Electronegativity
Consider the basicity or nucleophilicity of various anions. Such determination is important in determining the direction and extent of acid–base reactions and to some extent the reactivity of anionic species as nucleophiles in reactions of organic chemistry. Consider the basicity of four anions: methide, amide, hydroxide, and fluoride. The electronegativity of the charged atoms in this series increases in the order given, as can be predicted by the periodic trends for elements in the same period. Figure 1 shows that the more electronegative the element in the period, the more stable the negative charge on that atom. Therefore, the basicity or nucleophilicity of these anions decrease in the order given. This approach works well when considering anions within the same period. An example of the use of hydroxide as a nucleophile in an organic chemical reaction is shown in Figure 2. The treatment of concepts within the six pillars is necessarily (and intentionally) limited: they provide a framework, but must be supplemented by many other important factors during the typical organic chemistry course. Students at all levels of chemistry should be encouraged to develop an increasing subtlety and judgment in concept application. There are many cases where valid concepts disagree and must be weighed, such as the resonance effect and the inductive effect on aromatic reactivity towards electrophiles. Biochemical example: the basicity of biochemically important amines, compared to neutral alcohols (Figure 3). Nitrogen, being less electronegative than oxygen, less effectively stabilizes the lone pair of electrons, resulting in greater electron-pair reactivity (basicity). Instructors may use this opportunity to impress on students that it is the stability of the lone pair(s) (and not the number of lone pairs) that is important.