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Simple aromatic ring
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==Heterocyclic aromatic rings== {| border="1" cellpadding="0" cellspacing="0" align="right" style="margin-left: 1em" | {| border="0" cellpadding="5" cellspacing="0" style="margin: 1em" ! colspan="3" align="center" | Table of simple aromatic rings |- ! Five-membered rings ! colspan="2" | Fused five-membered rings with six-membered rings | |- align="center" valign="bottom" | [[File:Pyrrole structure.png|70px]]<br>[[Pyrrole]] | [[File:Indole structure.png|120px]]<br>[[Indole]] | [[File:Carbazol - Carbazole.svg|170px]]<br>[[Carbazole]] |- align="center" valign="bottom" | [[File:Furan structure.png|70px]]<br>[[Furan]] | [[File:Benzofuran structure.png|120px]]<br>[[Benzofuran]] | [[File:Dibenzofuran - Dibenzofuran.svg|170px]]<br>[[Dibenzofuran]] |- align="center" valign="bottom" | [[File:Thiophene structure.png|70px]]<br>[[Thiophene]] | [[File:Benzothiophene structure.png|120px]]<br>[[Benzothiophene]] |[[File:Dibenzothiophen - Dibenzothiophene.svg|170px]]<br>[[Dibenzothiophene]] |- align="center" valign="bottom" | [[File:Imidazole structure.png|70px]]<br>[[Imidazole]] | [[File:Benzimidazole structure.png|120px]]<br>[[Benzimidazole]] | [[File:Purine structure.png|120px]]<br>[[Purine]] |- align="center" valign="bottom" | [[File:Pyrazole structure.png|70px]]<br>[[Pyrazole]] | [[File:Indazol.svg|120px]]<br>[[Indazole]] | |- align="center" valign="bottom" | [[File:Oxazole structure.png|70px]]<br>[[Oxazole]] | [[File:Benzoxazole structure.png|120px]]<br>[[Benzoxazole]] | |- align="center" valign="bottom" | [[File:Thiazole structure.png|70px]]<br>[[Thiazole]] | [[File:Benzothiazole structure.png|120px]]<br>[[Benzothiazole]] | |- align="center" valign="bottom" | [[File:1,2,3-Triazole structure.svg|90px]]<br>[[1,2,3-Triazole]] | [[File:1,2,4-Triazole structure.svg|90px]]<br>[[1,2,4-Triazole]] | |- ! Six-membered rings ! colspan="2" | Fused six-membered rings with six-membered rings | |- align="center" valign="bottom" | [[File:Benzene-Kekule-2D-skeletal.png|70px]]<br>[[Benzene]] | [[File:Naphthalene-2D-Skeletal.svg|120px]]<br>[[Naphthalene]] | [[File:Anthracene structure.png|170px]]<br>[[Anthracene]] |- align="center" valign="bottom" | [[File:Pyridine structure.png|70px]]<br>[[Pyridine]] | [[File:Quinoline structure.png|120px]]<br>[[Quinoline]] | [[File:Acridin.svg|170px]]<br>[[Acridine]] |- align="center" valign="bottom" | [[File:Pyrazine structure.png|70px]]<br>[[Pyrazine]] | [[File:Quinoxaline structure.png|120px]]<br>[[Quinoxaline]] | [[File:Phenazine.png|170px]]<br>[[Phenazine]] |- align="center" valign="bottom" | [[File:Pyrimidine structure.png|70px]]<br>[[Pyrimidine]] | [[File:Quinazoline structure.png|120px]]<br>[[Quinazoline]] | [[File:Pteridin - Pteridine.svg|120px]]<br>[[Pteridine]] |- align="center" valign="bottom" | [[File:Pyridazine structure.png|70px]]<br>[[Pyridazine]] | [[File:Cinnoline structure.png|120px]]<br>[[Cinnoline]] | [[File:Phthalazin - Phthalazine.svg|120px]]<br>[[Phthalazine]] |- align="center" valign="bottom" | [[File:1,2,3-Triazin - 1,2,3-triazine.svg|70px]]<br>[[1,2,3-Triazine]] | [[File:1,2,4-Triazin - 1,2,4-triazine.svg|70px]]<br>[[1,2,4-Triazine]] | [[File:1,3,5-Triazin - 1,3,5-triazine.svg|70px]]<br>[[1,3,5-Triazine]] |} |} The nitrogen (N)-containing aromatic rings can be separated into [[basic aromatic ring]]s that are easily [[protonation|protonated]], and form aromatic [[cation]]s and [[salts]] (e.g., [[pyridinium]]), and non-basic aromatic rings. *In the '''basic aromatic rings''', the [[lone pair]] of [[electron]]s is not part of the aromatic system and extends in the plane of the ring. This lone pair is responsible for the basicity of these [[nitrogenous base]]s, similar to the nitrogen atom in [[amine]]s. In these compounds, the nitrogen atom is ''not'' connected to a hydrogen atom. Examples of basic aromatic rings are [[pyridine]] or [[quinoline]]. Several rings contain basic as well as non-basic nitrogen atoms, e.g., [[imidazole]] and [[purine]]. *In the '''non-basic rings''', the lone pair of electrons of the nitrogen atom is delocalized and contributes to the aromatic pi-electron system. In these compounds, the nitrogen atom ''is'' connected to a hydrogen atom. Examples of non-basic nitrogen-containing aromatic rings are [[pyrrole]] and [[indole]]. In the oxygen- and sulfur-containing aromatic rings, one of the electron pairs of the heteroatoms contributes to the aromatic system (similar to the non-basic nitrogen-containing rings), whereas the second lone pair extends in the plane of the ring (similar to the primary nitrogen-containing rings).
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