Editing Aromatic compound (section)

== Heteroarenes ==
'''Heteroarenes''' are aromatic compounds, where at least one [[Methine group|methine]] or [[Vinylene group|vinylene]] (-C= or -CH=CH-) group is replaced by a [[heteroatom]]: [[oxygen]], [[nitrogen]], or [[sulfur]].<ref>''IUPAC. Compendium of Chemical Terminology, 2nd ed. (the "Gold Book"). Compiled by A. D. McNaught and A. Wilkinson. Blackwell Scientific Publications, Oxford (1997). Online version (2019-) created by S. J. Chalk. <nowiki>ISBN 0-9678550-9-8</nowiki>. <nowiki>https://doi.org/10.1351/goldbook</nowiki>.''</ref> Examples of non-benzene compounds with aromatic properties are [[furan]], a heterocyclic compound with a five-membered ring that includes a single oxygen atom, and [[pyridine]], a heterocyclic compound with a six-membered ring containing one nitrogen atom. Hydrocarbons without an aromatic ring are called [[Aliphatic compound|aliphatic]]. Approximately half of compounds known in 2000 are described as aromatic to some extent.<ref>{{Cite journal |last1=Balaban |first1=Alexandru T. |last2=Oniciu |first2=Daniela C. |last3=Katritzky |first3=Alan R. |date=2004-05-01 |title=Aromaticity as a Cornerstone of Heterocyclic Chemistry |url=https://pubs.acs.org/doi/10.1021/cr0306790 |journal=Chemical Reviews |language=en |volume=104 |issue=5 |pages=2777–2812 |doi=10.1021/cr0306790 |pmid=15137807 |issn=0009-2665}}</ref>
[[File:Orbital_overlap_of_furan.png|class=skin-invert-image|thumb|168x168px|Electron flow through p orbitals for the heterocycle [[furan]]<ref name=":43">{{Cite book |last=Klein |first=David R. |title=Organic Chemistry |publisher=John Wiley & Sons |year=2017 |isbn=9781119444251 |edition=3rd}}</ref>]]
[[File:Pyridine_line_bond_structure.png|class=skin-invert-image|left|thumb|142x142px|Line bond structure of the heterocycle [[pyridine]]<ref name=":43" />]]
[[File:Furan_line_bond_structure.png|class=skin-invert-image|center|thumb|142x142px|Line bond structure of the heterocycle [[furan]]<ref name=":43" />]]