User:Hydrogen Sulfide/沙盒
3-membered rings
Although subject to ring strain, 3-membered heterocyclic rings are well characterized.[1]
Three-membered rings with one heteroatom
| 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
| Heteroatoms | Saturated | Unsaturated |
|---|---|---|
| 2× Nitrogen | Diaziridine | Diazirine |
| Nitrogen + oxygen | Oxaziridine | Oxazirine |
| 2× Oxygen | Dioxirane (highly unstable) |
4-membered rings
Four-membered rings with one heteroatom
| Heteroatom | Saturated | Unsaturated |
|---|---|---|
| Nitrogen | Azetidine | Azete |
| Oxygen | Oxetane | Oxete |
| Phosphorus | Phosphetane | Phosphete |
| Sulfur | Thietane | Thiete |
Four-membered rings with two heteroatoms
| Heteroatoms | Saturated | Unsaturated |
|---|---|---|
| 2× Nitrogen | Diazetidine | Diazete |
| 2× Oxygen | Dioxetane | Dioxete |
| 2× Sulfur | Dithietane | Dithiete |
5-membered rings
Five-membered rings with one heteroatom
| Heteroatom | Saturated | Unsaturated |
|---|---|---|
| Antimony | Stibolane | Stibole |
| Arsenic | Arsolane | Arsole |
| Bismuth | Bismolane | Bismole |
| Boron | Borolane | Borole |
| Nitrogen | Pyrrolidine ("Azolidine" is not used) | Pyrrole ("Azole" is not used) |
| Oxygen | Tetrahydrofuran | Furan |
| Phosphorus | Phospholane | Phosphole |
| Selenium | Selenolane | Selenophene |
| Silicon | Silacyclopentane | Silole |
| Sulfur | Tetrahydrothiophene | Thiophene |
| Tellurium | Tellurophene | |
| Tin | Stannolane | 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.
| Heteroatoms | Saturated | Unsaturated (and partially unsaturated) |
|---|---|---|
| 2× nitrogen | Imidazolidine Pyrazolidine |
Imidazole (Imidazoline) Pyrazole (Pyrazoline) |
| Oxygen + sulfur | 1,3-Oxathiolane 1,2-Oxathiolane |
Oxathiole (Oxathioline) Isoxathiole |
| Nitrogen + Oxygen | Oxazolidine Isoxazolidine |
Oxazole (Oxazoline) Isoxazole |
| Nitrogen + sulfur | Thiazolidine Isothiazolidine |
Thiazole (Thiazoline) Isothiazole |
| 2× oxygen | Dioxolane | |
| 2× sulfur | Dithiolane | Dithiole |
Five-membered rings with at least three heteroatoms
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.
| Heteroatoms | Saturated | Unsaturated |
|---|---|---|
| N N N | Triazoles | |
| N N O | Furazan Oxadiazole | |
| N N S | Thiadiazole | |
| N O O | Dioxazole | |
| N S S | Dithiazole | |
| N N N N | Tetrazole | |
| N N N N O | Oxatetrazole | |
| N N N N S | Thiatetrazole | |
| N N N N N | Pentazole |
6-membered rings
Six-membered rings with one heteroatom
| Heteroatom | Saturated | Unsaturated | Ions |
|---|---|---|---|
| Antimony | Stibinin | ||
| Arsenic | Arsinane | Arsinine | |
| Bismuth | Bismin | ||
| Boron | Borinane | Borinine | Boratabenzene anion |
| Germanium | Germinane | Germine | |
| Nitrogen | Piperidine (Azinane is not used) |
Azine is not used) | Pyridinium cation |
| Oxygen | Oxane | Pyran (2H-Oxine is not used) |
Pyrylium cation |
| Phosphorus | Phosphinane | Phosphinine | |
| Selenium | Selenane | Selenopyran | Selenopyrylium cation |
| Silicon | Silinane | Siline | |
| Sulfur | Thiane | Thiopyran (2H-Thiine is not used) |
Thiopyrylium cation |
| Tellurium | Tellurane | Telluropyran | Telluropyrylium cation |
| Tin | Stanninane | Stannine |
Six-membered rings with two heteroatoms
| Heteroatom | Saturated | Unsaturated |
|---|---|---|
| Nitrogen / nitrogen | Diazinane | Diazine |
| Oxygen / nitrogen | Morpholine | Oxazine |
| Sulfur / nitrogen | Thiomorpholine | Thiazine |
| Oxygen / Sulfur | Oxathiane | Oxathiin |
| Oxygen / oxygen | Dioxane | Dioxine |
| Sulfur / sulfur | Dithiane | Dithiin |
| Boron / nitrogen | 1,2-Dihydro-1,2-azaborine |
Six-membered rings with three heteroatoms
| Heteroatom | Saturated | Unsaturated |
|---|---|---|
| Nitrogen | Triazinane | Triazine |
| Oxygen | Trioxane | |
| Sulfur | Trithiane |
Six-membered rings with four heteroatoms
| 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
| Heteroatom | Saturated | Unsaturated |
|---|---|---|
| Nitrogen | Pentazine |
Six-membered rings with six heteroatoms
The hypothetical chemical compound with six nitrogen heteroatoms would be hexazine.
Borazine is a six-membered ring with three nitrogen heteroatoms and three boron heteroatoms.
7-membered rings
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:
| Heteroatom | Saturated | Unsaturated |
|---|---|---|
| Boron | Borepin | |
| Nitrogen | Azepane | Azepine |
| Oxygen | Oxepane | Oxepine |
| Sulfur | Thiepane | Thiepine |
Those with two heteroatoms include:
| Heteroatom | Saturated | Unsaturated |
|---|---|---|
| Nitrogen | Diazepane | Diazepine |
| Nitrogen/sulfur | Thiazepine |
8-membered rings
| 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
| Heteroatom | Saturated | Unsaturated |
|---|---|---|
| Nitrogen | Azonane | Azonine |
| Oxygen | Oxonane | Oxonine |
| Sulfur | Thionane | Thionine |