In this paper we address the long standing problem regarding the site for gas-phase protonation in aniline and substituted anilines. Our study reveals that DFT-based reactivity descriptors can reproduce the experimentally observed preferable protonation sites. However, it is found that the quantity /, termed “relative nucleophilicity” and a measure of “local polarizability”, produces more reliable results than the local softness, . The problem which sometimes arises in taking / as the reactivity descriptor is also discussed.
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Roy et al. (1998) studied this question.
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