Skip to main content
Chemistry LibreTexts


  • Page ID
  • \( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \) \( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}} \)\(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\) \(\newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\) \( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\) \( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\) \( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\) \( \newcommand{\Span}{\mathrm{span}}\)

    Valence bond theory uses Lewis diagrams to depict structure and bonding of covalent entities, such as molecules and polyatomic ions, henceforth molecules. The Lewis diagram of many a molecule, however, is not consistent with the observed properties of the molecule. The Lewis diagram of some molecules suggests a ring bearing a fully conjugated \(\pi\)-electron system, or loop of \(\pi\) electrons, provided each atom in the ring is sp2- or sp-hybridized.

    • cyclobutadiene (1)


    • benzene (2)


    • cyclooctatetraene (3)


    • pyridine (4)


    • pyrrole (5)


    • cyclopentadienyl cation (6)


    • cyclopentadienyl anion (7)


    As evident from the stability of \(\pi\) electrons however, only some such rings actually have a loop of \(\pi\) electrons. Of the above examples, only the rings in 2, 4, 5, and 7 have a loop of \(\pi\) electrons. Resonance theory can predict that the rings in 2, 4, 5, and 7 have a loop of \(\pi\) electrons.



    According to resonance theory, however, the rings in 1, 3, and 6 also should have a loop of \(\pi\) electrons.


    Evidently, resonance theory is no more reliable a tool than Lewis diagrams to be used in predicting if a ring has a loop of \(\pi\) electrons. Rings whose Lewis diagram implies a loop of \(\pi\) electrons can be classified into three classes:

    1. aromatic rings
    2. antiaromatic rings
    3. nonaromatic rings

    To find whether a ring is aromatic, antiaromatic, nonaromatic, or none of the above, use the following flow chart.


    Figure 1.1.1: Flowchart for determining aromatic behavior in cyclic molecules.

    This page titled Aromatic is shared under a All Rights Reserved (used with permission) license and was authored, remixed, and/or curated by Gamini Gunawardena via source content that was edited to the style and standards of the LibreTexts platform; a detailed edit history is available upon request.

    • Was this article helpful?