9/19/17

Phuong Bui
CHM 223 L03
Molecular Modeling Lab Report

Exercise 1: Comparison of sp2 and sp3 Nitrogen on Imidazole

This molecular modeling lab aims to compare the basicity of two N atoms in imidazole

using resonance structures, heats of formation, and potential energy maps.

Figure 1. Reaction of imidazole with acid

The reaction scheme in figure 1 shows two conjugate acids of imidazole. The sp2 N

protonated conjugate acid is resonance stabilized, as the (+) charge moves across 2 positions of

N. The sp3 N protonated conjugate acid does not have resonance, thus is less stable. Based on

resonance stability, it is reasonable to predict that the N atom at the alkene is more basic.

Compound Heat of formation Hf

sp2 N protonated 196 kcal/mol
sp3 N protonated 234 kcal/mol

Table 1. Heat of formation of each conjugate acid

 The heat of formation for the sp2 N protonated conjugate acid is 196 kcal/mol, lower than

that of the sp3 N protonated conjugate acid which is 234 kcal/mol (Table 1). This proves the fact

that the sp2 product is more stable, as the reaction occurs more readily.

Figure 2. Potential energy maps of sp2 (left) and sp3 (right) N protonated compounds.

Furthermore, Figure 2 shows that the sp2 N protonated conjugate acid has two blue

regions which represent the (+) charge being distributed over two places, while the sp3 N

protonated compound only has one blue region. Thus, the potential energy maps prove that the

sp2 N protonated conjugate acid is resonance stabilized.

In conclusion, the sp2 N atom on imidazole is more basic because when protonated, it has

two resonance structures to distribute the (+) charge. The lower heat of formation also confirms

the stability of the conjugate acids, and the potential energy maps confirm the resonance

stability.