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  • 1
    Electronic Resource
    Electronic Resource
    Sulfonamide-based catenanes  -  regioselective template synthesisDedicated to Professor Hans Jürgen Bestman at the occasion of his 70th birthday. (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 1855-1860 
    Details
    ISSN: 0947-3440
    Keywords: Catenane synthesis ; Macrocycles ; Molecular recognition ; Sulfonamides ; Intertwining mechanism ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The first catenanes containing sulfonamide units were synthesized. Selective formation of the in/out isomer 7 can be explained by host-guest interactions that cause a regioselective templating effect. Replacement of O2S-NH by O2S-NMe increases the yield significantly (from 10 to 19%). The sulfonamide catenane 7 has a topologically chiral structure.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199510260
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  • 2
    Electronic Resource
    Electronic Resource
    Non-Ionic Template Synthesis of Amide-Linked Rotaxanes: Olefinic and Aliphatic Axle Building Blocks (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 2269-2273 
    Details
    ISSN: 0947-3440
    Keywords: Association constant ; Mechanical bonding ; Molecular recognition ; Template synthesis ; Supramolecular chemistry ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: The first synthesis of amide-linked rotaxanes with non-arene axle building blocks is reported. The threading synthesis of rotaxane 8 with olefinic fumaryl chloride proves that arene moieties are not necessary for non-ionic template syntheses. Mass spectroscopic evidence of a rotaxane bearing an aliphatic axle, derived from succinic acid, revealed that hydrogen bonding, rather than π,π interactions, is the predominant template binding force. 1H-NMR titration studies on the threading synthesis of these mechanically bonded molecules were carried out. The association constants measured suggest that the incorporation of the corresponding monoamide monochloride (cf. 7), rather than the incorporation of the diacid dichloride (cf. 5), plays the key role in these rotaxane syntheses. The X-ray structural analysis of a semi axle (14) reveals hydrogen bonding patterns characteristic of diamides.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719971114
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  • 3
    Electronic Resource
    Electronic Resource
    Amide-Based [3]Catenanes and [2]Catenanes with Aliphatic Chains (2000)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 2000 (2000), S. 499-505 
    Details
    ISSN: 1434-193X
    Keywords: Catenanes ; Molecular recognition ; Template effect ; Mechanical bond ; Key-lock interaction ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: ---[3]Catenanes of the amide type were synthesized preparatively for the first time. Large macrocycles bearing two guest-binding sites were used to synthesize these amide-linked [3]catenanes in yields of 4%, either by formation of rigid macrocyclic boxes, or with macrocycles consisting of flexible long-chained aliphatic diamines. Furthermore, the systematic introduction of 1,ω-alkane diamines as building blocks for catenanes is described. The synthesis of a series of [2]catenanes by varying the ring size of one of the two macrocycles was also achieved in yields of 10%.
    Additional Material: 7 Ill.
    Type of Medium: Electronic Resource
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  • 4
    Electronic Resource
    Electronic Resource
    Chiral Amide Rotaxanes with Glucose Stoppers - Synthesis, Chiroptical Properties and Wheel-Axle Interactions (1998)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1998 (1998), S. 2003-2007 
    Details
    ISSN: 1434-193X
    Keywords: Supramolecular chemistry ; Rotaxanes ; Mechanical bond ; Molecular recognition ; Chirality ; Chemistry ; General Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: In this paper we report on amide rotaxanes with tetrabenzoylglucose stoppers. When acetyl groups are used instead of benzoyl groups, merely a pseudo-rotaxane 5 is obtained. The circular dichroism measurements of the rotaxanes 6a and 6b differ significantly from that one of the free axle 7. Similarly, the Cotton effects of the mixtures of achiral wheels 2a and 2b and chiral axle indicate intermolecular host-guest interactions, likewise. After an addition of a solution of NaOMe the wheel is slipping off immediately and quantitatively by hydrolysis, as the benzoylglucose stoppers decrease in size by hydrolysis.
    Type of Medium: Electronic Resource
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  • 5
    Electronic Resource
    Electronic Resource
    Chiral Pyridinophanes as Hydrogen-Bonding Supramolecular Building Blocks (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 1221-1225 
    Details
    ISSN: 0947-3440
    Keywords: Aggregations ; Circular dichroism ; Cyclophanes ; Molecular recognition ; Supramolecular chemistry ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Hydrogen-donor and hydrogen-acceptor substituted chiral cyclophanes with a [2](1,3)benzeno[2](3,5)pyridinophane framework have been synthesized, enantiomerically separated, and analysed by circular dichroism (CD). X-ray structure determination and CD analyses show that these cyclophanes are able to act as hydrogen-bonding donor/acceptor building blocks for the design of chiral supramolecular aggregates with suitable complementary partners. Starting from the pyridinophane N-oxide 4, selective reactions lead to the new chiral pyridinophanes 5-7 in high yields. The X-ray structure analysis of the pyridinophane-2-carbonitrile 5 reveals a multilayered herringbone structure as it forms dimeric aggregates. The CD analysis of the host 7 with the complementary guest molecules melamine and cyanuric acid elucidates the formation of supramolecular complexes in solution.
    Additional Material: 4 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719970626
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