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  • General Chemistry  (37)
  • Inorganic Chemistry  (11)
  • Radical pairs  (2)
  • 1
    Electronic Resource
    Electronic Resource
    Intramolecular Electron Transfer between 2,5-Dimethoxy-1,4-phenylene Units in [n.n]Paracyclophane Radical Cations (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 139-148 
    Details
    ISSN: 1434-193X
    Keywords: Paracyclophanes ; Cyclic voltammetry ; Radical cations ; ESR/ENDOR spectroscopy ; Intramolecular electron transfer ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: A range of [n.n]paracyclophane radical cations (4·+-12·+), in which two 2,5-dimethoxy-1,4-phenylene units are connected by alkano bridges of varying length, have been studied by ESR and ENDOR spectroscopy. In the [2.2]- and [3.3]paracyclophane radical cations 4·+-6·+, 10·+ and 11·+ the delocalization of the unpaired electron over both π-moieties and the distinct difference between the first and second oxidation potentials, ΔE = E20 - E10, are evidence for a strong intramolecular electronic interaction between the two electrophores. The [5.5] and [7.7] species (8·+ and 9·+) are localized radical cations at low temperature (ca. 220 K). At room temperature, the higher molecular flexibility leads to a significant increase in the number of internal collisions between the electrophores, resulting in a fast (ESR time scale) intramolecular electron transfer. The intermediate [4.4]paracyclophane radical cations 7·+ and 12·+ are apparently also localized radical cations. The close interplanar distance between the two π-moieties, however, facilitates their mutual contacts. In 7·+, the intramolecular electron transfer becomes fast on the ESR time scale at room temperature; in 12·+ the transfer is fast over the temperature range 200-300 K.
    Type of Medium: Electronic Resource
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  • 2
    Electronic Resource
    Electronic Resource
    On the Homoconjugation of Two Acceptor Groups (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 1615-1623 
    Details
    ISSN: 1434-193X
    Keywords: Homoconjugation ; Cyclovoltammetry ; ESR spectroscopy ; Diketones ; Heterocycles ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Cyclovoltammetric investigations have been carried out on 3,3,6,6-tetramethylcyclohexane-1,2,4,5-tetrone (4), bicyclo-[3.2.2]nonane-6,7,8,9-tetrone (5), and several of their congeners, such as 6,13-dihydro-6,6,13,13-tetramethylquin-oxalino[2.3-b]phenazine (13), 5,10-dihydro-5,5,10,10-tetra-methylpyrazino[2,3-g]quinoxaline (17), and 6,13-dihydro-6,13-propanoquinoxalino[2,3-b]phenazine (20). For 5 and 20 a large difference (ΔE° ≥400 mV) between the first and second reduction potentials was found. The ESR results of the radical anion 20•- are in support of a strong homoconjugation. ESR studies of 4•-, 13•-, and 17•- also reveal a symmetrical displacement of the unpaired electron over both acceptor groups on the ESR time scale which, however, based on the small potential difference ΔE° ≤ 200 mV can be most likely described to a fast electron exchange.
    Type of Medium: Electronic Resource
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  • 3
    Electronic Resource
    Electronic Resource
    Isomeric Tetrakis(dimethylamino)naphthalenes: Syntheses, Structure-Dependence of Basicities, Crystal Structures, and Physical Properties (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 1617-1622 
    Details
    ISSN: 1434-193X
    Keywords: Tetrakis(dimethylamino)naphthalenes ; Basicity ; Hydrogen bonds ; Cyclicvoltammetry ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---For comparison to the recently described 2,3,6,7-tetrakis(dimethylamino)naphthalene (1) the three isomers 2,3, and 4 were synthesized. The basicities of this group of isomers are strongly dependent upon the different mutual orientations of the pairs of dimethylamino substituents: only the isomers 3 and, partially, 4, both with dimethylamino groups in adjacent peri-positions of the naphthalene, are strong “proton sponges”. For the isomers 1 and 2 with the same number and kind of twofold dimethylamino substituents in neighbouring ortho-positions, however, no significant basicity increase is observed. To explain this difference between the two groups of isomers it is suggested that in the ortho-pairs of 1 and 2 the C-N bonds diverge considerably, leading to an increased N···N distance and consequently to less stable [N···H···N]+ hydrogen bonds in contrast to the parallel C-N bonds in the peri-substituted isomers 3 and 4. X-ray crystal structure analyses of the bases and of some of the salts derived therefrom were solved and are discussed. Cyclic voltammetry indicates that 1 to 4 are strong electron donors, reacting easily to radical cations or dications which with suitable acids have been obtained as salts.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Structural Characterization and Magnetic Behaviour of the Ferro-Antiferromagnetic Alternating Manganese-Azido Chain [Mn(3-Et,4-Mepy)2(μ-N3)2]n (3-Et,4-Mepy = 3-Ethyl-4-methylpyridine) (1999)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 1999 (1999), S. 687-691 
    Details
    ISSN: 1434-1948
    Keywords: Bridging ligands ; Manganese ; Azido bridge ; Alternating chain ; Magnetic properties ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The ligands 3-ethyl-4-methylpyridine (3-Et,4-Mepy) and azide coordinate to MnII forming an alternating chain with the formula [Mn(3-Et,4-Mepy)2(μ-N3)2]n. This compound crystallizes in the space group P-1. The compound consists of chains of octahedrally coordinated manganese atoms alternately bridged by double end-to-end (μ1,3) and double end-on (μ1,1) azido bridges, which results in a structurally and magnetically alternating chain. The 3-ethyl-4-methylpyridine ligands are arranged trans, completing the six-fold coordination spheres of the manganese atoms. The Mn-Mn distances are distinctly different: Mn(1)-Mn(1A) = 5.149(3) Å (double end-to-end azido bridge) and Mn(1)-Mn(1B) = 3.402(2) Å (double end-on azido bridge). The magnetic properties of the compound, as studied in the temperature range 300-4 K, show bulk antiferromagnetic interaction. Fitting of the magnetic data by using an equation for alternating ferro-antiferromagnetic S = 5/2 1-D systems gives the parameters JAF = -13.7(1) cm-1, JF = 2.4(1) cm-1, g = 2.036(2).
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    [2.2]Paracyclophane-4,7,12,15-tetrone, [2.2](1,4)Naphthalenophane-4,7,14,17-tetrone, and 1,4,8,11-Pentacenetetrone Radical Anions - A Comparative ESR Study (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 221-227 
    Details
    ISSN: 1434-193X
    Keywords: 1,4-Benzoquinones ; [2.2]Paracyclophanes ; 1,4,8,11-Pentacenetetrones ; Cyclic voltammetry ; Radical anions ; ESR/ENDOR spectroscopy ; Intramolecular electron transfer ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Three types of tetrone radical anions in which two 1,4-benzoquinone units are connected by ethano (1·-, 2·-), [2.2]paracyclophane (3·-, 4·-), and anthracene bridges (5·-, 6·-) have been studied by ESR and ENDOR spectroscopy. The displacement of the unpaired electron over the two π moieties in the [2.2]cyclophane radical anions 1·--4·- and the marked difference between the first and second reduction potentials, ΔE = |E20 - E10| ≥ 0.20 V, are evidence for a substantial intramolecular electronic interaction between the two electrophores. Similar ΔE data for the syn- (3) and anti-naphthalenophanes (4) indicate that most of the intramolecular electronic interaction takes place through the [2.2]paracyclophane bridge. When ion pairing is inhibited by complexation of the cation, the unpaired electron in 5·- and 6·- is also delocalized over the whole pentacenetetrone system at temperatures as low as 160 K.
    Type of Medium: Electronic Resource
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  • 6
    Electronic Resource
    Electronic Resource
    Intramolecular Electron Transfer between Terminal 1,4-Dimethoxybenzene Units in Radical Cations with a [2.2](1,4)Naphthalenophane, [2.2](1,4)Anthracenophane, and Pentacene Skeleton (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 1161-1170 
    Details
    ISSN: 1434-193X
    Keywords: [2.2](1,4)Naphthalenophanes ; [2.2](1,4)Anthracenophane ; Pentacene ; Cyclic voltammetry ; Radical cations ; ESR/ENDOR spectroscopy ; Intramolecular electron transfer ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Various radical cations, in which two terminal 1,4-dimethoxybenzene units are anellated to [2.2]paracyclophane (2b•+, 3b•+), [2.2](1,4)naphthalenophane (4d•+), and anthracene bridges (5•+), have been studied by ESR and ENDOR spectroscopy. In the syn- and anti-naphthalenophane radical cations 2b•+ and 3b•+ the delocalization of the unpaired electron over both π-moieties and the distinct difference between the first and second oxidation potentials, ΔE = E20 - E10, are evidence for a substantial intramolecular electronic interaction between the two electrophores. Extension of the bridge in 4d•+ and 5 by benzo anellation results in a localized radical cation. Strong intramolecular electronic interaction between the two electrophores is found in the 1,4,8,11-tetramethoxy-pentacene radical cation (5•+). The syntheses of 4d are described.
    Type of Medium: Electronic Resource
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  • 7
    Electronic Resource
    Electronic Resource
    2,3-Diphenyl-2,3-diazabicyclo[2.2.2]octan (1979)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 112 (1979), S. 1076-1079 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: 2,3-Diphenyl-2,3-diazabicyclo[2.2.2]octaneThe title compound 5 was synthesized by twofold arylation of 2,3-diazabicyclo[2.2.2]oct-2-ene (1). The conformational features of 5 are discussed using 1H NMR and PE data.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19791120332
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  • 8
    Electronic Resource
    Electronic Resource
    Phenazin-5(10H)-yls, 5Part 4: Ref[1].. - Intermolecular π-π Interactions (Pimerization) of tert-Butyl-Substituted Phenazin-5(10H)-yl Radicals in The Solid State: Syntheses, Crystal Structures and Magnetic Susceptibility Measurements (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 473-483 
    Details
    ISSN: 0947-3440
    Keywords: Phenazin-5(10H)-yl ; ESR spectroscopy ; Radical pairs ; π Interactions ; Dimer absorption ; Magnetic susceptibility ; Nitrogen heterocycles ; Radicals ; Magnetic properties ; Solid-state chemistry ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Introduction of tert-butyl groups into the phenazine frame-work was accomplished by treatment of 5-acetyl-5,10-dihydrophenazine (2a) with tert-butyl chloride in the presence of AlCl3. Starting from the 2,8- or 3,7-di-tert-butyl-substituted derivatives 2c and 2b, a series of phenazin-5(10H)-yl radicals (1c-i) was synthesized and characterized by ESR and EN-DOR spectroscopy. With the exception of 1c, all phenazin-5(10H)-yls were obtained in crystalline form, and for 1d-f the long-wavelength absorption band at λ ≈ 870 nm indicates intermolecular π-π interactions in the solid state. For 1d, 1e and 1h the crystal structure could be determined. The unit cell of 1d consists of eight phenazin-5(10H)-yls. Surprisingly, four of them are arranged in radical pairs, whereas the other four lie independently in the lattice. In agreement with this structure, the magnetic susceptibility results correspond to a content of 50% monoradical and an almost complete spinpairing in the radical pairs up to T = 220 K. In 1e, the four phenazin-5(10H)-yls in the unit cell are arranged in two independent radical pairs, A and B, which are characterized by close interplanar distances and short intermolecular contacts between atoms with significant spin populations. Accordingly, the susceptibility data indicate strong spin-pairing at low temperature. Due to extensive steric shielding of the phenazin-5(10H)-yl framework, the crystal structure of 1h gives no evidence of any π-π interactions between adjacent radicals. As expected, the magnetic susceptibility of 1h corresponds to that of an ordinary monoradical.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970307
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  • 9
    Electronic Resource
    Electronic Resource
    Phenazin-5(10H)-yls, 4Parts 1-3: Ref.. 10-Ethylphenazin-5(10H)-yl · H2O: Crystal Structure, Magnetic Susceptibility and Intermolecular π-π Interactions (Pimerization)Dedicated to Professor Rolf Gleiter on the occasion of his 60th birthday. (1996)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1996 (1996), S. 1867-1870 
    Details
    ISSN: 0947-3440
    Keywords: Phenazin-5(10H)-yl radicals ; Radical pairs ; π-π-Interactions ; Pimerization ; Dimer absorption ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The unit cell of 10-ethylphenazin-5(10H)yl · H2O consists of eight phenazin-5(10H)-yls that are arranged in four independent radical pairs A-D. All pairs show close interplanar distances (3.28-3.36 Å). Furthermore, A, B, and D are characterized by short intermolecular contacts between atoms with significant spin populations. This is not valid for the pair C with the closest interplanar distance of 3.28 Å. Magnetic susceptibility measurements as a function of temperature indicate complete spin pairing (“pimerization”) between 20 and 100 K. Therefore, the radical pair C provides evidence that unspecific close interplanar contacts together with a reasonable overlap of the π systems are sufficient to lead to pimerization.
    Additional Material: 3 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199619961121
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  • 10
    Electronic Resource
    Electronic Resource
    Verdazyls, 27. 1,1′,5,5′-Tetraphenyl-3,3′-biverdazyl, the Primary Bisverdazyl (1980)
    Weinheim : Wiley-Blackwell
    Berichte der deutschen chemischen Gesellschaft 113 (1980), S. 2049-2051 
    Details
    ISSN: 0009-2940
    Keywords: Chemistry ; Inorganic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Verdazyle, 27. 1,1′,5,5′-Tetraphenyl-3,3′-biverdazyl, das primäre BisverdazylDie Titelverbindung 3 wurde dargestellt. Die gefundenen Nullfeldaufspaltungsparameter |D′| = 305 G und |E′| ≍ 0 G entsprechen der Struktur.
    Additional Material: 1 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/cber.19801130543
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