Nitrogen (two or more N atoms)

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Azines of aldehydes: RCH=NN=CHR.

amide hydrazones: See amidrazones.

amide oximes:*

Compounds having the structure RC(NH₂)=NOH and derivatives formed by substitution; formally the oximes of carboxamides. NOC Rule C-952.

amidines:*

Derivatives of oxoacids R_nE(=O)OH in which the hydroxy group is replaced by an amino group and the oxo group is replaced by =NR. Amidines include carboxamidines, sulfinamidines and phosphinamidines, R₂P(=NR)NR₂. In organic chemistry an unspecified amidine is commonly a carboxamidine. See also carboxamidines, sulfinamidines.

amidium ions:*

Cations formally derived by the addition of one hydron to the N or O atom of an amide and N-hydrocarbyl derivatives thereof. In organic chemistry an unspecified amidium ion is commonly a carboxamidium ion: RC(OH)=N⁺R₂ RC(=O⁺H)NR₂ or RC(=O)N⁺R₃. The term does not imply knowledge concerning the position of the cationic centre. RNRI Rule RC-82.1.2. E.g. PhC(=O)N⁺Me ₃ N,N,N-trimethylbenzamidium.

amidrazones:*

Compounds having the structure RC(=NH)NHNH₂ or RC(NH ₂)=NNH₂, formally derived from carboxylic acids. These tautomers are named hydrazide imides and amide hydrazones, respectively. NOC Rule C-953. Also included are N-hydrocarbyl derivatives.

aminals:

Compounds having two amino groups bonded to the same carbon, R₂C(NR₂)₂. Also called geminal diamines. [The term aminal has also been used, with consequent ambiguity, for -amino ethers (hemiaminal ethers); such use is discouraged.] Cf. hemiaminals.

amine imides:*

Compounds formally derived from the attachment of an amine R₃N to a nitrene RN:. The structure R₃N⁺-N^--R expresses the 1,2-dipolar character of amine imides. They may be named systematically as substituted diazan-2-ium-1-ides. RNRI Rule RC-84.1.1. E.g. Me₃N⁺-N^-Me 1,2,2,2-tetramethyldiazan-2-ium-1-ide or trimethylamine N-methylimide. See also ylides.

amine imines: An undesirable synonym for amine imides. See under imides (2), ylides.

aminonitrenes: An incorrect name for isodiazenes. See under carbene analogues.

ammonium imines:

An undesirable synonym for amine imides. See under ylides.

azamines: See isodiazenes.

azanes:

Saturated acyclic nitrogen hydrides having the general formula N_nH_n+2.

azides:*

1. Compounds bearing the group -N₃, viz. -N=N⁺=N-; usually attached to carbon. NOC Rule C-941.1. E.g. PhN₃ phenyl azide or azidobenzene.

2. Salts of hydrazoic acid, HN₃. E.g. NaN₃ sodium azide.

azimines:

A commonly used but undesirable term for azo imides. (Should not be confused with 'azimino', the name for the bridging group, -N=NNH- . NOC Rule B-15.1.)

azines:*

Condensation products, R₂C=NN=CR₂, of two moles of a carbonyl compound with one mole of hydrazine . NOC Rule C-923.1. See also aldazines and ketazines. (This term should not be confused with the ending -azine appearing in Hantzsch-Widman names for some heterocycles.)

azo compounds:*

Derivatives of diazene (diimide), HN=NH, wherein both hydrogens are substituted by hydrocarbyl groups. NOC Rules C-911, C-912. GNOC Recom. R-5.3.3.1 E.g. PhN=NPh azobenzene or diphenyldiazene.

azo imides:

N-Imides of azo compounds, analogous to azoxy compounds, having a delocalised structure RN=N⁺(R)N^-R RN^-N⁺(R)=NR; commonly but undesirably referred to as azimines. See under dipolar compounds, imides (2), ylides.

azomethine imides:

The 1,3-dipolar N-imides of azomethines having the structure RN^--N⁺(R)=CR₂ RN=N⁺(R)C^-R₂. The term azo ylides, derived from the second resonance form, has also been used. See under imides (2), ylides.

azoxy compounds:*

N-Oxides of azo compounds, of structure RN=N⁺ (O^-)R. NOC Rule C-913. GNOC Recom. R-5.3.3.2. See under dipolar compounds. E.g. PhN=N⁺(O^-)Ph azoxybenzene or diphenyldiazene oxide.

carbodiimides:*

Carbodiimide, HN=C=NH, and its hydrocarbyl derivatives. NOC Rule C-956.

carboxamidines:

Compounds having the structure RC(=NR)NR₂. The term is used as a suffix in systematic nomenclature to denote the -C(=NH)NH₂ group including its carbon atom. NOC Rule C-951.1. E.g. CH₃C(=NH)NH₂ acetamidine, 2-butyl-4,5-dihydroimidazole.

cyanine dyes:

Synthetic dyes with the general formula R₂N[CH=CH]_nCH=N⁺R₂ R₂N⁺=CH[CH=CH]_nNR₂ (n is a small number) in which the nitrogen and part of the conjugated chain usually form part of a heterocyclic system, such as imidazole, pyridine, pyrrole, quinoline and thiazole. E.g.

F. M. Hamer, The Cyanine Dyes and Related Compounds, Interscience, 1964.

Analogues of acyclic carboxylic acid anhydride in which =O has been replaced by =NR and -O- by -NR-: RC(=NR)NRC(=NR)R, N-imidoyl amidines. The name 1,3,5-triazapentadienes, formed in contravention of NOC Rule C-61, is sometimes applied as a class name to diamidides. See imidines .

diazanylidenes: An alternative term for isodiazenes.

1,1-diazenes:

An incorrectly formed name for isodiazenes. Use of this name is discouraged. See also nitrenes.

diazenyl radicals:

Radicals of structure RN=N^..

diazo compounds:

Compounds having the divalent diazo group, =N⁺=N^-, attached to a carbon atom. See also dipolar compounds. E.g. CH₂=N₂ diazomethane.

diazoamino compounds:*

Compounds having the structure RN=N-NR₂ (not all R = H, and one R commonly aryl). See also triazenes. In systematic nomenclature, diazoamino prefixed to the name of RH names the compound RN=NNHR' (R = R'). NOC Rule C-942.2. E.g. PhN=N-NPhMe N-methyldiazoaminobenzene.

diazoates:*

Salts RN=NO^- M⁺ (R commonly aryl) of the compounds RN=NOH, (hydrocarbon)diazohydroxides. NOC Rule C-931.3. E.g. PhN=NO^- K⁺ potassium benzenediazoate. In GNOC Recom. R-5.3.3.4 these compounds are named as hydrocarbyldiazenolates and hydrocarbyldiazenols respectively. E.g. PhN=NOH phenyldiazenol. RN=NO^- M⁺ are also known by the non-IUPAC name diazotates.

diazonium salts:

Compounds of structure RN₂⁺ Y^-, in which R is generally but not necessarily aryl, and the cations of which are usually formulated as RN⁺N. NOC Rule C-931. E.g. PhN⁺N Cl^- benzenediazonium chloride. They may also be named, from the canonical form RN=N⁺, hydrocarbyldiazenylium salts. RNRI Rule RC-82.2.2.3.

diazooxides:

Diazocyclohexadienones, which may also be considered as dipolar diazonio phenoxides, obtained by diazotizing aromatic primary amines having a hydroxy group in an ortho or para position. Also known as diazophenols. See also diazo compounds, phenoxides , quinone diazides.

formamidine disulfides:*

The compound H₂NC(=NH)SSC(=NH)NH₂ and its derivatives formed by substitution at nitrogen. NOC Rule C-951.5.

formazans:*

The parent compound H₂NN=CHN=NH and its derivatives formed by substitution at carbon and/or nitrogen. NOC Rule C-955.1.

hydrazides:*

Compounds derived from oxoacids R_kE(=O)_l(OH)_m (l not equal to 0) by replacing -OH by -NRNR₂ (R groups are commonly H), as in carbohydrazides, RC(=O)NHNH₂, NOC Rule C-921.5, (GNOC Recom. R-5.7.8.4), sulfonohydrazides, RS(=O)₂NHNH₂, (NOC Rule C-641.9); and phosphonic dihydrazides, RP(=O)(NHNH₂)₂.

hydrazide hydrazones: See hydrazidines.

hydrazide imides: See amidrazones.

hydrazidines:*

Compounds, RC(-NHNH₂)=NNH₂, derived from carboxylic acids by replacing -OH by -NHNH₂ (or N-substituted analogues) and =O by =NNH₂ (or substituted analogues). NOC Rule C-954.1. A specific hydrazidine is named as a hydrazide hydrazone. E.g. hexanohydrazide hydrazone.

hydrazines:

Hydrazine (diazane), H₂NNH₂, and its hydrocarbyl derivatives. When one or more substituents are acyl groups, the compound is a hydrazide. NOC Rule C-921. N-Alkylidene derivatives are hydrazones. Cf. azines, hydrazo compounds.

hydrazinylidenes: Synonymous with isodiazenes. RNRI Rule RC-81.1.3.2.

hydrazo compounds:

Compounds containing the divalent hydrazo group, -NHNH-, such as hydrazoarenes (1,2-diarylhydrazines or 1,2-diaryldiazanes, usually with both aryl groups the same) and their N-substituted derivatives: ArNRNRAr. See also hydrazines. NOC Rule C-921.2.

hydrazones:*

Compounds having the structure R₂C=NNR₂, formally derived from aldehydes or ketones by replacing =O by =NNH₂ (or substituted analogues). NOC Rule C-922.

hydrazonic acids:*

Compounds derived from oxoacids R_kE(=O)_l(OH)_m (l not equal to 0) by replacing a double-bonded oxygen atom by =NNR₂ , as in carbohydrazonic acids, RC(OH)=NNH₂ (NOC Rule C-451.1) and sulfonohydrazonic acids, RS(=O)(=NNH₂)OH (GNOC Recom. R-5.7.2.1).

imidoyl nitrenes:

Nitrenes having the structure RC(=NR)N: RC(-N^-R)=N⁺:. See imidoyl carbenes.

isodiazenes:*

Compounds having the structure R₂NN:. R₂N⁺=N^-. GNOC Recom. R-5.3.5. These compounds can also be called diazanylidenes or hydrazinylidenes. RNRI Rule RC-81.1.3.2. They have also been called by the trivial name azamines and the incorrectly formed name 1,1-diazenes. They should not be called aminonitrenes; see under carbenes.

ketazines:

Azines of ketones: R ₂C=NN=CR₂.

nitramines:

Amines substituted at N with a nitro group (a contracted form of N-nitroamines); they are thus amides of nitric acid, and the class is composed of nitramide, O₂NNH₂, and its derivatives formed by substitution.

nitrile imides:

Ylides having the structure RCN⁺-N^--R RC⁺=NN^--R RC^-=N⁺=NR. Also known as nitrile imines or nitrilimines, especially in the German literature. R. Huisgen, in 1,3-Dipolar Cycloaddition Chemistry, A. Padwa, Ed. John Wiley and Sons, 1984, p. 3. See also dipolar compounds, ylides.

nitrile imines: See nitrile imides, imides (2).

nitrilimines: See nitrile imides.

nitrimines:

Compounds having the structure O₂NN=CR₂ (also called N-nitroimines).

nitrolic acids:

Compounds having the structure RC(=NOH)NO₂ .

nitrosamides:

Although this term has, regrettably, been used to mean the N-nitroso derivatives of amides, logically it refers to amides of nitrous acid; the unstable parent compound H₂NNO is, in fact, named nitrosamide, but its derivatives formed by substitution with hydrocarbyl groups are by long custom called nitrosamines. See also nitramines.

nitrosamines:

N-Nitroso amines: compounds of the structure R₂NNO. Compounds RNHNO are not ordinarily isolable, but they, too, are nitrosamines. The name is a contraction of N-nitrosoamine and, as such, does not require the N locant. See also nitrosamides.

nitrosimines:

N-Nitroso imines: O=NN=CR₂.

ortho amides:

Hypothetical compounds having the structure RC(NH₂)₃, and N-substituted derivatives thereof. (R₂N)₄C are generally included, but such use is obsolescent.

quinone diazides:

A potentially confusing term for diazooxides; the presence of an azido group, -N₃, is falsely suggested.

semicarbazones:*

Compounds having the structure R₂C=NNHC(=O)NH₂, formally derived by condensation of aldehydes or ketones with semicarbazide [NH₂NHC(=O)NH₂]. NOC Rule C-982.

semioxamazones:

Compounds having the structure R₂C=NNHC(=O)C(=O)NH₂, formally derived from the condensation of aldehydes or ketones with semioxamazide (the hydrazide of oxamic acid), H₂NNHC(=O)C(=O)NH₂.

triazanes:*

Triazane, NH₂NHNH₂, and its hydrocarbyl derivatives. NOC Rule C-942.

triazenes:*

Triazene, NH₂N=NH, and its hydrocarbyl derivatives. See also diazoamino compounds. NOC Rule C-942.1.

uronium salts:*

Salts of O-hydronated urea, having the structure [HOC(=NH₂)NH₂]⁺ X^- (and O- and N-hydrocarbyl derivatives). NOC Rule C-973.1.

verdazyl radicals:

Relatively stable delocalized radicals, derived from hydrazyl, H₂NN^.H, of the types shown, in particular the six-membered ring:

(R most commonly aryl groups.)