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    Structure reactivity relationship in the accelerated formation of 2,3-diarylquinoxalines in the microdroplets of a nebuliser

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    Publication date
    2019-12-01
    Author
    Hayat, Nadia
    Fenwick, Nathan W.
    Saidykhan, Amie
    Telford, Richard
    Martin, William H.C.
    Gallagher, R.T.
    Bowen, Richard D.
    Keyword
    Diarylquinoxalines
    Hammett relationship
    Condensation
    Electrospray
    Nebuliser
    Peer-Reviewed
    Yes
    
    Metadata
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    Abstract
    Competition experiments in which 1,2-phenylenediamine, C6H4(NH2)2, condenses with equimolar quantities of benzil, (C6H5CO)2, and a 3,3'- or 4,4'-disubstituted benzil (XC6H4CO)2 (X = F, Cl, Br, CH3 or CH3O) to form a mixture of 2,3-diphenylquinoxaline and the corresponding 2,3-diarylquinoxaline (Ar = XC6H4) in the microdroplets produced in a nebuliser allow a Hammett relationship with a ρ value of 1.85 to be developed for this accelerated condensation in the nebuliser. This structure reactivity relationship reveals that an appreciable amount of negative charge builds up on the carbon of the carbonyl group of the benzil during the rate-limiting step of the reaction, thus confirming that this process involves nucleophilic addition of the 1,2-phenylenediamine to the benzil. In general, the presence of an electron donating substituent, particularly in the 4 and 4' positions, in the benzil retards the reaction, whereas an electron attracting substituent, especially in the 3 and 3' position, accelerates it.
    URI
    http://hdl.handle.net/10454/17409
    Version
    No full-text in the repository
    Citation
    Hayat N, Fenwick NW, Saidykhan A, Telford R et al (2019) Structure reactivity relationship in the accelerated formation of 2,3-diarylquinoxalines in the microdroplets of a nebuliser. European Journal of Mass Spectrometry. 25(6): 457-462.
    Link to publisher’s version
    https://doi.org/10.1177/1469066719877346
    Type
    Letter
    Collections
    Life Sciences Publications

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