Identification of cyclobutane-type dimers of substituted cinnamic acids by gas chromatography/mass spectrometry

D. Stewart, G.W. Robertson, I.M. Morrison

    Research output: Contribution to journalArticle

    Abstract

    Substituted cinnamic acids were dimerized, under fluorescent or UV light, as a glassy coating on a vial then subsequently analysed by GC/MS. Mass Spectrometric analysis of the dimers formed by each acid allowed the assignment of the dimer as a truxillic or truxinic structure since these structures had distinctive fragmentation patterns; the breakdown of the truxillic acids involves a McLafferty rearrangment before fragmentation occurs, whereas the truxinic acids, which have both carboxy groups on one side and both aromatic groups on the other, fragment asymmetrically to give characteristic stilbene and dicarboxylate fragments. It is apparent from the results of the dimerization of the lcinnamic acids that, under the conditions used here, if the monomeric acid had the capacity for hydrogen bonding using the ring substituent as well as the carboxy group, the dimerization products would be overshelmingly truxillic in structure. However, if only the carboxy group could hydrogen bond, the products would be almost exclusively traxinic in structure.
    Copyright © 1992 John Wiley & Sons, Ltd.
    Original languageEnglish
    Pages (from-to)46-53
    Number of pages8
    JournalRapid Communications in Mass Spectrometry
    Volume6
    Issue number1
    DOIs
    Publication statusPublished - Jan 1992

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    Cyclobutanes
    Gas chromatography
    Dimers
    Mass spectrometry
    Acids
    Dimerization
    Hydrogen bonds
    Stilbenes
    Ultraviolet radiation
    Coatings
    cinnamic acid

    Cite this

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    title = "Identification of cyclobutane-type dimers of substituted cinnamic acids by gas chromatography/mass spectrometry",
    abstract = "Substituted cinnamic acids were dimerized, under fluorescent or UV light, as a glassy coating on a vial then subsequently analysed by GC/MS. Mass Spectrometric analysis of the dimers formed by each acid allowed the assignment of the dimer as a truxillic or truxinic structure since these structures had distinctive fragmentation patterns; the breakdown of the truxillic acids involves a McLafferty rearrangment before fragmentation occurs, whereas the truxinic acids, which have both carboxy groups on one side and both aromatic groups on the other, fragment asymmetrically to give characteristic stilbene and dicarboxylate fragments. It is apparent from the results of the dimerization of the lcinnamic acids that, under the conditions used here, if the monomeric acid had the capacity for hydrogen bonding using the ring substituent as well as the carboxy group, the dimerization products would be overshelmingly truxillic in structure. However, if only the carboxy group could hydrogen bond, the products would be almost exclusively traxinic in structure.Copyright {\circledC} 1992 John Wiley & Sons, Ltd.",
    author = "D. Stewart and G.W. Robertson and I.M. Morrison",
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    pages = "46--53",
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    Identification of cyclobutane-type dimers of substituted cinnamic acids by gas chromatography/mass spectrometry. / Stewart, D.; Robertson, G.W.; Morrison, I.M.

    In: Rapid Communications in Mass Spectrometry, Vol. 6, No. 1, 01.1992, p. 46-53.

    Research output: Contribution to journalArticle

    TY - JOUR

    T1 - Identification of cyclobutane-type dimers of substituted cinnamic acids by gas chromatography/mass spectrometry

    AU - Stewart, D.

    AU - Robertson, G.W.

    AU - Morrison, I.M.

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    Y1 - 1992/1

    N2 - Substituted cinnamic acids were dimerized, under fluorescent or UV light, as a glassy coating on a vial then subsequently analysed by GC/MS. Mass Spectrometric analysis of the dimers formed by each acid allowed the assignment of the dimer as a truxillic or truxinic structure since these structures had distinctive fragmentation patterns; the breakdown of the truxillic acids involves a McLafferty rearrangment before fragmentation occurs, whereas the truxinic acids, which have both carboxy groups on one side and both aromatic groups on the other, fragment asymmetrically to give characteristic stilbene and dicarboxylate fragments. It is apparent from the results of the dimerization of the lcinnamic acids that, under the conditions used here, if the monomeric acid had the capacity for hydrogen bonding using the ring substituent as well as the carboxy group, the dimerization products would be overshelmingly truxillic in structure. However, if only the carboxy group could hydrogen bond, the products would be almost exclusively traxinic in structure.Copyright © 1992 John Wiley & Sons, Ltd.

    AB - Substituted cinnamic acids were dimerized, under fluorescent or UV light, as a glassy coating on a vial then subsequently analysed by GC/MS. Mass Spectrometric analysis of the dimers formed by each acid allowed the assignment of the dimer as a truxillic or truxinic structure since these structures had distinctive fragmentation patterns; the breakdown of the truxillic acids involves a McLafferty rearrangment before fragmentation occurs, whereas the truxinic acids, which have both carboxy groups on one side and both aromatic groups on the other, fragment asymmetrically to give characteristic stilbene and dicarboxylate fragments. It is apparent from the results of the dimerization of the lcinnamic acids that, under the conditions used here, if the monomeric acid had the capacity for hydrogen bonding using the ring substituent as well as the carboxy group, the dimerization products would be overshelmingly truxillic in structure. However, if only the carboxy group could hydrogen bond, the products would be almost exclusively traxinic in structure.Copyright © 1992 John Wiley & Sons, Ltd.

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