Adamantane: Structure & Derivatives

Instructor: Justin Wiens

Justin teaches college chemistry and has Bachelor and Doctorate degrees in chemistry.

In this lesson, we describe the organic chemical adamantane, its atomic structure, and its similarity to the covalently bonded network substance known commonly as diamond.

What is Adamantane?

If you have read the X-Men comics or have watched the movies, surely you are familiar with the character Wolverine. He has a feisty, unpredictable attitude with unstoppable, razor-sharp claws that shoot from his hands. He is a mutant who undergoes surgery to replace all the bone in his body by the nearly indestructible, but fictional, material adamantium.

Although adamantium is not a real substance, adamantane is a real, organic compound that can be synthesized in the laboratory. It has the chemical formula C10 H16 and is similar to the other real compound we know as diamond.

Physical Properties of Adamantane

Hardness

In the comics, adamantium is nearly, but not completely, indestructible, much like we consider diamond in the real world. Diamond is an extremely hard substance with strong carbon-carbon covalent bonds.

Adamantane crystals are actually much softer than diamond, though; adamantium is not a good representation of the real chemical!

Atomic Arrangement

If adamantane is so much softer than diamond, then why use it as a model for adamantium? One reason is that the arrangement of carbon atoms in diamond and in adamantane are nearly identical:


Diamond lattice, adamantane molecule
diamond lattice, adamantane molecule


In the diamond structure on the left, the ten silver carbon atoms in the center of the cube have nearly the same geometry as in the adamantane molecule shown on the right. (In the adamantane figure, the intersections of the lines represent positions of carbon atoms, which have been omitted for clarity.) The purple carbon atoms on the corners of the cube form part of an adjacent adamantane-like unit. These atoms are covalently bonded to the silver carbon atoms, forming a repeating lattice over many millions of atoms as the cubes, called unit cells, are placed next to each other.

Adamantane can form this repeating network, too. Not only is the atomic arrangement the same for diamond and adamantane, but the chemical bond lengths between the C atoms are also nearly the same! The difference is that the network of adamantane molecules is not linked by covalent bonds between the purple and silver atoms, as in diamond. Instead, the purple-silver chemical bonds could be replaced by dotted lines to indicate much weaker interactions between adamantane molecules. The weaker interactions mean that individual adamantane molecules can get ''squished'' around much easier than in diamond, making it a softer substance than diamond.

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