atoms will be chiral because there will no longer be any mirror planes. The chirality of these types of allenes was first predicted in 1875 by Jacobus Henricus van 't Hoff, but not proven experimentally until 1935. Where A has a greater priority than B according to the Cahn–Ingold–Prelog priority rules, the configuration of the axial chirality can be determined by considering the substituents on the front atom followed by the back atom when viewed along the allene axis. For the back atom, only the group of higher priority need be considered. Chiral allenes have been recently used as building blocks in the construction of organic materials with exceptional chiroptical properties. There are a few examples of drug molecule having an allene system in their structure. Mycomycin, an antibiotic with tuberculostatic properties, is a typical example. This drug exhibits enantiomerism due to the presence of a suitably substituted allene system. Although the semi-localized textbook σ-π separation model describes the bonding of allene using a pair of localized orthogonal π orbitals, the full molecular orbital description of the bonding is more subtle. The symmetry-correct doubly-degenerate HOMOs of allene (adapted to the D2d point group) can either be represented by a pair of orthogonal MOs or as twisted helical linear combinations of these orthogonal MOs. The symmetry of the system and the degeneracy of these orbitals imply that both descriptions are correct (in the same way that there are infinitely many ways to depict the doubly-degenerate HOMOs and LUMOs of benzene that correspond to different choices of eigenfunctions in a two-dimensional eigenspace). However, this degeneracy is lifted in substituted allenes, and the helical picture becomes the only symmetry-correct description for the HOMO and HOMO–1 of the C2-symmetric 1,3-dimethylallene. This qualitative MO description extends to higher odd-carbon cumulenes (e.g., 1,2,3,4-pentatetraene). Chemical and spectral properties Allenes differ considerably from other alkenes in terms of their chemical properties. Compared to isolated and conjugated dienes, they are considerably less stable: comparing the isomeric pentadienes, the allenic 1,2-pentadiene has a heat of formation of 33.6 kcal/mol, compared to 18.1 kcal/mol for (E)-1,3-pentadiene and 25.4 kcal/mol for the isolated 1,4-pentadiene. The C–H bonds of allenes are considerably weaker and more acidic compared to typical vinylic C–H bonds: the bond dissociation energy is 87.7 kcal/mol (compared to 111 kcal/mol in ethylene), while the gas-phase acidity is 381 kcal/mol (compared to 409 kcal/mol for ethylene), making it slightly more acidic