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  • 1
    Electronic Resource
    Electronic Resource
    Catenated Cyclodextrins (1995)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 1 (1995), S. 33-55 
    Details
    ISSN: 0947-6539
    Keywords: catenanes ; cyclodextrins ; macrocycles ; orientational isomerism ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A novel synthetic approach is described for the construction of catenanes in aqueous solution from a partially methylated cyclodextrin (CD)-namely, heptakis(2,6-di-O-methyl-β-cyclodextrin) (DM-β-CD)-and a range of substrate molecules that contain a hydrophobic central core in the form of a 4,4′-disubstituted biphenyl unit (usually bitolyl) carrying two hydrophilic polyether side chains terminated by primary amine functions. In water, the amphiphilic catenane precursors form 1:1 complexes with β-CD and DM-β-CD and 2:1 (guest: host) complexes with the larger γ-CD. Macrocyclizations of the biphenyl-containing substrates with aromatic diacid chlorides in aqueous solution and in the presence of DM-β-CD under Schotten-Baumann conditions afforded-in low yields-a range of [2]- and [3]catenanes. When a consitutionally asymmetrical diamine was employed as the substrate, orientational isomers of a [2]catenane were obtained. A [3]catenene incorporating a macrocyclic tetralactam was found to exist as a mixture of head-to-head and head-to-tail isomers, which could be separated by high pressure liquid chromatography and identified unambiguously by nuclear magnetic resonance spectroscopy. One of the [2]catenanes afforded good single crystals from which the solid state structure was determined by X-ray crystallography. Other techniques which aided the characterization of these novel compounds included ultraviolet/visible and luminescence spectroscopy, dynamic nuclear magnetic resonance spectroscopy and fast atom bombardment mass spectrometry. Generally speaking, the catenated cyclodextrins are soluble in halogenated and aromatic hydrocarbons as well as in hydroxylic solvents. The existence of these new compounds gives us a unique insight into the nature of the noncovalent bonding interactions that cyclodextrins employ in binding substrate molecules.
    Additional Material: 29 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19950010109
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  • 2
    Electronic Resource
    Electronic Resource
    Pseudorotaxanes formed between secondary dialkylammonium salts and crown ethers“Molecular Meccano”, Part 6: for Part 5, see ref. [45e]. (1996)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 2 (1996), S. 709-728 
    Details
    ISSN: 0947-6539
    Keywords: crown ethers ; dialkylammonium salts ; hydrogen bonding ; molecular recognition ; pseudorotaxanes ; self-assembly ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A very simple self-assembling system, which produces inclusion complexes with pseudorotaxane geometries, is described. The self-assembly of eight pseudorotaxanes with a range of stoichiometries-1:1, 1:2, 2:1, and 2:2 (host:guest)-has been achieved. These pseudorotaxanes self-assemble from readily available components-well-known crown ethers, such as dibenzo[24]crown-8 and bis-p-phenylene[34]crown-10, and secondary dialkylammonium hexafluorophosphate salts, such as (PhCH2)2NH+2PF-6 and (nBu)2NH+2PF-6-and have been characterized not only in the solid state, but also in solution and in the “gas phase”. The pseudorotaxanes are stabilized largely by hydrogen-bonding interactions and, in some instances, by aryl-aryl interactions.
    Additional Material: 40 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.1460020614
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  • 3
    Electronic Resource
    Electronic Resource
    Synthetic Cyclic Oligosaccharides-Syntheses and Structural Properties of a Cyclo[(1 → 4)-α-L-rhamnopyranosyl-(1 → 4)-α-D-mannopyranosyl]trioside and -tetraosideSynthetic Cyclic Oligosaccharides, Part 1. (1996)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 2 (1996), S. 580-591 
    Details
    ISSN: 0947-6539
    Keywords: carbohydrates ; cyclodextrin analogues ; cyclooligomerizations ; glycosylations ; nanotubes ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: An efficient polycondensation-cyclization approach to the synthesis of cyclodextrin analogues is demonstrated by the preparation of cyclohexaoside 1 and cyclooctaoside 2. The key intermediate, disaccharide 3, bearing the cyanoethylidene group as a glycosyl donor function and the trityloxy group as a glycosyl acceptor function was prepared in 15 steps starting from L-rhamnose and D-mannose. The crucial cyclooligomerization of the disaccharide monomer 3 was carried out in the presence of TrClO4 as a promoter with the use of ultra-dry conditions at normal concentrations. This reaction led to formation of the cyclic oligosaccharides 28 and 29 (in 34 and 31% yield, respectively), which were deprotected to afford 1 and 2, respectively. The X-ray crystal structural analysis of the cyclooctaoside 2 reveals a cylindrical shape for the cyclic oligosaccharide with C4 symmetry. Individual molecules of 2 are arranged perfectly in stacks that form nanotubes in the solid state.
    Additional Material: 14 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19960020518
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  • 4
    Electronic Resource
    Electronic Resource
    Self-assembling [2]- and [3]rotaxanes from secondary dialkylammonium salts and crown ethersMolecular Meccano, Part 7: for Part 6; see the preceding paper in this issue (ref. [14]). (1996)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 2 (1996), S. 729-736 
    Details
    ISSN: 0947-6539
    Keywords: interlocking moleucles ; molecular recognition ; pseudorotaxanes ; rotaxanes ; template syntheses ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The self-assembly of three new rotaxanes - two [2]rotaxanes and a [3]rotaxane - formed by a “threading followed by stoppering” approach is described. These template-directed syntheses rely on the formation of pseudorotaxane intermediates, which self-assemble in solution from functionalized secondary dialkylammonium hexafluorophosphate threads and macrocyclic polyether rings (either dibenzo-[24]crown-8 or its asymmetric constitutional isomer). The stoppers - substituted 1,2,3-triazoles-were created by thermally allowed 1,3-dipolar cycloadditions between azido groups, which terminate the threads, and di-tert-butyl acetylenedicarboxylate.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.1460020615
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  • 5
    Electronic Resource
    Electronic Resource
    Simple Mechanical Molecular and Supramolecular Machines: Photochemical and Electrochemical Control of Switching Processes“Molecular Meccano”, Part 14: for Part 13, see D. B. Amabilino, P. R. Ashton, V. Balzani, C. L. Brown, A. Credi, J. M. J. Fréchet, J. W. Leon, F. M. Raymo, N. Spencer, J. F. Stoddart, M. Venturi, J. Am. Chem. Soc., in press. (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 152-170 
    Details
    ISSN: 0947-6539
    Keywords: luminescence ; photochemistry ; redox chemistry ; self-assembly ; self-complexation ; template syntheses ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Photochemical control of a self-assembled supramolecular 1:1 pseudorotaxane (formed between a tetracationic cyclophane, namely the tetrachloride salt of cyclobis(paraquat-p-phenylene), and 1,5-bis[2-(2-(2-hydroxy)ethoxy)ethoxy]naphthalene) has been achieved in aqueous solution. The photochemical one-electron reduction of the cyclophane to the radical trication weakens the noncovalent bonding interactions between the cyclophane and the naphthalene guest - π-π interactions between the π-electron-rich and π-electron-poor aromatic systems, and hydrogen-bonding interactions between the acidic α-bipyridinium hydrogen atoms of the cyclophane and the polyether oxygen atoms of the naphthalene derivative - sufficiently to allow the guest to dethread from the cavity; the process can be monitored by the appearance of naphthalene fluorescence. The radical tricationic cyclophane can be oxidized back to the tetracation in the dark by allowing oxygen gas into the system. This reversible process is marked by the disappearance of naphthalene fluorescence as the molecule is recomplexed by the tetracationic cyclophane. This supramolecular system can be chemically modified such that the π-electron-rich unit, either a naphthalene derivative or a hydroquinone ring, and the tetracationic cyclophane are covalently linked. We have demonstrated that the π-electron-rich residue in this system is totally “self-complexed” by the cyclophane to which it is covalently attached. Additionally, the self-complexation can be switched “off” and “on” by electrochemical two-electron reductions and oxidations, respectively, of the tetracationic cyclophane component. Thus, we have achieved the construction of two switches at the nanoscale level, one driven by photons and the other by electrons.
    Additional Material: 15 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030123
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  • 6
    Electronic Resource
    Electronic Resource
    A Novel Type of Isomerism in [3]CatenanesMolecular meccano, part 20; for part 19, see: M. Asakawa, P. R. Ashton, W. Dehaen, G. L'abbé, S. Menzer, J. Nouwen, F. M. Raymo, J. F. Stoddart, M. S. Tolley, S. Toppet, A. J. P. White, D. J. Williams, Chem. Eur. J. 1997, 3, 772. (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 788-798 
    Details
    ISSN: 0947-6539
    Keywords: catenanes ; dynamics ; isomerization ; NMR spectroscopy ; self-assembly ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The self-assembly of three [3]-catenanes based on a single tetracationic cyclophane - cyclobis(bipyridinium-1,4-di-ethoxybenzene) - with pairs of identical interlocked crown ethers - bis-p-phenyl-ene[34]crown-10, bis-1,5-dioxynaphthal-ene[38]crown-10, or tetrafluoro-p-phenyl-ene-p-phenylene[34]crown-10 - has been achieved in yields of 34, 31, and 33%, respectively. The solid-state structures of these [3]catenanes, determined by X-ray crystallography, are consistent with molecules having approximately C2h symmetry. In the solution state, the π-electron rich aromatic ring systems of the crown ether components, residing within the cavity of the tetracationic cyclophane, can adopt two different relative orientations, thus giving rise to two distinct isomeric forms possessing either C2h or D2 symmetries. Two dynamic processes have been characterized in the [3]catenane incorporating bis-1,5-dioxynaphthalene[38]-crown-10 macrocycles, by means of variable-temperature 1H NMR spectroscopy and subsequent lineshape analyses. The slower process is the exchange between C2h and D2 isomers, and the faster process is the rotation of the bipyridinium units of the cyclophane around their N=N axes. The evaluation of the free energies of activation at 298 K, which are, for the slower process, ca. 16 kcal mol-1, and for the faster one, ca. 14.5 kcal mol-1, has enabled us to propose a scenario in which the two included 1,5-dioxynaphthalene ring systems move continuously about the center of the cavity of the tetracationic cyclophane. A partial dissociation of one 1,5-dioxynaphthalene ring system allows the adjacent bipyridinium units to rotate about their long axes, whereas a complete dissociation is presumably necessary to allow a 1,5-dioxynaphthalene ring system to rotate about its O=O axis. The isomerism between the C2h and the D2 isomers of the [3]catenane incorporating the two bis-1,5-dioxynaphthalene[38]crown-10 rings is dependent upon 1) translational motions between the two crown ether rings and the central tetracationic cyclophane and 2) conformational changes within at least one of the two crown ether rings.
    Additional Material: 12 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030519
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  • 7
    Electronic Resource
    Electronic Resource
    Bis[2]catenanes and a bis[2]rotaxane-Model Compounds for Polymers with Mechanically Interlocked Components“Molecular Meccano”, Part 5: for Part 4, see P. R. Ashton, R. Ballardini, V. Balzani, A. Credi, M. T. Gandolfi, S. Menzer, L. Pérez-Garcia, L. Prodi, J. F. Stoddart, M. Venturi, A. J. P. White, D. J. Williams, J. Am. Chem. Soc. 995, 117, 11171-11197. (1996)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 2 (1996), S. 31-44 
    Details
    ISSN: 0947-6539
    Keywords: catenanes ; polycatenanes ; polyrotaxanes ; rotaxanes ; self-assembly ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The self-assembly of three bis[2]catenanes and a bis[2]rotaxane, by two complementary strategies, is reported. A synthetic route to derivatives of bis-para-phenylene[34]crown-10 (BPP34C10) and 1,5-naphtho-para-phenylene[36]-crown-10 (1/5NPP36C10) containing a fused five-membered ring with a secondary amine function is described. These intermediate N-allylimido macrocyclic polyethers undergo template-directed reactions with 1,1′-[1,4-phenylenebis-(methylene)]bis-4,4′-bipyridinium bis-(hexafluorophosphate) and 1,4-bis(bromo-methyl)benzene to produce [2]catenanes containing an N-allyl functionality. The N-allylimido macrocyclic polyethers have also been reduced and deprotected to afford macrocycles possessing a free NH group, which are then linked through a 4,4′-biphenyldicarbonyl spacer to produce bis(crown ether)s, in which each crown ether moiety has two recognition sites. These ditopic BPP34C10 and 1/5NPP36C10 derivatives are capable of sustaining self-assembly reactions at both recognition sites to yield bis[2]catenanes. The self-assembly of a complementary bis[2]catenane, in which two tetracationic cyclophanes are linked together with a flexible hexyl chain, has also been achieved by treating 1,1′-[1,4-phenylenebis(methylene)]bis-4,4′-bipyridinium bis-(hexafluorophosphate) with a compound containing two linked 1,4-bis(bromomethyl)benzene units in the presence of BPP34C10. Replacing BPP34C10 with a dumbbell-shaped compound containing a linear polyether unit intercepted by a naphthalene residue and terminated by two bulky adamantoyl groups has led to the self-assembly of a bis[2]rotaxane. The X-ray crystal structures of one of the catenanes and its associated crown ether component are reported, together with solution state dynamic 1H NMR spectroscopic studies, showing that there is substantial degree of order characterizing the molecular structure of the catenanes.
    Additional Material: 10 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19960020109
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  • 8
    Electronic Resource
    Electronic Resource
    Toward Controllable Molecular Shuttles“Molecular Meccano”, Part 10: For part 9 see P. R. Ashton, R. Ballardini, V. Balzani, M. Belohradsky, M. T. Gandolfi, D. Philp, L. Prodi, F. M. Raymo, M. V. Reddington, N. Spencer, J. F. Stoddart, M. Venturi, D. J. Williams, J. Am. Chem. Soc. 1996, 118, 4931-4951. (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 1113-1135 
    Details
    ISSN: 0947-6539
    Keywords: molecular devices ; nanostructures ; rotaxanes ; self-assembly ; translational isomerism ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A number of nanometer-scale molecular assemblies, based on rotaxane-type structures, have been synthesized by means of a template-directed strategy from simple building blocks that, on account of the molecular recognition arising from the noncovalent interactions between them, are able to self-assemble into potential molecular abacuses. In all the cases investigated, the π-electron-deficient tetracationic cyclophane cyclobis(paraquat-p-phenylene) is constrained mechanically around a dumbbell-shaped component consisting of a linear polyether chain intercepted by at least two, if not three, π-electron-rich units and terminated at each end by blocking groups or stoppers. The development of an approach toward constructing these molecular abacuses, in which the tetracationic cyclophane is able to shuttle back and forth with respect to the dumbbell-shaped component, begins with the self-assembly of a [2]rotaxane consisting of two hydroquinone rings symmetrically positioned within a polyether chain terminated by triisopropylsilyl ether blocking groups. In this first so-called molecular shuttle, the tetracationic cyclophane oscillates in a degenerate fashion between the two π-electron-rich hydroquinone rings. Replacement of one of the hydroquinone rings - or the insertion of another π-electron-rich ring system between the two hydroquinine rings - introduces the possibility of translational isomerism, a phenomenon that arises because of the different relative positions and populations of the tetracationic cyclophane with respect to the π-donor sites on the dumbbell-shaped component. In two subsequent [2]rotaxanes, one of the hydroquinone rings in the dumbbell-shaped component is replaced, first by a p-xylyl and then by an indole unit. Finally, a tetrathiafulvalene (TTF) unit is positioned between two hydroquinone rings in the dumbbell-shaped component. Spectroscopic and electrochemical investigations carried out on these first-generation molecular shuttles show that they could be developed as molecular switches.
    Additional Material: 19 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030719
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  • 9
    Electronic Resource
    Electronic Resource
    Molecular and Supramolecular Synthesis with Dibenzofuran-Containing SystemsMolecular meccano, part 18; for Part 17, see D. B. Amabilino, P. R. Ashton, S. E. Boyd, M. Gómez-López, W. Hayes, J. F. J. Org. Chem. 1997, 62, 3062-3075. (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 1136-1150 
    Details
    ISSN: 0947-6539
    Keywords: crystal engineering ; dibenzofuran ; molecular quadrilaterals ; supra-molecular chemistry ; template synthesis ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The template-directed syntheses of two new tetracationic cyclophanes, cyclobis(paraquat-2,8-dibenzofuran) and cyclobis(paraquat-3,7-dibenzofuran), incorporating dibenzofuran subunits has been accomplished. Initially, the cyclophanes were self-assembled around a macrocyclic polyether template, bis-p-phenylene[34]crown-10 (BPP34C10), to form catenanes: the mechanical bond order of the catenane formed determined the requisite “amacrocyclic” templates for synthesis of the free cyclophane. X-ray crystallography shows that both of the cyclophanes possess rectangular covalent frameworks. Furthermore, these cyclophanes form self-assembled tapes in the solid state, since the dibenzofuran moieties have a tendency to associate with each other through crossed ∞-∞ stacks. The dibenzofuran-containing catenanes also form two-dimensional supramolecular arrays in the solid state on account of extended ∞-∞ stacking interactions. In addition, the serendipitous discovery of a plerotopic tecton (consisting of a dibenzofuran nucleus covalently linked from the 2- and 8-positions by methylene groups to 4,4′-pyridylpyridinium (hydrogen bond acceptor) and protonated bipyridinium (hydrogen bond donor) units) has been made. The tecton dimerizes in the solid state to form a supramolecular macrocycle, since its complementary hydrogen bonding sites are oriented in a horseshoelike fashion by the 2,8-disubstituted dibenzofuran unit. However, this superstructure is not retained in the 1:1 complex of the tecton with BPP34C10: cocrystallization of the tecton with this crown ether opens the macrocyclic two-component supermolecule to afford a hydrogen-bonded pseudopolyrotaxane.
    Additional Material: 15 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030720
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  • 10
    Electronic Resource
    Electronic Resource
    Achiral Cyclodextrin AnaloguesPart 2 of a series on synthetic cyclic oligosaccharides. For Part 1, see: P. R. Ashton, C. L. Brown, S. Menzer, S. A. Nepogodiev, J. F. Stoddart, D. J. Williams, Chem. Eur. J. 1996, 2, 580-591. (1997)
    Weinheim : Wiley-Blackwell
    Chemistry - A European Journal 3 (1997), S. 1299-1314 
    Details
    ISSN: 0947-6539
    Keywords: carbohydrates ; cyclodextrin analogues ; cyclooligomerizations ; glycosylations ; nanostructures ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The synthesis of a new family of cyclodextrin (CD) analogues is described. This family consists of novel cyclic oligosaccharides built from monosaccharides that possess the same relative but opposite absolute (D- and L-) configurations. The alternation of such D- and L- residues - specifically, D- and L-rhamnose or D- and L-mannose - in a macrocyclic structure results in Sn-type symmetry and, consequently, optical inactivity. The synthesis of these cyclic oligosaccharides was achieved by an economical polycondensation/cycloglycosylation approach that relies on an appropriately-derivatized disac-charide monomer and that avoids the time-consuming, and often low-yielding, stepwise growth of long linear oligosaccharide precursors. In the cases reported, the key precursors are the disaccharide monomers 1-RR and 1-MM, which bear both a glycosyl donor (cyanoethylidene function) and a glycosyl acceptor (trity-loxy group). These compounds are able to undergo Tr+-catalyzed polycondensation which, under appropriate dilution conditions, can be terminated by cycloglycosyl-ation. Thus, compound 1-RR was converted into a range of protected cyclic rhamnooligosaccharides 15-19 in 64% overall yield. All these products, including the unique cyclic dodeca- and tetradecasaccharides 18 and 19, have been isolated by preparative HPLC. Unexpectedly, treatment of the manno analogue of the disaccharide 1-RR (compound 1-MM) under the same conditions produced only the cyclic hexasaccharide 28 and numerous apparently linear oligomers. Removal of the protecting groups from 16-19 afforded the free cyclic oligosaccharides 21-24, which exhibited the predicted zero optical rotation and very simple NMR spectra, indicating highly symmetrical structures. X-ray crystallography reveals that in the solid state the cyclooctaoside 21 possesses a C2 symmetric structure, on account of a slight deformation of its cylindrical shape. The channel-type crystal packing of molecules of 21 forms nanotubes with an internal diameter of around 1 nm. Conversely, the cyclic hexasaccharide 29 possesses a Ci symmetric solid-state structure and its molecules pack to form a parquet-like superstructure.
    Additional Material: 18 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/chem.19970030818
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