If you like us, please share us on social media, tell your friends, tell your professor or consider building or adopting a Wikitext for your course.
Amides are neutral compounds -- in contrast to their seemingly close relatives, the amines, which are basic. The amide linkage is planar -- even though we normally show the C-N connected by a single bond, which should provide free rotation. Fig 1 below shows this common drawing of an amide.
Fig 1. An amide; usual representation. The amide shown here, and in Fig 2, is the primary amide from ethanoic acid (acetic acid); the amide is called ethanamide (acetamide).
To help understand these properties, we need to look at a more complex -- but better -- representation of the amide structure. This is shown in Fig 2:
Fig 2. Resonance structures for an amide. Remember that the molecule does not actually switch between these structures. Instead, the actual structure is somewhere in between the structures shown. It can be thought of as some average of these structures.
Why is this resonance system better? A qualitative argument is that the O, which is very electronegative, draws electrons toward it. In this case, it draws electrons from the lone pair of the N. Note that in the right hand form, the electrons of the N lone pair have moved in to the double bond (giving the N a + charge), and electrons of the C=O double bond have moved out to the O (giving it a - charge).
The resonance system shown in Fig 2 is based on measurements of the properties of amides. That is, detailed study of amides shows that the properties are better explained by Fig 2 than by Fig 1. As examples:
This material is based upon work supported by the National Science Foundation under Grant Number 1246120