cu1 Inorganic Architecture (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 99-104 
    Details
    ISSN: 0947-6539
    Keywords: bipyridines ; copper compounds ; selfassembly ; supramolecular chemistry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The newly synthesised ligand 2 combines binding components known to undergo specific and distinct self-assembly processes with Cu1 ions. It complexes Cu1 to form, in almost quantitative yield, a large inorganic architecture 1 made up from four ligand molecules and twelve metal ions. The structure of 1 was ascertained by X-ray radiocrystallography as well as by NMR spectroscopy and electrospray mass spectrometry. It consists of a macrocycle of nanometric dimension with an external diameter of 28 Å; the central cavity has a diameter of 11 Å, which contains four PF-6 anions as well as solvent molecules. The spontaneous formation of 1 results from a self-assembly process based on a “program” combining two assembly subroutines, each specific to one of the ligand subunits. Self-assembly through double or, more generally, multiple subroutines can be used to generate a wide variety of highly complex inorganic supramolecular architectures by combination of two or more assembly processes.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030116
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  • 2
    Electronic Resource
    Electronic Resource
    Enthalpy and Entropy of Formation of Alkali and Alkaline-Earth Macrobicyclic Cryptate Complexes [1] (1976)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 59 (1976), S. 1099-1111 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The enthalpies and entropies of complexation of alkali and alkaline-earth metal cations by several macrobicyclic ligands have been obtained from calorimetric measurements and from the previously determined stability constants [2]. Both enthalpy and entropy changes play an important role in the stability and selectivity of the complexes. Particularly noteworthy are the large enthalpies and the negative entropies of complexation obtained for the alkali cation complexes (Na+, K+, Rb+ and Cs+ cryptates). The Sr2+ and Ba2+ as well as [Li+ ⊂ 2.1.1]For use of the symbols see [2].and [Na+ ⊂ 2.2.1] cryptates are of the enthalpy dominant type with also a favourable entropy change. The Ca2+ and [Li+ ⊂ 2.2.1] cryptates are entirely entropy stabilized with about zero heat of reaction. The high stability of the macrobicyclic complexes as compared to the macromonocylcic ones, the cryptate effect, is of enthalpic origin. The enthalpies of complexation display selectivity peaks, as do the stabilities, whereas the entropy changes do not. The high M2+/M+ selectivities found in terms of free energy, may be reversed when enthalpy is considered in view of the very different role played by the entropy term for M2+ and M+ cations. The enthalpies and entropies of ligation show that whereas the cryptate anions are similar in terms of entropy irrespective of which cation is included, the ligands, despite being more rigid than the hydration shell, are nevertheless able to adjust to some extent to the cation. This conclusion agrees with published X-rays data. The origin of the enthalpies and entropies of complexation is discussed in terms of structural features of the ligands and of solvation effects.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19760590414
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  • 3
    Electronic Resource
    Electronic Resource
    Cryptates XXIVPrevious paper see [1].: Structure and stability of mononuclear and binuclear cation inclusion complexes of cylindrical macrotricyclic ligands (1977)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 60 (1977), S. 141-151 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The cylindrical macrotricyclic ligands 1-3 yield inclusion complexes, [3]-cryptates, with various metal cations. NMR. studies indicate the successive formation of a mononuclear and a binuclear complex. The former is probably unsymmetrical undergoing fast intramolecular cation exchange; the latter is symmetrical, with a cation located on each macrocyclic subunit of the macrotricyclic system. A heteronuclear (Ag2+, Pb2+) complex has been observed. The stability constants of the mononuclear and binuclear alkali and alkaline-earth cation complexes of ligands 1-3 have been determined by potentiometric methods. The stabilities are comparable to those of the complexes of the isolated macrocyclic subunit 5b. The binuclear complexes are almost as stable as the mononuclear one even in highly charged species like for instance the complex of ligand 2 with two barium cations. Cylindrical macrotricyclic ligands are topologically well suited for the designed positioning of two metal cations in a binuclear inclusion complex.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19770600116
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  • 4
    Electronic Resource
    Electronic Resource
    Cryptates. XXV.Previous Publication see [1]. Stability and selectivity of cation inclusion complexes of polyaza-macrobicyclic ligands. Selective complexation of toxic heavy metal cations (1978)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 61 (1978), S. 67-82 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: We have measured the stability constants of the cryptate complexes formed by ligands 1-4 with alkali, alkaline-earth, transition metal and toxic heavy metal cations. Stabilities and selectivities of complexation of the alkali and alkaline-earth cations are less pronounced in 1-4 than in the parent compounds 5 and 6 and decrease as the number of nitrogen sites increase. Remarkable complexation properties are found towards transition metal and toxic heavy metal cations. The intramolecular cavity of ligands 1-3 is too large for small cations like Co2+, Ni2+, Zn2+ so that the complexes formed are comparatively weak; however these cations are strongly complexed by ligand 4 whose intramolecular cavity has a much smaller size, compatible with their ionic radius. On the other hand, ligands 1-4 all form highly stable cryptates with Cd2+, Hg2+, Pb2+. Thus by the combined operation of the two structural parameters, cavity size and nature of the binding sites, cryptands 2 et 3 present very high selectivities for the complexation of these toxic heavy metal cations with respect to the biologically important ones Na+, K+, Mg2+, Ca2+, Zn2+. The selectivities of ligand 2 for Cd2+, Hg2+ and Pb2+ with respect to Zn2+ are as high as 106, 1018 and 109 respectively. They are much more pronounced than those of previously known complexing agents. Cryptands like 2 and 3 thus present a unique selectivity sequence of special interest in detoxication (decorporation, depollution). Further structural elaboration may allow to design ligands which present a given selectivity pattern of potential use in “cryptatotherapy” and “environment pollution control”. The results also provide evidence for the existence, at low pH, of protonated complexes which probably participate in an acid catalysed process for dissociation of the complexes.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19780610107
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  • 5
    Electronic Resource
    Electronic Resource
    CRYPTATES XIXPublication précédente voir [1].. Ligands polyaza-polyoxa-macrobicycliques: Synthèse et complexes métalliquesDédié au Professeur H. H. Inhoffen à l'occasion de son 70° anniversaire (1976)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 59 (1976), S. 1566-1583 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Polyaza-polyoxa macrobicyclic ligands: its synthesis and metal complexes.The synthesis of the polyaza-polyoxa macrobicyclic ligands 1-4 is described. They form complexes with a variety of metal cations, transition metal cations as well as alkali and alkaline-earth cations. These complexes may be formulated as cation inclusion complexes, cryptates, in which the cation is contained in the intramolecular cavity. The properties of the complexes are described. An especially interesting feature is that these ligands, polymines of macrobicyclic topology, provide a means of trapping transition metal cations inside a molecular cavity; thus they impose coordination geometries and may modify the spectral and redox properties of the cations.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19760590516
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  • 6
    Electronic Resource
    Electronic Resource
    Stereoelectronic Properties, Stereospecificity and Stabilization of α-Seleno Carbanions. An ab initio StudyStereoelectronic Effects, Part 6; Part 5, see [2]. (1977)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 60 (1977), S. 1239-1246 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An ab initio study of α-seleno carbanions show that they are subject to appreciable polarization and stereoelectronic effects. Like in α-thia carbanions, the equatorial e forms are more stable than the axial a forms, one of the stabilizing contributions being the conformation dependent (C-lone pair, σ* Se—Z) interaction. The carbanion stabilizing effect of the α-Se atom is about 3 kcal/mol larger than that of the sulfur analog. As in the case of the sulfur no specific effect of the d orbitals is found.
    Additional Material: 4 Tab.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19770600413
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  • 7
    Electronic Resource
    Electronic Resource
    Coordination Arrays: Synthesis and Characterisation of Rack-Type Dinuclear Complexes (1996)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 2 (1996), S. 1292-1302 
    Details
    ISSN: 0947-6539
    Keywords: complexes with nitrogen ligands ; ruthenium complexes ; self-assembly ; supramolecular chemistry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A series of mono- and dimetallic complexes of rack type containing a dinucleating bis-tridentate ligand and RuII-2,2′:6′,2′-terpyridyl (tpy) sites were synthesised and characterised. The 1H NMR spectra of the dimetallic complexes were correlated to structural features, and the crystal structures of the dimetallic complexes were determined. They provide information about the way in which the central substitutent affects the overall shape of the racks and the relative disposition of the metal centres, measured by the pinching angle of the bis-tridentate ligand and the convergence angle of the ancillary tpy units. The latter demonstrates that a CH3 group yields the least bent complex and indicates how parallel the tpy units are. The dimetallic racks exhibit metal-metal interactions mediated by the bis-tridentate ligands as indicated by electrochemical and spectroscopic methods. The bridging-ligand π* orbital and the dπ metal orbital are stabilised by complexation of a second metal. The results obtained provide guidelines for the design of extended racks bearing several metal centres in a linear arrangement, which also represent potential components of molecular electronic devices.
    Additional Material: 14 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19960021017
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  • 8
    Electronic Resource
    Electronic Resource
    Cyclodextrin chemistry. Selective modification of all primary hydroxyl groups of α- and β-cyclodextrins (1978)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 61 (1978), S. 2190-2218 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two efficient methods are described for the selective modification of all six primary hydroxyl groups of α-cyclodextrin (α-CD, 11). One, using an indirect strategy, involves protection of all 18 hydroxyl functions as benzoate esters, followed by selective deprotection of the six primary alcohol groups. The other, using a direct strategy, involves selective activation of the primary hydroxyl groups via a bulky triphenylphosphonium salt, which is then substituted by azide anion as the reaction proceeds. A number of modified α-cyclodextrin derivatives have been prepared and fully characterized, among which are: the useful intermediate α-cyclodextrin-dodeca (2, 3) benzoate (3); hexakis (6-amino-6-deoxy)-α-cyclodextrin hexahydrochloride (7); hexakis (6-amino-6-deoxy)-dodeca (2, 3)-O-methyl-α-cyclodextrin hexahydrochloride (9), hexa (6)-O-methyl-α-cyclodextrin (13). The direct substitution is shown to be even more efficient for β-cyclodextrin (16), giving the heptakis (6-azido-6-deoxy)-β-CD-tetradeca (2, 3)acetate (17), while the indirect strategy fails. The compounds are characterized by extensive use of 13C- and 1H-NMR. spectroscopy. The steric and statistical problems of selective polysubstitution reactions for the cyclodextrins are discussed, and possible reasons for the observed differences in reactivity between α- and β-cyclodextrins are examined.The dodecabenzoate 3 presents a very marked solvent effect on physical properties (IR. and NMR. spectra, optical rotation); the effects observed may be ascribed to an unusually strong intramolecular network of hydrogen bonds which severely distorts the α-cyclodextrin ring and lowers the symmetry from six-fold to three-fold.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19780610622
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  • 9
    Electronic Resource
    Electronic Resource
    Synthesis and properties of chiral macrotricyclic ligands. Complexation and transport of chiral molecular cations and anionsPrevious paper, see [1]. (1978)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 61 (1978), S. 2407-2418 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The optically active macrotricyclic cryptands 1 and 2, containing the binaphthyl group as chiral unit, have been synthesized. These compounds contain lateral cavities which may serve as anchoring sites for polar groups of the substrates and a central, chiral cavity large enough for including more or les completely the bulk of a molecular ion. Their complexation properties towards molecular ions give evidence for the occurrence of two types of processes: (a) direct complexation of primary ammonium cations, like phenylethyl ammonium chloride, occurs with either 1 or 2; (b) cascade binding, involving first complexation of an alkali cation followed by pairing with a molecular anion, takes place with 2. Process (b) may be considered as a metallo-receptor model system where binding of an anionic substrate is dependent on initial binding of a cation. In both cases (a) and (b) weak resolution of chiral racemic substrates has been observed by extraction and transport (through a bulk liquid membrane) experiments. This indicates that in the complex the bulk of the substrate should be located close to the chiral unit and therefore more or less in the central cavity. In the case of cryptand 2, the resolution achieved for the (±)-mandelate anion is markedly affected by the nature of the complexed cation.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19780610713
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  • 10
    Electronic Resource
    Electronic Resource
    Anion Cryptates: Synthesis, Crystal Structures, and Complexation Constants of Fluoride and Chloride Inclusion Complexes of Polyammonium Macrobicyclic LigandsDedicated to the memory of Willy Simon (1996)
    New York, NY : Wiley-Blackwell
    Helvetica Chimica Acta 79 (1996), S. 569-587 
    Details
    ISSN: 0018-019X
    Keywords: Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Three macrobicyclic octamines 1-3 and the macrotricyclic hexadecamine 14 have been synthesized. The octamines 1-3 bind anionic substrates when protonated. The stability constants of the complexes between the protonated forms of the macrobicyclic polyamines and halide anions have been determined by pH-metric measurements. The stability constants in H2O are very high; 1 in its hexaprotonated form binds F- with high selectivity (selectivity F-/Cl- 〉 108), while 3 exhibits strong stability constants for both F- and Cl-. Three X-ray structures have been obtained, one where F- is held inside the cavity of 1 · 6H+, one where Cl- is included in 3 · 6H+, and 3 · 6H+ where the cavity is empty.
    Additional Material: 5 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/hlca.19960790302
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