imported>Hydrogen Sulfide |
imported>Hydrogen Sulfide |
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| == 3-membered rings ==
| |
| Although subject to ring strain, 3-membered heterocyclic rings are well characterized.<ref>{{March6th}}</ref>
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|
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| ===Three-membered rings with one heteroatom===
| |
| {| class="wikitable" | | {| class="wikitable" |
| !Heteroatom
| | | || || || || || || || || || |
| !Saturated
| |
| !Unsaturated
| |
| |- | | |- |
| | Boron | | | || || || || || || || || || |
| | Borirane | |
| | Borirene | |
| |- | | |- |
| | Nitrogen | | | || || || || || || || || || |
| | Aziridine | |
| | Azirine | |
| |- | | |- |
| | Oxygen | | | || || || || || || || || || |
| | Oxirane (ethylene oxide, epoxides) | |
| | Oxirene | |
| |- | | |- |
| | Phosphorus | | | || || || || || || || || || |
| | Phosphirane | |
| | Phosphirene | |
| |- | | |- |
| | Sulfur | | | || || || || || || || || || |
| | Thiirane (episulfides) | |
| | Thiirene | |
| |} | |
| | |
| ===Three-membered rings with two heteroatoms===
| |
| | |
| {| class="wikitable"
| |
| !Heteroatoms
| |
| !Saturated
| |
| !Unsaturated
| |
| |- | |
| | 2× Nitrogen | |
| | Diaziridine | |
| | Diazirine | |
| |- | |
| | Nitrogen + oxygen | |
| | Oxaziridine
| |
| | Oxazirine
| |
| |-
| |
| | 2× Oxygen
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| | Dioxirane<br>(highly unstable)
| |
| |
| |
| |}
| |
| | |
| == 4-membered rings ==
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| ===Four-membered rings with ''one'' heteroatom===
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| | |
| {| class="wikitable"
| |
| |-
| |
| ! Heteroatom
| |
| ! Saturated
| |
| ! Unsaturated
| |
| |-
| |
| | Nitrogen
| |
| | Azetidine
| |
| | Azete
| |
| |-
| |
| | Oxygen
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| | Oxetane
| |
| | Oxete
| |
| |-
| |
| |Phosphorus
| |
| |Phosphetane
| |
| |Phosphete
| |
| |-
| |
| | Sulfur
| |
| | Thietane
| |
| | Thiete
| |
| |}
| |
| | |
| ===Four-membered rings with ''two'' heteroatoms===
| |
| | |
| {| class="wikitable"
| |
| ! Heteroatoms
| |
| ! Saturated
| |
| ! Unsaturated
| |
| |-
| |
| | 2× Nitrogen
| |
| | Diazetidine
| |
| | Diazete
| |
| |-
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| | 2× Oxygen
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| | Dioxetane
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| | Dioxete
| |
| |-
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| | 2× Sulfur
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| | Dithietane
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| | Dithiete
| |
| |}
| |
| | |
| == 5-membered rings ==
| |
| ===Five-membered rings with ''one'' heteroatom===
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| | |
| {| class="wikitable"
| |
| |-
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| ! Heteroatom
| |
| ! Saturated
| |
| ! Unsaturated
| |
| |-
| |
| | Antimony
| |
| | Stibolane
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| | Stibole
| |
| |-
| |
| | Arsenic
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| | Arsolane
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| | Arsole
| |
| |-
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| | Bismuth
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| | Bismolane
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| | Bismole
| |
| |-
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| | Boron
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| | Borolane
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| | Borole
| |
| |-
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| | Nitrogen
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| | ''Pyrrolidine'' ("Azolidine" is not used)
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| | ''Pyrrole'' ("Azole" is not used)
| |
| |-
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| | Oxygen
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| | Oxolane
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| | Furan
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| |-
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| | Phosphorus
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| | Phospholane
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| | Phosphole
| |
| |-
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| | Selenium
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| | Selenolane
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| | Selenophene
| |
| |-
| |
| | Silicon
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| | Silacyclopentane
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| | Silole
| |
| |-
| |
| | Sulfur
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| | Thiolane
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| | ''Thiophene''
| |
| |-
| |
| | Tellurium
| |
| |
| |
| | Tellurophene
| |
| |-
| |
| | Tin
| |
| | Stannolane
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| | Stannole | |
| |} | |
| | |
| ===Five-membered rings with ''two'' heteroatoms===
| |
| The 5-membered ring compounds containing ''two'' heteroatoms, at least one of which is nitrogen, are collectively called the azoles. Thiazoles and isothiazoles contain a sulfur and a nitrogen atom in the ring. Dithiolanes have two sulfur atoms.
| |
| | |
| {| class="wikitable"
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| ! Heteroatoms
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| ! Saturated
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| ! Unsaturated (and partially unsaturated)
| |
| |- valign=top | |
| ! 2× nitrogen
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| | ''Imidazolidine'' <br>''Pyrazolidine'' | |
| | ''Imidazole'' (Imidazoline)<br>''Pyrazole'' (Pyrazoline) | |
| |- valign=top
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| ! Oxygen + sulfur
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| | 1,3-Oxathiolane<br>1,2-Oxathiolane
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| | Oxathiole (Oxathioline)<br>Isoxathiole
| |
| |- valign=top
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| ! Nitrogen + Oxygen
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| | Oxazolidine<br>Isoxazolidine
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| | Oxazole (Oxazoline)<br>Isoxazole
| |
| |- valign=top
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| ! Nitrogen + sulfur
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| | Thiazolidine<br>Isothiazolidine
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| | Thiazole (Thiazoline)<br>Isothiazole
| |
| |- valign=top
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| ! 2× oxygen
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| | Dioxolane
| |
| |
| |
| |- valign=top
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| ! 2× sulfur
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| | Dithiolane
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| | Dithiole
| |
| |}
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| | |
| ===Five-membered rings with at least ''three'' heteroatoms===
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| A large group of 5-membered ring compounds with ''three'' or more heteroatoms also exists. One example is the class of dithiazoles, which contain two sulfur atoms and one nitrogen atom.
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| | |
| {| class="wikitable"
| |
| |-
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| ! Heteroatoms
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| ! Saturated
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| ! Unsaturated
| |
| |-
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| ! N N N
| |
| |
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| | Triazoles
| |
| |-
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| ! N N O
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| |
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| | Furazan<br>Oxadiazole
| |
| |-
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| ! N N S
| |
| |
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| | Thiadiazole
| |
| |-
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| ! N O O
| |
| |
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| | Dioxazole
| |
| |-
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| ! N S S
| |
| |
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| | Dithiazole
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| |-
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| ! N N N N
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| |
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| |Tetrazole
| |
| |-
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| ! N N N N O
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| |
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| | Oxatetrazole
| |
| |-
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| ! N N N N S
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| |
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| | Thiatetrazole
| |
| |-
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| ! N N N N N
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| |
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| | Pentazole
| |
| |}
| |
| | |
| == 6-membered rings ==
| |
| ===Six-membered rings with ''one'' heteroatom===
| |
| | |
| {| class="wikitable"
| |
| ! Heteroatom
| |
| ! Saturated
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| ! Unsaturated
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| ! Ions
| |
| |-
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| | Antimony
| |
| |
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| | Stibinin
| |
| |-
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| | Arsenic
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| | Arsinane
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| | Arsinine
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| |-
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| | Bismuth
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| |
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| | Bismin
| |
| |-
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| | Boron
| |
| | Borinane
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| | Borinine
| |
| | Boratabenzene anion
| |
| |-
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| | Germanium
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| | Germinane
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| | Germine
| |
| |-
| |
| | Nitrogen
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| | ''Piperidine''<br>(Azinane is not used)
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| | ''Pyridine''<br>(Azine (heterocycle)|Azine is not used)
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| | Pyridinium cation
| |
| |-
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| | Oxygen
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| | Oxane
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| | ''Pyran''<br>(2''H''-Oxine is not used)
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| | Pyrylium cation
| |
| |-
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| | Phosphorus
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| | Phosphinane
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| | Phosphinine
| |
| |-
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| | Selenium
| |
| | Selenane
| |
| | Selenopyran
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| | Selenopyrylium cation
| |
| |-
| |
| | Silicon
| |
| | Silinane
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| | Siline
| |
| |-
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| | Sulfur
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| | Thiane
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| | ''Thiopyran''<br>(2''H''-Thiine is not used)
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| | Thiopyrylium cation
| |
| |-
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| | Tellurium
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| | Tellurane
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| | Telluropyran
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| | Telluropyrylium cation
| |
| |-
| |
| | Tin
| |
| | Stanninane
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| | Stannine
| |
| |}
| |
| | |
| ===Six-membered rings with ''two'' heteroatoms===
| |
| | |
| {| class="wikitable" width=400px
| |
| |-
| |
| ! Heteroatom
| |
| ! Saturated
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| ! Unsaturated
| |
| |-
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| | Nitrogen / nitrogen
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| | Diazinane
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| | Diazine
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| |-
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| | Oxygen / nitrogen
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| | ''Morpholine''
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| | Oxazine
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| |-
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| | Sulfur / nitrogen
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| | ''Thiomorpholine''
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| | Thiazine
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| |-
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| | Oxygen / Sulfur
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| | ''Oxathiane''
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| | Oxathiin
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| |-
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| | Oxygen / oxygen
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| | Dioxane
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| | 1,4-Dioxin|Dioxine
| |
| |-
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| | Sulfur / sulfur
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| | Dithiane
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| | Dithiin
| |
| |-
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| | Boron / nitrogen
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| |
| |
| | 1,2-Dihydro-1,2-azaborine
| |
| |}
| |
| | |
| ===Six-membered rings with ''three'' heteroatoms===
| |
| | |
| {| class="wikitable" width=400px
| |
| |-
| |
| ! Heteroatom
| |
| ! Saturated
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| ! Unsaturated
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| |-
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| | Nitrogen
| |
| | Triazinane
| |
| | Triazine
| |
| |-
| |
| | Oxygen
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| | Trioxane
| |
| |
| |
| |-
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| | Sulfur
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| | Trithiane
| |
| |
| |
| |}
| |
| | |
| ===Six-membered rings with ''four'' heteroatoms===
| |
| | |
| {| class="wikitable" width=400px
| |
| |-
| |
| ! Heteroatom
| |
| ! Saturated
| |
| ! Unsaturated
| |
| |-
| |
| | Nitrogen
| |
| |
| |
| | Tetrazine
| |
| |}
| |
| | |
| Carborazine is a six-membered ring with two nitrogen heteroatoms and two boron heteroatom.
| |
| | |
| ===Six-membered rings with five heteroatoms===
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| | |
| {| class="wikitable" width=400px
| |
| |-
| |
| ! Heteroatom
| |
| ! Saturated
| |
| ! Unsaturated
| |
| |-
| |
| | Nitrogen
| |
| |
| |
| | Pentazine
| |
| |}
| |
| | |
| ===Six-membered rings with six heteroatoms===
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| The hypothetical chemical compound with six nitrogen heteroatoms would be hexazine.
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| | |
| Borazine is a six-membered ring with three nitrogen heteroatoms and three boron heteroatoms.
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| | |
| == 7-membered rings ==
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| In a 7-membered ring, the heteroatom must be able to provide an empty π-orbital (e.g. boron) for "normal" aromatic stabilization to be available; otherwise, homoaromaticity may be possible. Compounds with one heteroatom include:
| |
| | |
| {| class="wikitable"
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| ! Heteroatom
| |
| ! Saturated
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| ! Unsaturated
| |
| |-
| |
| |Boron
| |
| |
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| |Borepin
| |
| |-
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| |Nitrogen
| |
| | Azepane
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| | Azepine
| |
| |-
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| |Oxygen
| |
| | Oxepane
| |
| | Oxepine
| |
| |-
| |
| |Sulfur
| |
| | Thiepane
| |
| | Thiepine
| |
| |}
| |
| | |
| Those with two heteroatoms include:
| |
| | |
| {| class="wikitable"
| |
| |-
| |
| ! Heteroatom
| |
| ! Saturated
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| ! Unsaturated
| |
| |-
| |
| | Nitrogen
| |
| | Diazepane
| |
| | Diazepine
| |
| |-
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| | Nitrogen/sulfur
| |
| |
| |
| | Thiazepine
| |
| |}
| |
| | |
| == 8-membered rings ==
| |
| {| class="wikitable"
| |
| |-
| |
| ! Heteroatom
| |
| ! Saturated
| |
| ! Unsaturated
| |
| |-
| |
| | Nitrogen
| |
| | Azocane
| |
| | Azocine
| |
| |-
| |
| | Oxygen
| |
| | Oxocane
| |
| | Oxocine
| |
| |-
| |
| | Sulfur
| |
| | Thiocane
| |
| | Thiocine
| |
| |}
| |
| | |
| Borazocine is an eight-membered ring with four nitrogen heteroatoms and four boron heteroatoms.
| |
| | |
| == 9-membered rings ==
| |
| {| class="wikitable"
| |
| |-
| |
| ! Heteroatom
| |
| ! Saturated
| |
| ! Unsaturated
| |
| |-
| |
| | Nitrogen
| |
| | Azonane
| |
| | Azonine
| |
| |-
| |
| |Oxygen
| |
| | Oxonane | |
| | Oxonine | |
| |- | | |- |
| |Sulfur | | | || || || || || || || || || |
| | Thionane | |
| | (2Z,4Z,6Z,8Z)-Thionine|Thionine | |
| |- | | |- |
| | | || || || || || || || || || |
| |} | | |} |