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  • 1
    Electronic Resource
    Electronic Resource
    Crystal and molecular structure of 2-[(hydroxyimino)(methylthio)methyl]-1-methylpyridinium chloride, C8H11N2OS+ Cl− (1990)
    Springer
    Journal of chemical crystallography 20 (1990), S. 397-401 
    Details
    ISSN: 1572-8854
    Source: Springer Online Journal Archives 1860-2000
    Topics: Geosciences , Physics
    Notes: Abstract The X-ray structure analysis for single crystals of 2-[(hydroxyimino)(methylthio)methyl]-1-methylpyridinium chloride has been carried out, with finalR factor 0.029 in space groupP21/c. TheS-methyl substituted oxime group has theE configuration. The orientation of the oxime moiety in respect to the pyridinium, defined by N-C-C-N torsion angle, isgauche. The conformation of the title compound is similar to that of 2-[(hydroxyimino)(phenylthio)rnethyl]-1-methylpyridinium, but differs from that of 2-(hydroxyiminomethyl)-1-methylpyridinium which is highly active as the acetylcholinesterase reactivator. Molecular mechanics calculations and comparative conformational study of these three compounds suggest that the coplanarity of the oxime and pyridinium moieties is important for the antidotal activity in the nerve tissue, while the activity in blood does not seem to be related to the conformation observed in the crystalline state.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1007/BF01180103
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  • 2
    Electronic Resource
    Electronic Resource
    Synthesis, Solvatochromism, and Molecular Structure of a New Pyridinium N+N- Betaine Dye (1997)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1997 (1997), S. 2607-2611 
    Details
    ISSN: 0947-3440
    Keywords: Aminide salts ; Betaines ; Crystal structure ; Dyes ; Solvatochromism ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: Two methods for the synthesis of N-[4-(2,4,6-triphenyl-1-pyridinio)phenyl]-p-toluenesulfonaminide (4), a new betaine dye with positive and negative charges at two nitrogen atoms separated by an aromatic ring, are described. 4 displays a negative solvatochromic effect slightly smaller than that observed for the standard betaine 1 [ET(30) scale]. X-ray structure determination of crystals containing 4 and acetone solvate molecules in the molar ratio of 1:1 revealed that the geometry of the pyridinium moiety is strongly influenced by the negatively charged aminide nitrogen atom.
    Additional Material: 2 Ill.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.199719971228
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  • 3
    Electronic Resource
    Electronic Resource
    Unexpected reaction of 4-(2,4,6-triphenylpyridinio)phenolate with urea in aqueous solution  -  structure of 1-(4-hydroxyphenyl)-2,4,6-triphenylpyridinium cyanate (1995)
    Weinheim : Wiley-Blackwell
    Liebigs Annalen 1995 (1995), S. 2049-2051 
    Details
    ISSN: 0947-3440
    Keywords: Betaine dye ; Urea ; Pyridinium salt ; Cyanate ; Chemistry ; Organic Chemistry
    Source: Wiley InterScience Backfile Collection 1832-2000
    Topics: Chemistry and Pharmacology
    Notes: During crystallization of the pyridinium N-phenolate dye 1 from a saturated aqueous solution of urea, 1-(4-hydroxyphenyl)-2,4,6-triphenylpyridinium cyanate (4) is formed unexpectedly as verified by IR, 1H-NMR and X-ray structural analysis. Such a course of reaction can be explained by the strong nucleophilic character of the betaine dye 1. The anion of 4, [NCO]-, is disordered between two positions; one of them can be assigned to an isocyanate and the other to a cyanate group. The nitrogen atom of the anion is involved in an intermolecular, nearly linear hydrogen bond with the hydroxy group of the cation whereas its oxygen atom is pointing towards the pyridinium ring of an adjacent pyridinium cation.
    Type of Medium: Electronic Resource
    URL: http://dx.doi.org/10.1002/jlac.1995199511288
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    Paper (German National Licenses)
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