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Benzene, the model π system, has no permanent dipole moment, as the contributions of the weakly polar carbon–hydrogen bonds cancel due to molecular symmetry.However, the electron-rich π system above and below the benzene ring hosts a partial negative charge.
For example, the following hydrogen atom migration is of order [1,5], attained by counting counterclockwise through the π system, rather than the [1,3] order designation through the ring CH 2 group that would mistakenly result if counted clockwise. As a general approach, one can simply draw the transition state of the reaction.
In the halogenation of benzene, the sigma complex comprises the six carbon atoms of the benzene ring, each bonded to a hydrogen atom. An additional halogen atom is bonded to one of the carbon atoms, which is sp 3-hybridized, while the other carbons remain sp 2-hybridized.
In chemistry, π-effects or π-interactions are a type of non-covalent interaction that involves π systems.Just like in an electrostatic interaction where a region of negative charge interacts with a positive charge, the electron-rich π system can interact with a metal (cationic or neutral), an anion, another molecule and even another π system. [1]
The benzene dimer is the prototypical system for the study of pi stacking, and is experimentally bound by 8–12 kJ/mol (2–3 kcal/mol) in the gas phase with a separation of 4.96 Å between the centers of mass for the T-shaped dimer.
Two hydrogen atoms bonded to one carbon lie in a plane perpendicular to the benzene ring. [4] The arenium ion is no longer an aromatic species; however it is relatively stable due to delocalization: the positive charge is delocalized over 3 carbon atoms by the pi system, as depicted on the following resonance structures:
Simple aromatic rings can be heterocyclic if they contain non-carbon ring atoms, for example, oxygen, nitrogen, or sulfur. They can be monocyclic as in benzene, bicyclic as in naphthalene, or polycyclic as in anthracene. Simple monocyclic aromatic rings are usually five-membered rings like pyrrole or six-membered rings like pyridine.
It was later extended to conjugated molecules such as pyridine, pyrrole and furan that contain atoms other than carbon and hydrogen (heteroatoms). [4] A more dramatic extension of the method to include σ-electrons, known as the extended Hückel method (EHM), was developed by Roald Hoffmann .