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Gas phase acidities of N-substituted amine-boranes

Aiko Adamson1, Jean-Claude Guillemin, Peeter Burk

  • 1Institute of Chemistry, University of Tartu, 14a Ravila St, Tartu, 50411, Estonia, adamson@ut.ee.

Journal of Molecular Modeling
|October 3, 2013
PubMed

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The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
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Basicity of Heterocyclic Aromatic Amines

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Various carboxylic acid derivatives (such as acid chlorides, esters, and anhydrides) can be used for the acylation of amines to yield amides. The reaction requires two equivalents of amines. The first amine molecule functions as a nucleophile and attacks the carbonyl carbon to produce a tetrahedral intermediate. This is followed by the loss of the leaving group and restoration of the C=O bond.
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