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- Aromaticity abstract "In organic chemistry, the term aromaticity is used to describe a cyclic (ring-shaped), planar (flat) molecule that exhibits unusual stability as compared to other geometric or connective arrangements of the same set of atoms. As a result of their stability, it is very difficult to cause aromatic molecules to break apart and to react with other substances. Organic compounds that are not aromatic are classified as aliphatic compounds—they might be cyclic, but only aromatic rings have especial stability (low reactivity).Since one of the most commonly encountered aromatic systems of compounds in organic chemistry is based on derivatives of the prototypical aromatic compound benzene (an aromatic hydrocarbon common in petroleum and its distillates), the word “aromatic” is occasionally used to refer informally to benzene derivatives, and this is how it was first defined. Nevertheless, many non-benzene aromatic compounds exist. In living organisms, for example, the most common aromatic rings are the double-ringed bases in RNA and DNA. A functional group or other substituent that is aromatic is called an aryl group.The earliest use of the term “aromatic” was in an article by August Wilhelm Hofmann in 1855. Hofmann used the term for a class of benzene compounds, many of which do have odors (aromas), unlike pure saturated hydrocarbons. Today, there is no general relationship between aromaticity as a chemical property and the olfactory properties of such compounds (how they smell), although in 1855, before the structure of benzene or organic compounds was understood, chemists like Hofmann were beginning to understand that odiferous molecules from plants, such as terpenes, had chemical properties we recognize today are similar to unsaturated petroleum hydrocarbons like benzene.In terms of the electronic nature of the molecule, aromaticity describes a conjugated system often made of alternating single and double bonds in a ring. This configuration allows for the electrons in the molecule’s pi system to be delocalized around the ring, increasing the molecule's stability. The molecule cannot be represented by one structure, but rather a resonance hybrid of different structures, such as with the two resonance structures of benzene. These molecules cannot be found in either one of these representations, with the longer single bonds in one location and the shorter double bond in another (See Theory below). Rather, the molecule exhibits bond lengths in between those of single and double bonds. This commonly seen model of aromatic rings, namely the idea that benzene was formed from a six-membered carbon ring with alternating single and double bonds (cyclohexatriene), was developed by August Kekulé (see History section below). The model for benzene consists of two resonance forms, which corresponds to the double and single bonds superimposing to produce six one-and-a-half bonds. Benzene is a more stable molecule than would be expected without accounting for charge delocalization.".
- Aromaticity thumbnail Benzene_resonance_structures.png?width=300.
- Aromaticity wikiPageID "239836".
- Aromaticity wikiPageLength "27907".
- Aromaticity wikiPageOutDegree "155".
- Aromaticity wikiPageRevisionID "704650266".
- Aromaticity wikiPageWikiLink Adenine.
- Aromaticity wikiPageWikiLink Alicyclic_compound.
- Aromaticity wikiPageWikiLink Aliphatic_compound.
- Aromaticity wikiPageWikiLink Aniline.
- Aromaticity wikiPageWikiLink Annulation.
- Aromaticity wikiPageWikiLink Annulene.
- Aromaticity wikiPageWikiLink Anthracene.
- Aromaticity wikiPageWikiLink Antiaromaticity.
- Aromaticity wikiPageWikiLink Arenium_ion.
- Aromaticity wikiPageWikiLink Aromatic_amine.
- Aromaticity wikiPageWikiLink Aromatic_hydrocarbon.
- Aromaticity wikiPageWikiLink Aromatic_ring_current.
- Aromaticity wikiPageWikiLink Aryl.
- Aromaticity wikiPageWikiLink Aspirin.
- Aromaticity wikiPageWikiLink Atomic_orbital.
- Aromaticity wikiPageWikiLink August_Kekulé.
- Aromaticity wikiPageWikiLink August_Wilhelm_von_Hofmann.
- Aromaticity wikiPageWikiLink Avoided_crossing.
- Aromaticity wikiPageWikiLink Benzene.
- Aromaticity wikiPageWikiLink Benzimidazole.
- Aromaticity wikiPageWikiLink Bond_length.
- Aromaticity wikiPageWikiLink Borazine.
- Aromaticity wikiPageWikiLink Carbo-mer.
- Aromaticity wikiPageWikiLink Category:Aromatic_compounds.
- Aromaticity wikiPageWikiLink Category:Physical_organic_chemistry.
- Aromaticity wikiPageWikiLink Chemical_compound.
- Aromaticity wikiPageWikiLink Chemical_reaction.
- Aromaticity wikiPageWikiLink Chirality_(chemistry).
- Aromaticity wikiPageWikiLink Chlorophyll.
- Aromaticity wikiPageWikiLink Computational_chemistry.
- Aromaticity wikiPageWikiLink Conjugated_system.
- Aromaticity wikiPageWikiLink Coplanarity.
- Aromaticity wikiPageWikiLink Covalent_bond.
- Aromaticity wikiPageWikiLink Cyclic_compound.
- Aromaticity wikiPageWikiLink Cyclobutadiene.
- Aromaticity wikiPageWikiLink Cyclodecapentaene.
- Aromaticity wikiPageWikiLink Cyclooctatetraene.
- Aromaticity wikiPageWikiLink Cyclotetradecaheptaene.
- Aromaticity wikiPageWikiLink Cytosine.
- Aromaticity wikiPageWikiLink DNA.
- Aromaticity wikiPageWikiLink Delocalized_electron.
- Aromaticity wikiPageWikiLink Double_bond.
- Aromaticity wikiPageWikiLink Electron.
- Aromaticity wikiPageWikiLink Electrophilic_addition.
- Aromaticity wikiPageWikiLink Electrophilic_aromatic_substitution.
- Aromaticity wikiPageWikiLink Erich_Clar.
- Aromaticity wikiPageWikiLink Erich_Hückel.
- Aromaticity wikiPageWikiLink Functional_group.
- Aromaticity wikiPageWikiLink Furan.
- Aromaticity wikiPageWikiLink Guanidine.
- Aromaticity wikiPageWikiLink Guanine.
- Aromaticity wikiPageWikiLink Handedness.
- Aromaticity wikiPageWikiLink Heme.
- Aromaticity wikiPageWikiLink Henry_Edward_Armstrong.
- Aromaticity wikiPageWikiLink Heterocyclic_compound.
- Aromaticity wikiPageWikiLink Histidine.
- Aromaticity wikiPageWikiLink Homoaromaticity.
- Aromaticity wikiPageWikiLink Hunds_rule_of_maximum_multiplicity.
- Aromaticity wikiPageWikiLink Hxc3xbcckels_rule.
- Aromaticity wikiPageWikiLink Imidazole.
- Aromaticity wikiPageWikiLink J._J._Thomson.
- Aromaticity wikiPageWikiLink Johann_Benedict_Listing.
- Aromaticity wikiPageWikiLink Metal_aromaticity.
- Aromaticity wikiPageWikiLink Molecular_orbital.
- Aromaticity wikiPageWikiLink Molecule.
- Aromaticity wikiPageWikiLink Möbius_aromaticity.
- Aromaticity wikiPageWikiLink Möbius_strip.
- Aromaticity wikiPageWikiLink Möbius–Hückel_concept.
- Aromaticity wikiPageWikiLink Naphthalene.
- Aromaticity wikiPageWikiLink Nuclear_magnetic_resonance.
- Aromaticity wikiPageWikiLink Nucleophilic_aromatic_substitution.
- Aromaticity wikiPageWikiLink Nucleotide.
- Aromaticity wikiPageWikiLink Nylon.
- Aromaticity wikiPageWikiLink Odor.
- Aromaticity wikiPageWikiLink Olfaction.
- Aromaticity wikiPageWikiLink Open_shell.
- Aromaticity wikiPageWikiLink Orbital_hybridisation.
- Aromaticity wikiPageWikiLink Organic_chemistry.
- Aromaticity wikiPageWikiLink Organic_compound.
- Aromaticity wikiPageWikiLink Oxazole.
- Aromaticity wikiPageWikiLink Paracetamol.
- Aromaticity wikiPageWikiLink Paradromic.
- Aromaticity wikiPageWikiLink Petrochemical.
- Aromaticity wikiPageWikiLink Petroleum.
- Aromaticity wikiPageWikiLink Phenanthrene.
- Aromaticity wikiPageWikiLink Phenol.
- Aromaticity wikiPageWikiLink Phenyl_group.
- Aromaticity wikiPageWikiLink Phenylalanine.
- Aromaticity wikiPageWikiLink Pi_bond.
- Aromaticity wikiPageWikiLink Pi_interaction.
- Aromaticity wikiPageWikiLink Plane_(geometry).
- Aromaticity wikiPageWikiLink Plant.
- Aromaticity wikiPageWikiLink Polycyclic_aromatic_hydrocarbon.
- Aromaticity wikiPageWikiLink Polyester.