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Apr 26, 2013 · Resonance Structures of Aniline. 1.6K Likes. 136,920 Views. 2013 Apr 26. There are four (technically five) resonance structures for aniline. Here I show how to create them all by pushing...
Anilines are aromatic amines with the formula C6H5NH2 or C6H7N. They have various applications in industry, medicine, and agriculture, but they are also toxic and can undergo oxidation, acylation, and other reactions.
Traditionally, the weak basicity of aniline is attributed to a combination of inductive effect from the more electronegative sp 2 carbon and resonance effects, as the lone pair on the nitrogen is partially delocalized into the pi system of the benzene ring. (see the picture below):
Hint: The resonance structures of aniline are drawn by first displacing the lone pair of electrons on the nitrogen to the bond between C and N. This results in formation of a double bond between C and N with N getting a positive charge due to the donation of electrons.
Aniline derivatives also act as carbon nucleophiles due to the resonance activation of the ring. For example, arenediazonium salts, which are prepared from aniline, are great electrophiles due to the positively charged nitrogen which pulls the electron density from the ring making it susceptible to a nucleophilic attack.
Mar 13, 2024 · Resonance of Aniline. The resonance structure of aniline is shown below: The above resonance can be understood by dividing the whole resonance process in two parts: In first part, the lone pair of electrons on the nitrogen atom forms a π bond with the adjacent carbon atom, resulting in a double bond between nitrogen and carbon
Basicity of aniline. Aniline is substantially less basic than methylamine, as is evident by looking at the pK a values for their respective ammonium conjugate acids (remember that the lower the pKa of the conjugate acid, the weaker the base).
