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  • Structural investigation on phenyl- and pyridin-2-ylamino(methylene)naphthalen-2(3H)-one. Substituent effects on the NMR chemical shifts

    Author(s)
    K. Venkatachalam, Taracad
    K. Pierens, Gregory
    Campitelli, Marc
    C. Reutens, David
    Griffith University Author(s)
    Campitelli, Marc R.
    Year published
    2010
    Metadata
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    Abstract
    Schiff bases bearing phenyl and pyridyl groups were synthesized by condensation of appropriate amines with 2-hydroxynaphthaldehyde. These Schiff bases were obtained as colored crystalline solids. The proton NMR spectra of these compounds showed a doublet for the NH protons indicating a keto tautomer for these Schiff bases. The pyridyl-substituted Schiff bases containing hydroxyl moiety were found to show the most downfield shift for the NH protons in DMSO solvent, and this was rationalized due to the formation of a six- and five-membered ring using hydrogen bonds for these two compounds. Correspondingly, the olefinic proton ...
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    Schiff bases bearing phenyl and pyridyl groups were synthesized by condensation of appropriate amines with 2-hydroxynaphthaldehyde. These Schiff bases were obtained as colored crystalline solids. The proton NMR spectra of these compounds showed a doublet for the NH protons indicating a keto tautomer for these Schiff bases. The pyridyl-substituted Schiff bases containing hydroxyl moiety were found to show the most downfield shift for the NH protons in DMSO solvent, and this was rationalized due to the formation of a six- and five-membered ring using hydrogen bonds for these two compounds. Correspondingly, the olefinic proton of the Schiff bases is also found to be a doublet due to coupling to the amine proton. These Schiff bases exhibited thermochromic properties. Detailed NMR spectral analysis for both the phenyl- and pyridyl-substituted Schiff bases is presented.
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    Journal Title
    Magnetic Resonance in Chemistry
    Volume
    48
    Issue
    8
    DOI
    https://doi.org/10.1002/mrc.2626
    Subject
    Physical Chemistry not elsewhere classified
    Medicinal and Biomolecular Chemistry
    Physical Chemistry (incl. Structural)
    Publication URI
    http://hdl.handle.net/10072/36955
    Collection
    • Journal articles

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