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In chemistry, the double bond rule states that elements with a principal quantum number (n) greater than 2 for their valence electrons (period 3 elements and higher) tend not to form multiple bonds (e.g. double bonds and triple bonds). The double bonds, when they exist, are often weak due to poor orbital overlap between the n>2 orbitals of the two atoms. Although such compounds are not intrinsically unstable, they instead tend to polymerize. An example is the rapid polymerization that occurs upon condensation of disulfur, the heavy analogue of O2. Numerous exceptions to the rule exist. Triple bonds Other meanings Another unrelated double bond rule exists that relates to the enhanced reactivity of sigma bonds attached to an atom adjacent to a double bond. In bromoalkenes, the C–Br bond is very stable, but in an allyl bromide, this bond is very reactive. Likewise, bromobenzenes are generally inert, whereas benzylic bromides are reactive. The first to observe the phenomenon was Conrad Laar in 1885. The name for the rule was coined by Otto Schmidt in 1932. References. Discover the Daniel Fettinger popular books. Find the top 100 most popular Daniel Fettinger books.