Multiple-Center MO Theory Like all MOs, the following general rules apply to multiple-center MOs:

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15. Benzene and Aromaticity

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Presentation transcript:

Multiple-Center MO Theory Like all MOs, the following general rules apply to multiple-center MOs:

Multiple-Center  MOs of the Allyl Cation

Complete MO Energy Diagram of the Allyl Cation

Buta-1,3-diene MOs

Complete MO Energy Diagram of Buta-1,3-diene

Benzene Structure

Fig. 21-2, p. 855 Benzene MOs

Fig. 21-3, p. 856 Benzene MO Diagram

Heats of Hydrogenation

Hückel Rules From his observations on the structural similarities of compounds in each of these classes, Erich Hückel (1896– 1980), a German physicist and physical chemist, proposed what are now known as the Hückel rules for aromaticity: Alternatively, the Hückel numbers correspond to 4n + 2, where n is any integer >0, and the anti-Hückel numbers correspond to 4n, where n is any integer >1.

Cyclobutadiene’s π Mos The lowest-energy MO (π 1 ) has no nodal planes perpendicular to the bonding axes, and each additional nodal plane raises the energy of the other MOs.

MO Picture of Cyclobutadiene

Fig. 21-6, p. 859

 Aromatic Hydrocarbon:  Aromatic Hydrocarbon: A cyclic, planar, fully conjugated hydrocarbon with 4n+2 pi electrons (2, 6, 10, 14, 18, etc).  An aromatic hydrocarbon is especially stable relative to an open-chain fully conjugated hydrocarbon of the same number of carbon atoms.  Nonaromatic Hydrocarbon:  Nonaromatic Hydrocarbon: A cyclic, non-planar, fully conjugated hydrocarbon with 4n+2 pi electrons.  A nonaromatic hydrocarbon has similar stability to its open- chain fully conjugated hydrocarbon of the same number of carbon atoms.  Antiaromatic hydrocarbon:  Antiaromatic hydrocarbon: A monocyclic, planar, fully conjugated hydrocarbon with 4n pi electrons (4, 8, 12, 16, 20...).  An antiaromatic hydrocarbon is especially unstable relative to an open-chain fully conjugated hydrocarbon of the same number of carbon atoms.

Cycloocta-1,3,5,7-tetraene According to Hückel’s rules, [8]annulene should be antiaromatic if it is planar. Because of the instability associated with antiaromaticity, however, [8]annulene resists planarity.

Aromaticity and Multiple Rings Compounds with two or more rings can also be aromatic. These molecules are aromatic, and as a class are called polycyclic aromatic hydrocarbons (PAHs).

Other Aromatics

Heterocyclic Aromatic Compounds Heterocyclic aromatic compounds include pyridine, pyrrole, and furan.

Fig , p. 864

Fig , p. 864

p. 864 Biologically Relevant Heterocycles

Aromaticity and DNA Aromaticity affects the structure and properties DNA.