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Sulfur, Selenium and Tellurium

Quick move to entries starting with the letters E, H, I, M, P, Se, Sulfa, Sulfe, Sulfi, Sulfo, Sulfu,
T or X.

dithioacetals:* See thioacetals.

episulfonium ions:
Ions derived from thiiranes, in which a trivalent sulfur atom bears a positive charge:
hydrocarbylsulfanyl nitrenes:
Nitrenes substituted with hydrocarbylsulfanyl groups, RS-N: RS+=N- RSN. Sulfenyl nitrenes is a
older synonymous term. E.g. MeSN methylsulfanylnitrene or methylthionitrene. The
synonymous term thiazynes (from the third canonical form; confusable with the hetarynes
derivable from 1,2- and 1,4-thiazine) is best avoided.
hydropolysulfides:*
Compounds having the structures RS H, RS H...RSnH, in which Sn is a chain of sulfur atoms, and
2 3

R is hydrocarbyl. NOC Rule C-513.1. GNOC Recom. R-5.5.6. Some people exclude
hydrodisulfides from the class hydropolysulfides.
hydrosulfides: Term used in radicofunctional nomenclature of thiols. NOC C-511.5.
Hydrosulfides is not commonly used as a class name for thiols.
isoselenocyanates:*
Selenium analogues of isocyanates: RN=C=Se. NOC Rule C-833.1.
isothiocyanates:*
Sulfur analogues of isocyanates: RN=C=S. NOC Rule C-833.1.
mercaptals:
A term once used for dithioacetals derived from aldehydes; its use is discouraged. NOC Rule C-
533.1, footnote. See thioacetals.
mercaptans:
A traditional term abandoned by IUPAC, synonymous with thiols. NOC Rule C-511, footnote.
This term is still widely used.
mercaptides: An obsolescent synonym for thiolates.
mercaptoles:
An archaic term for dithioketals. NOC Rule C-533.1, footnote. See thioacetals.
monothioacetals:* See thioacetals.
mustard oils: An archaic term for isothiocyanates, RN=C=S.
polysulfanes:*
Compounds having an unbranched chain of sulfur atoms (S or higher) terminating in H: HSnH.
2

NOC Rule C-515.2. GNOC Recom. R-5.5.6. Some chemists exclude disulfane, HS H, from the
2

class polysulfanes.
polysulfides:*
Compounds R-[S]n-R, with a chain of sulfur atoms (n greater than 1) and R not equal to H. NOC
Rule C-515. GNOC Recom. R-5.5.6. Some chemists exclude disulfides, RS R, from the class
2

polysulfides.
selenenic acids:*
Compounds having the structure RSeOH (R not equal to H). NOC Rule C-701. E.g. ArSeOH,
areneselenenic acids.
selenides:*
1. Compounds having the structure RSeR (R not equal to H). They are thus selenium analogues
of ethers. NOC Rule C-701.1.
2. Metal salts of selane, H Se.
2

seleninic acids:*
Compounds having the structure RSe(=O)OH. NOC Rule C-701.
selenocyanates:*
Salts and esters of selenocyanic acid, HSeCN. NOC Rule C-833.1. E.g. CH CH SeCN ethyl
3 2

selenocyanate.
selenols:*
Compounds having the structure RSeH (R not equal to H). NOC Rule C-701.
selenones:*
Compounds having the structure R Se(=O) . NOC Rule C-701.
2 2
selenonic acids:*
Compounds having the structure RSe(=O) OH. NOC Rule C-701.
2

selenoxides:*
Compounds having the structure R Se=O (R not equal to H). NOC Rule C-701.
2

selones:*
Compounds having the structure R C=Se (R not equal to H). They are thus selenium analogues of
2

ketones. NOC Rule C-701.

sulfamic acids:*
H NS(=O) OH (sulfamic acid) and its N-hydrocarbyl derivatives. NOC Rule C-661.2. Sulfamic
2 2

acid is called sulfamidic acid in inorganic chemistry.

sulfanes:
A term including hydropolysulfides, polysulfanes, polysulfides. Use is discouraged because of
confusion with the newer systematic name sulfane, H S, and the numerous names derived
2

therefrom.
sulfenamides:*
Compounds derived from sulfenic acids, RSOH (R not equal to H), by replacement of -OH by
-NR . NOC Rule C-641.8. May alternatively be considered as alkylsulfanylamines. E.g.
2

C H SNH ethanesulfenamide or ethylsulfanylamine.

2 5 2

sulfenes:
S,S-Dioxides of thioaldehydes and thioketones, R C=SO .
2 2

sulfenic acids:*
Compounds having the structure RSOH (R not equal to H). NOC Rule C-521.1. E.g. PhSOH
benzenesulfenic acid.
sulfenium ions:
A term sometimes erroneously used for sulfenylium ions.
sulfenyl groups:*
Groups having the structure RS- (R not equal to H). This term is derived from sulfenic acids.
NOC Rule C-641.7.The synonymous term alkylsulfanyl groups is derived from sulfane, H S. 2

GNOC Recom. R-5.5.2. E.g. CH -S- methanesulfenyl, methylthio or methylsulfanyl. NOC Rule
3

C-641.6.
sulfenyl nitrenes: See hydrocarbylsulfanyl nitrenes.
sulfenyl radicals:*
Sulfur-centered radicals having the structure RS. (R not equal to H). This term is derived from
sulfenic acids. The synonymous term hydrocarbylsulfanyl radicals is derived from sulfane, H S.
2

NOC Rule C-81.1. GNOC Recom. R-5.8.1.3. RNRI Rule RC-81.2.5. E.g. CH S. methylsulfanyl
3

or methanesulfenyl radical. An older synonymous term is alkylthio radical. NOC Rule C-81.1.
sulfenylium ions:*
Cations having the structure RS+ (R not equal to H). This term is derived from sulfenic acids.
The synonymous term hydrocarbylsulfanylium ions is derived from sulfane, H S. NOC Rule C-
2
83.1. GNOC Recom. R-5.8.2. RNRI Rule RC-82.2.3.4. E.g. CH S+ methylsulfanylium or
3

methanesulfenylium ion.
sulfides:*
1. Compounds having the structure RSR (R not equal to H). Such compounds were once called
thioethers. NOC Rule C-514.1. See also thioacetals.
2. In an inorganic sense, salts or other derivatives of hydrogen sulfide.
3. A term used in additive nomenclature, see imides (2).
sulfilimines: See sulfimides (1).
sulfimides:*
1. H S=NH, sulfimide, and its hydrocarbyl derivatives. NOC Rule C-633.1. (Indexed by
2

Chemical Abstracts Service under the heading sulfilimine.) They are thus related to sulfoxides in
the same way that imines are related to aldehydes or ketones. E.g. (C H ) S=NPh S,S-diethyl-N
2 5 2

-phenylsulfimide.
2. A term used in Chemical Abstracts Service Index Nomenclature for sulfonylamines,
RN=S(=O) . 2

sulfimines: A non-recommended synonym for sulfimides (1).

sulfinamides:*
Amides of sulfinic acids, RS(=O)OH; thus RS(=O)NR . NOC Rule C-641.8. See also amides.
2

E.g. PhS(=O)NHCH N-methylbenzenesulfinamide.

3

sulfinamidines:*
Amidines of sulfinic acids, RS(=O)OH; thus RS(=NR)NR . NOC Rule C-641.9. E.g.
2

PhS(=NH)NH benzenesulfinamidine
2

sulfines:
S-Oxides of thioaldehydes and thioketones. Not recommended because in English the -ine
termination should be reserved for amines, imines, etc. E.g. PhC(=S=O)H thiobenzaldehyde S-
oxide.
sulfinic acids:*
HS(=O)OH, sulfinic acid, and its S-hydrocarbyl derivatives. NOC Rule C-641. E.g.
(CH ) CHS(=O)OH propane-2-sulfinic acid.
3 2

sulfinic anhydrides:*
Compounds having the structure RS(=O)OS(=O)R. See also acid anhydrides. NOC Rule C-
643.1.
sulfinimines: An obsolescent term for sulfimides (1).
sulfinylamines:*
Compounds having the structure RN=S=O. NOC Rule C-661.5. Formerly called thionylamines.
sulfonamides:*
Amides of sulfonic acids: RS(=O) NR' . NOC Rule C-821.1. E.g. PhS(=O) NHCH N-
2 2 2 3

methylbenzenesulfonamide.
sulfonamidines:
A term abandoned because of its ambiguous use to mean either RS(=O)(=NH)NH 2

(sulfonimidamide) or RS(=NH) NH (sulfonodiimidamide). NOC Rule C-641.9 note.

2 2

sulfones:*
Compounds having the structure, RS(=O) R (R not equal to H). NOC Rule C-631.1. GNOC
2

Recom. R-5.5.7. E.g. C H S(=O) CH ethyl methyl sulfone.

2 5 2 3

sulfonediimines:
Compounds having the structure, RS(=NR) R, formally derived from sulfones by replacing (=O)
2 2

by (=NR) . S. Oae and N. Furukawa, Sulfilimines and Related Derivatives, American Chemical
2

Society, 1983, pp. 1-4. E.g. Ph S(=NH) diphenyl sulfonediimine.

2 2

sulfonic acids:*
HS(=O) OH, sulfonic acid, and its S-hydrocarbyl derivatives. NOC Rule C-641.
2

sulfonic anhydrides:*
Compounds having the structure RS(=O) OS(=O) R'. See also acid anhydrides. NOC rule C-
2 2

643.1. E.g. PhS(=O) OS(=O) Ph benzenesulfonic anhydride.

2 2

sulfonimides: A seldom used synonym of sulfoximides; its use is discouraged.

sulfonium compounds:*
Compounds having the structure R S+ and associated anion (generally, but not necessarily, all
3

three R groups are hydrocarbyl). NOC Rule C-551.1. See under onium compounds. E.g.
[(CH ) S]+ Cl- trimethylsulfonium chloride, 1-thioniabicyclo[2.2.1]heptane bromide.
3 3

sulfonphthaleins:
3,3-Bis(hydroxyaryl)-3H-2,1-benzoxathiole S,S-dioxides, formed by condensation of o-
sulfobenzoic acid with phenols or related compounds. Cf. phthaleins. E.g.
sulfonylamines:*
Compounds having the structure RN=S(=O) . NOC Rule C-661.5. (Indexed by Chemical
2

Abstracts Service at the heading sulfimide.) E.g. CH N=S(=O) N-sulfonylmethylamine. 3 2

sulfoxides:*
Compounds having the structure R S=O (R not equal to H). NOC Rule C-631.1. GNOC Recom.
2

R-5.5.7. E.g. Ph S=O diphenyl sulfoxide.

2

sulfoximides:*
Compounds having the structure R S(=O)=NR. NOC Rule C-633.1. (Indexed by Chemical
2

Abstracts Service at the heading sulfoximines). E.g. (CH ) S(=O)=NPh S,S-dimethyl- N- 3 2

phenylsulfoximide.
sulfoximines: See sulfoximides.
sulfur diimides:
The parent compound HN=S=NH and hydrocarbyl derivatives.
sultams:*
Sulfonamides in which the S-N bond is part of a ring. NOC Rule C-671.2.
sultims:
Tautomeric forms of sultams, having a sulfur-nitrogen double bond as part of a ring.

sultines:
Intramolecular cyclic esters of hydroxy sulfinic acids. (Named by supposed analogy with
lactones and sultones; but the -ine ending is unfortunate.) Cf. sulfinic acids.

sultones:*
Intramolecular cyclic esters of hydroxy sulfonic acids, analogous to lactones. NOC Rule C-
671.1. Cf. sulfonic acids.

tellurides:*
1. Compounds having the structure RTeR (R not equal to H). Thus tellurium analogues of ethers.
NOC Rule C-701.2.
2. Metal salts of tellurane, H Te.
2

tellurones:
Compounds having the structure R Te(=O) . Thus tellurium analogues of sulfones. NOC Rule C-
2 2

701.2.
thiazynes: See hydrocarbylsulfanyl nitrenes.
thio:
This prefix properly denotes replacement of an oxygen by a sulfur. NOC Rule C-502. E.g.
PhC(=S)NH , thiobenzamide. Cf. entries thioacetals to thioketones.
2

thioacetals:*
A term including monothioacetals having the structure R C(OR')(SR') (subclass monothioketals,
2

R not equal to H); and dithioacetals having the structure R C(SR') (subclass dithioketals, R not
2 2

equal to H, R' not equal to H). NOC Rule C-533.1. GNOC Recom. R-5.6.4.1. See also
thiohemiacetals .
thioaldehydes:*
Compounds in which the oxygen of an aldehyde has been replaced by divalent sulfur, RC(=S)H.
NOC Rule C-531. E.g. CH CH C(=S)H propanethial.
3 2

thioaldehyde S-oxides:
Compounds having the structure RC(=S=O)H. NOC Rule C-633.2. (Also known by the
disapproved term sulfines which includes thioaldehyde S-oxides and thioketone S-oxides).
thioanhydrides:*
Compounds having the structure acyl-S-acyl. NOC Rules C-543.5, C-643.2. Also called
diacylsulfanes. GNOC Recom. R-5.7.7.3. E.g. CH C(=O)SC(=S)CH CH acetic thiopropanoic
3 2 3

thioanhydride. See acyl groups.

thiocarboxylic acids:*
Compounds in which one or both oxygens of a carboxy group have been replaced by divalent
sulfur: RC(=O)SH or RC(=S)OH monothiocarboxylic acids, RC(=S)SH dithiocarboxylic acids.
NOC Rule C-541.1.
thiocyanates:*
Salts and esters of thiocyanic acid HSCN. See isothiocyanates. NOC Rule C-833.1. E.g. CH 3

SCN methyl thiocyanate.

thioethers: Former name for sulfides RSR (R not equal to H). NOC Rule C-514.1, footnote.
thiohemiacetals:*
Compounds of structure R C(SR')OH or R C(OR')SH (monothiohemiacetals), or R C(SR')SH
2 2 2

(dithiohemiacetals), R' not equal to H. NOC Rule C-533.2.

thioketones:*
Compounds in which the oxygen of a ketone has been replaced by divalent sulfur: R C=S (R not
2

equal to H). NOC Rule C-532.2. E.g. CH C(=S)CH CH butane-2-thione.

3 2 3

thioketone S-oxides:
Compounds having the structure R C=S=O (R not equal to H). NOC Rule C-633.2. (Also known
2

by the disapproved term sulfines which comprises thioaldehyde S-oxides and thioketone S-
oxides.)
thiols:*
Compounds having the structure RSH (R not equal to H). Also known by the term mercaptans
(abandoned by IUPAC). NOC Rule C-511.2. E.g. MeCH SH ethanethiol.
2

thiolates:*
Derivatives of thiols, in which a metal (or other cation) replaces the hydrogen attached to sulfur.
NOC Rules C-511.3, C-511.4. E.g. CH S- Na+ sodium methanethiolate.
3

thionylamines: See sulfinylamines.

thiyl radicals:
Synonymous with sulfenyl radicals. Due to inconsistencies in use the term is not recommended.
RNRI Rule RC-81.2.5.
xanthates: See xanthic acids.
xanthic acids: