Nitrogen (One atom N only)

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aldimines:*

Imines derived from aldehydes : RCH=NR. GNOC Recom. R-5.4.3. E.g. EtCH=NH, PhCH=NMe.

aldoximes:*

Oximes of aldehydes: RCH=NOH. GNOC Recom. R-5.6.6.1.

alkoxyamines:*

O-Alkyl hydroxylamines (with or without substitution on N) : R'ONR₂ (R' not equal to H). NOC Rules C-841.2, C-841.4.

alkylideneamino carbenes: See under nitrile ylides.

alkylideneaminoxyl radicals:

Radicals having the structure R₂C=N-O^.. Synonymous with iminoxyl radicals.

alkylideneaminyl radicals:

Radicals having the structure R₂C=N^.. Synonymous with iminyl radicals.

amic acids:*

Carbamoyl carboxylic acids, i.e. compounds containing a carboxy and a carboxamide group. E.g. 5-carbamoylnicotinic acid.

Note. In systematic nomenclature replacement of the "-ic" suffix of a dicarboxylic acid by "-amic" is limited to dicarboxylic acids that have a trivial name. NOC C-431. E.g. HOC(=O)CH₂C(=O)NH₂ malonamic acid (2-carbamoylacetic acid).

amides:*

1. Derivatives of oxoacids R_kE(=O)_l(OH)_m (l not equal to 0) in which an acidic hydroxy group has been replaced by an amino or substituted amino group. Chalcogen replacement analogues are called thio-, seleno- and telluro-amides. Compounds having one, two, or three acyl groups on a given nitrogen are generically included and may be designated as primary, secondary and tertiary amides, respectively. See also e.g. carboxamides , lactams, peptides, phosphoramides, sulfonamides. NOC Rule C-821. E.g. PhC(=O)NH₂ benzamide, CH₃S(=O)₂NMe₂ N,N-dimethylmethanesulfonamide, [RC(=O)]₂NH secondary amides (see imides), [RC(=O)]₃N tertiary amides, PhP(=O)(OH)NH₂ phenylphosphonamidic acid.

Note 1. Amides with -NH₂, -NHR, and -NR₂ groups should not be distinguished by means of the terms primary, secondary, and tertiary. NOC Rule C-824, footnote.

Note 2. Derivatives of certain acidic compounds R_nE(OH)_m, where E is not carbon (e.g. sulfenic acids, RSOH, phosphinous acids, R₂POH) having the structure R_nE(NR₂)_m may be named as amides but do not belong to the class amides proper. NOC Rules C-641.8, D-5.21. E.g. CH₃CH₂SNH₂ ethanesulfenamide or ethylsulfanylamine.

2. The term applies also to metal derivatives of ammonia and amines, in which a cation replaces a hydrogen atom on nitrogen. Such compounds are also called azanides. RNRI Rule RC-83.1.5. E.g. LiN(i-Pr)₂ lithium diisopropylamide, synonym lithium diisopropylazanide.

amines:*

Compounds formally derived from ammonia by replacing one, two, or three hydrogen atoms by hydrocarbyl groups, and having the general structures RNH₂ (primary amines), R₂NH (secondary amines), R₃N (tertiary amines). NOC Rule C-811.2.

amine oxides:*

Compounds derived from tertiary amines by the attachment of one oxygen atom to the nitrogen atom: R₃N⁺-O^-. NOC Rule C-843. By extension the term includes the analogous derivatives of primary and secondary amines.

amine ylides: Synonymous with ammonium ylides.

aminimides: An undesirable synonym for amine imides. See under ylides.

aminium ions:

Cations HR₃N⁺ formed by hydronation of an amine R₃N. RNRI Rule RC-81.1.1.2. "Non-quaternary ammonium ions" is a synonymous term. E.g. prolinium, PhN⁺HMe ₂ N,N-dimethylanilinium.

Note. If a class X can be hydronated to Xium ions the class Xium ions commonly includes the derivatives formed by the replacement of the added hydron with a hydrocarbyl group. Aminium ions form an exception, made possible by the availability of the class name ammonium ions. See also onium compounds.

aminiumyl radical ions:

Radicals cations, R₃N^.+, derivable from aminium ions, R₃NH⁺, by removal of a hydrogen atom. Aminiumyl radical ions are, except for H₃N^.+, synonymous with the ammoniumyl radical ions. As the term ammonium is well known, ammoniumyl radical ions is the more desirable class name. Cf. ammoniumyl radical ions. RNRI Rule RC-85-3.1.

amino radicals: A non-IUPAC term for aminyl radicals.

aminooxyl radicals:

A spelling for aminoxyl radicals used in NOC (NOC Rules C-841.2, C-81.1). Aminoxyl radicals is now preferred. RNRI Rule RC-81.2.4.

aminoxides:*

The anion H₂N-O^-, aminoxide, and its N-hydrocarbyl derivatives R₂N-O^-; formally derived from hydroxylamines, R₂NOH, by removing a hydron from the hydroxy group. RNRI Rule RC-83.1.4.1. E.g. (CH₃)₂N-O^- dimethylaminoxide.

aminoxyl radicals:*

Compounds having the structure R₂NO^. R₂N^.+-O^- ; they are radicals derived from hydroxylamines by removal of the hydrogen atom from the hydroxy group, and are in many cases isolable. RNRI Rule RC-81.2.4. The synonymous terms "nitroxyl radicals" and "nitroxides" erroneously suggest the presence of a nitro group; their use is not desirable. E.g. (ClCH₂)N-O^. bis(chloromethyl)aminoxyl.

aminyl oxides: Obsolete term for aminoxyl radicals.

aminyl radicals:*

The nitrogen-centered radical H₂N^., formally derived by the removal of a hydrogen atom from ammonia, and its hydrocarbyl derivatives R₂N^.. NOC Rule C-81.1. RNRI Rule RC-81.1.2.

aminylenes:* See nitrenes.

aminylium ions:* See nitrenium ions.

ammonium compounds: See onium compounds.

ammonium ylides:

1,2-Dipolar compounds of general structure R₃N⁺-C^-R₂. See also ylides.

ammoniumyl radical ions:

H₃N^.+ and its hydrocarbyl derivatives. RNRI RC-85.2. E.g. (CH₃)₃ N^.+ trimethylammoniumyl, PhN^.+H₂ phenylammoniumyl or benzenaminiumyl.

anils:

A term for the subclass of Schiff bases R₂C=NR', where R' = N-phenyl or substituted phenyl group. Thus N-phenyl imines.

anilides:*

1. Compounds derived from oxoacids R_kE(=O)_l(OH) _m (l not equal to 0) by replacing an -OH group by the -NHPh group or derivative formed by ring substitution; N-phenyl amides. NOC Rule C-641.8. See amides. E.g. CH₃C(=O)NHPh acetanilide.

2. Salts formed by replacement of a nitrogen-bound hydron of aniline by a metal or other cation. E.g. NaNHPh sodium anilide.

azinic acids:*

Derivatives of the parent structure H₂N⁺(O^-)OH, (GNOC Recom. R-5.3.2) of which the alkylidene derivatives, R₂C=N⁺(O^-)OH (tautomers of nitroalkanes), are the most commonly encountered. The alkylideneazinic acids are known as nitronic acids or, synonymously as aci-nitro compounds. E.g. CH₂=N⁺(O^-)OH methylideneazinic acid.

azo ylides: See azomethine imides.

azomethines:*

Compounds having the structure RN=CR₂ (R not equal to H). NOC Rule C-815.3. Many consider the term to include the compounds RN=CRH (R not equal to H), thus making azomethines synonymous with Schiff bases. Cf. imines.

azomethine oxides: Synonymous with nitrones.

azomethine ylides:

1,3-Dipolar compounds having the structure R₂C^--N⁺(R)=CR₂ R₂C=N⁺(R)C^-R₂. See also ylides.

azonic acids:*

N-Hydrocarbyl derivatives of the parent structure HN⁺(O^-)(OH)₂. GNOC Recom. R-3.3, Table VII. Cf. phosphonic acids.

carbamates:

Salts or esters of carbamic acid, H₂NC(=O)OH, or of N-substituted carbamic acids: R₂NC(=O)OR', (R' = hydrocarbyl or a cation). The esters are often called urethanes or urethans, a usage that is strictly correct only for the ethyl esters.

carbinolamines: An obsolete term for hemiaminals.

carbonitriles:

In systematic nomenclature, the suffix -carbonitrile is used to name compounds RCN where the suffix includes the carbon atom of the -CN. NOC Rule C-832.2. However carbonitrile is not a class name for nitriles.

carbonyl imides:

1,3-Dipolar compounds having the structure R₂C=O⁺-N^-R R₂C⁺-O-N^-R. See also oxonium ylides (2).

carbonyl imines: An undesirable synonym for carbonyl imides . See under ylides.

carboxamides:*

Amides of carboxylic acids, having the structure RC(=O)NR₂. The term is used as a suffix in systematic name formation to denote the -C(=O)NH₂ group including its carbon atom. NOC Rule C-821.1.

carbylamines: An obsolete term, which should not be used, for isocyanides. NOC Rule C-833.1.

cyanates:*

Salts and esters of cyanic acid, HOCN. NOC Rule C-833.1. E.g. KOCN potassium cyanate, PhOCN phenyl cyanate. Cf. isocyanates.

cyanides:*

Salts and C-organyl derivatives of hydrogen cyanide, HCN. NOC Rule C-831.1. GNOC Recom. R-5.7.9.1. See also isocyanides, nitriles, carbonitriles . E.g. CH₃CN methyl cyanide (acetonitrile), NaCN sodium cyanide, PhC(=O)CN benzoyl cyanide.

cyanohydrins:

Alcohols substituted by a cyano group, most commonly, but not limited to, examples having a cyano and a hydroxy group attached to the same carbon atom, formally derived from aldehydes or ketones by the addition of hydrogen cyanide. An individual cyanohydrin can systematically be named as a hydroxy nitrile. See under halohydrins. E.g. (CH₃)₂C(OH)CN 'acetone cyanohydrin' (2-hydroxy-2-methylpropanenitrile), HOCH₂CH₂CN 'ethylene cyanohydrin' (3-hydroxypropanenitrile).

diacylamines:*

Compounds having two acyl groups substituted on ammonia or a primary amine: acyl-NR-acyl. They are also known as secondary amides and, especially the cyclic examples derived from diacids, as imides. NOC Rule C-826. E.g. [RC(=O)]₂NR, RS(=O) ₂NHC(=O)R.

enamines:

Alkenylamines; by usage the term refers specifically to vinylic amines, which have the structure R₂ NCR=CR₂.

fulminates:*

1. Compounds having the structure RON=C:. NOC Rule C-833.1; GNOC Recom. R-5.9.7.2. So called because fulminic acid (actually HCN⁺-O^- formonitrile oxide) was previously considered to be HON=C:.

2. Salts of fulminic acid. E.g. Na⁺[^-CN⁺-O^-].

hemiaminals:

-Amino alcohols, improperly called carbinolamines (the adducts of ammonia, or of primary or secondary amines to the carbonyl group of aldehydes and ketones): R₂C(OH)(NR₂) . Compounds of structure R₂C(OR')NR₂ (R' not equal to H) are hemiaminal ethers, or -amino ethers. See alcohols, aminals, ethers.

hydroxamic acids:*

Compounds, RC(=O)NHOH, derived from oxoacids R_kE(=O)_l(OH)_m (l not equal to 0) by replacing -OH by -NHOH, and hydrocarbyl derivatives thereof. NOC Rule 451.3. Specific examples are preferably named as N-hydroxy amides. NOC Rules C-841.3, C-841.4; GNOC Recom. R-5.7.1.3.3.

hydroximic acids:*

Compounds derived from oxoacids R_kE(=O)_l (OH)_m (l not equal to 0) by replacing =O by =NOH (=NOR), as in carbohydroximic acids, RC(OH)=NOH, (NOC Rule C-451.1) and sulfonohydroximic acids, RS(=O)(=NOH)OH. GNOC Recom. R-5.7.2.1 Table 14.

hydroxylamines:*

Hydroxylamine, H₂N-OH, and its hydrocarbyl derivatives. NOC Rule C-841. See also hydroxamic acids, oximes.

imides:*

1. Diacyl derivatives of ammonia or primary amines, especially those cyclic compounds derived from diacids. NOC Rule C-827. E.g.

2. In additive nomenclature, in which imide is analogous to oxide, the term is used to name compounds of the type R₃Y⁺-N^-R (Y = N, P) and R₂Z⁺-N^-R (Z = O, S, Se, Te), which are the products of formal attachment of an RN= group to N, P, O, S, Se, Te. E.g. amine imides, azomethine imides.

3. Salts having the anion RN₂-. RNRI Rule RC-83.1.2.1.

imidic acids:*

Compounds derived from oxoacids R_kE(=O)_l(OH)_m (l not equal to 0) by replacing =O by =NR; thus tautomers of amides. In organic chemistry an unspecified imidic acid is generally a carboximidic acid, RC(=NR)OH. NOC Rule C-451.1; GNOC Recom. R-5.7.2. E.g. RS(=NH)₂OH a sulfonodiimidic acid. Cf. imino acids.

imidines:

Analogues of cyclic acid anhydrides in which =O has been replaced by =NR and -O- by -NR-. Cf. diamidides.

imidogens:

A non-IUPAC term for nitrenes used in the Chemical Abstracts Service index nomenclature. RNRI RC-81.1.3.1, footnote.

imidonium ions: A term, which is not recommended, for nitrenium ions. GTPOC

imidoyl carbenes:

Carbenes having the structure RC(=NR)C:-R. Imidoyl is a shortened but imprecise term for carboximidoyl, RC(=NH)-.

imines:*

1. Compounds having the structure RN=CR₂ (R = H, hydrocarbyl). Thus analogues of aldehydes or ketones, having NR doubly bonded to carbon; aldimines have the structure RCH=NR, ketimines have the structure R'₂C=NR (R' not equal to H). Imines include azomethines and Schiff bases. Imine is used as a suffix in systematic nomenclature to denote the C=NH group excluding the carbon atom. NOC Rule C-815.3. GNOC Recom. R-5.4.3. See also azomethines, Schiff bases.

2. An obsolete term for azacycloalkanes.

iminium compounds:*

Salts in which the cation has the structure R₂C=N⁺R₂. Thus N-hydronated imines and their N-substituted derivatives. RNRI Rule RC-82.1.2.1. The synonymous terms imonium compounds and immonium compounds are irregularly formed and should not be used. Cf. quaternary ammonium compounds.

imino acids:

1. An obsolete term, which should not be used, for imidic acids .

2. Any carboxylic acid having an imino substituent, HN=, replacing two hydrogens. A shortened form of imino carboxylic acid.

3. Obsolescent term for azaalkanoic acids and azacycloalkane-2-carboxylic acids. E.g. proline

imino carbenes:

This term systematically means carbenes bearing an imino or N-substituted imino group, RN=, somewhere in the molecule. E.g. R-C:-CH₂C(=NR)R. It is listed here in order to warn against its misuse for alkylideneamino carbenes. Cf. carbenes, nitrile ylides.

iminooxy/iminoxy radicals:

This term has improperly been used for alkylideneaminoxyl radicals, also called iminoxyl radicals: R₂C=N-O^.. Its use is strongly discouraged. Cf. aminoxyl radicals, iminyl radicals.

iminoxyl radicals:*

Synonymous with alkylideneaminoxyl radicals. The term can be regarded as a contraction of iminyloxyl radicals. RNRI RC-81.2.4.

iminyl carbenes: See under nitrile ylides.

iminyl radicals:

Radicals having the structure R₂C=N^. . A contraction of alkaniminyl radicals. A synonymous term is alkylideneaminyl radicals. RNRI Rule RC-81.2.3.1. Cf. aminyl radicals . E.g. MeCH=N^. ethaniminyl.

iminylium ions:

Cations having the structure R₂C=N⁺. A contraction of alkaniminylium ions. Alkylideneaminylium ions is a synonymous term. RNRI Rule RC-82.2.3.3. A subclass of nitrenium ions.

isocyanates:*

The isocyanic acid tautomer, HN=C=O, of cyanic acid, HOCN and its hydrocarbyl derivatives: RN=C=O. NOC Rule C-833.1.

isocyanides:*

The isomer HN⁺C^- of hydrocyanic acid, HCN, and its hydrocarbyl derivatives: RNC (RN⁺ C^-). NOC Rule C-833.1.

isonitriles: An obsolete term, which should not be used, for isocyanides. NOC Rule C-833.1.

isonitroso compounds:

An obsolete term for oximes, based on the fact that compounds with a nitroso group, -N=O, bonded to a -CR₂H group readily tautomerise to oximes.

isoureas:*

The imidic acid tautomer of urea, H₂NC(=NH)OH, and its hydrocarbyl derivatives. NOC Rule C-972.

ketenimines:

Compounds having the structure R₂C=C=NR. Thus imino analogues of ketenes.

ketimines:*

Compounds having the structure R₂C=NR' (R not equal to H). GNOC Recom. R-5.4.3. See imines.

ketoximes:*

Oximes of ketones, R ₂C=NOH (R not equal to H). GNOC Recom. R-5.6.6.1.

lactams:*

Cyclic amides of amino carboxylic acids, having a 1-azacycloalkan-2-one structure, or analogues having unsaturation or heteroatoms replacing one or more carbon atoms of the ring. NOC Rule C-475.1. E.g.

lactims:*

Tautomeric forms of lactams, having an endocyclic carbon-nitrogen double bond. Thus, cyclic carboximidic acids. NOC Rule C-475.1. E.g.

nitrenes:*

1. The neutral compound HN: having univalent nitrogen, and its derivatives RN:. Aminylenes is a recognised but less widely used synonym. RNRI Rule RC-81.1.3.1. NOC Rule C-81.2. Other names that have been used include aminediyls, imidogens, azenes. They may exist in either a singlet or a triplet electronic state (four spin-paired electrons, or two spin-paired and two with parallel spins, respectively). Cf. carbenes. E.g. CH₃N: methylnitrene.

2. Until the 1960s, nitrenes had a totally different meaning: analogues of nitrones in which the double-bonded oxygen is replaced by double-bonded carbon, thus azomethine ylides.

nitrenium ions:*

The cation H₂N:⁺ and its N-hydrocarbyl derivatives R₂N:⁺, in which the nitrogen has a positive charge, and two unshared electrons. A synonymous but less widely used term is aminylium ions. RNRI Rule RC-82.2.2.2. The alkylidene derivatives of H₂N:⁺ , R₂C=N:⁺ , still belong to the class nitrenium ions, but are more precisely designated by the term iminylium ions .

nitriles:*

Compounds having the structure RCN; thus C-substituted derivatives of hydrocyanic acid, HCN. NOC Rule C-831. In systematic nomenclature, the suffix nitrile denotes the triply bound N atom, not the carbon atom attached to it. NOC Rule C-832.1. GNOC Recom. R-5.7.9.1. See also, carbonitriles, cyanides, isocyanides.

nitrile oxides:*

Ylides having the structure RCN⁺-O^- RC^-=N⁺=O. NOC Rule C-834.1. See also dipolar compounds.

nitrile sulfides:

Sulfur analogues of nitrile oxides: RCN⁺-S^- RC^-=N⁺=S. See also dipolar compounds.

nitrile ylides:

1,3-Dipolar compounds having the structure RCN⁺-C^-R₂ RC^-=N⁺=CR₂ RC⁺=NC^-R₂ RC:-N=CR₂. The uncharged canonical form C:-N=CR₂ is called an alkylidene- (or hydrocarbylidene-) amino carbene; the name iminyl carbene is incorrect because iminyl is not a recognised prefix for -N=CR₂. See also carbenes, dipolar compounds.

nitrilium betaines:

Derivatives of nitriles having the general structure R-CN⁺-Y^-. A subclass of 1,3-dipolar compounds including nitrile imides, nitrile oxides, nitrile sulfides and nitrile ylides.

nitrilium ions:*

Cations derived formally by attachment of one hydron to the nitrogen atom of a nitrile and hydrocarbyl derivatives thereof. E.g. PhCN⁺H PhC⁺=NH benzonitrilium. RNRI Rule RC-82.1.2.1.

nitro compounds:*

Compounds having the nitro group, -NO₂ (free valence on nitrogen), which may be attached to carbon, nitrogen (as in nitramines), or oxygen (as in nitrates), among other elements (in the absence of specification, C-nitro compounds are usually implied). NOC Rule C-852.1. See also dipolar compounds.

aci-nitro compounds:

A class name for hydrocarbylideneazinic acids, R₂C=N⁺(-O^-)OH. The use of aci-nitro as a prefix in systematic nomenclature to name specific compounds (NOC Rule C-852.2) is abandoned. GNOC Recom. R-5.3.2, footnote. See also azinic acids.

nitrogen mustards: See mustards.

nitrogen ylides: See ylides.

nitrones:*

The N-oxides of imines, that have the structure R₂C=N⁺(O^-)R' (R' not equal to H). NOC Rule C-842.3. Synonymous with azomethine oxides. N-Oxides R₂C=N⁺(O^-)H may be included. See also dipolar compounds.

nitronic acids: See azinic acids.

nitroso compounds:*

Compounds having the nitroso group, -NO, attached to carbon, or to another element, most commonly nitrogen or oxygen. See nitrosamines. NOC Rule C-851.

nitrosolic acids:

Compounds having the structure RC(=NOH)NO.

nitroxides:

Nitroxide is the parent name used by Chemical Abstracts Service for H₂N-O^.. E.g. (ClCH₂)₂N-O^. bis(chloromethyl) nitroxide. The IUPAC name is bis(chloromethyl)aminoxyl. Nitroxides should not be used as a class name for aminoxyl radicals. See aminoxyl radicals.

nitroxyl radicals: See aminoxyl radicals.

oxime O-ethers:*

O-Hydrocarbyl oximes R₂C=NOR' (R' not equal to H). NOC Rule C-842.2.

oximes:*

Compounds of structure R₂C=NOH derived from condensation of aldehydes or ketones with hydroxylamine. NOC Rule C-842.1. GNOC Recom. R-5.6.6.1. Oximes from aldehydes may be called aldoximes; those from ketones may be called ketoximes.

pseudoureas: An obsolescent synonym for isoureas.

quaternary ammonium compounds:*

Derivatives of ammonium compounds, NH₄⁺ Y^-, in which all four of the hydrogens bonded to nitrogen have been replaced with hydrocarbyl groups. Compounds having a carbon-nitrogen double bond (i.e. R₂C=N⁺R₂ Y^-) are more accurately called iminium compounds. See under onium compounds. E.g. [(CH₃)₄N]⁺ OH^- tetramethylammonium hydroxide.

quinonimines/quinone imines:*

Imines derived from quinones by replacement of one or both oxygens by =NR. The term may include both types unless the infix mono or di is included. NOC Rule C-815.3 E.g.o-benzoquinone diimine

quinonoximes:

Mono- or dioximes of quinones; quinone monooximes are tautomeric with nitrosophenols. Cf. oximes.

Schiff bases, Schiff's bases:*

Imines bearing a hydrocarbyl group on the nitrogen atom: R ₂C=NR' (R' not equal to H). NOC Rule C-815.3. Considered by many to be synonymous with azomethines. See also azomethines.

ureides:*

N-Acyl or N,N'-diacyl ureas. NOC Rule C-971.2.

urethanes (urethans):

An alternative term for the compounds R₂NC(=O)OR' (R' not equal to H), esters of carbamic acids, R₂NC(=O)OH, in strict use limited to the ethyl esters, but widely used in the general sense. E.g. 'polyurethane resins'. Cf. carbamates

ynamines:

N,N-Disubstituted alk-1-yn-1-amines, RCCNR₂. By usage, restricted to this type of acetylenic amine. Cf. enamines.