Hydroxylamine

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Hydroxylamine
Stereo, skeletal formula of hydroxylamine with all explicit hydrogens added Hydroxylamine-2D.png
Stereo, skeletal formula of hydroxylamine with all explicit hydrogens added
Ball-and-stick model of hydroxylamine Hydroxylamine-3D-balls.png
Ball-and-stick model of hydroxylamine
Hydroxylamine-dimensions-2D.png
Names
IUPAC name
Azinous acid
Preferred IUPAC name
Hydroxylamine (only preselected [1] )
Other names
  • Aminol
  • Azanol
  • Hydroxyammonia
  • Hydroxyamine
  • Hydroxyazane
  • Hydroxylazane
  • Nitrinous acid
Identifiers
3D model (JSmol)
3DMet
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.029.327 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 232-259-2
478
KEGG
MeSH Hydroxylamine
PubChem CID
RTECS number
  • NC2975000
UNII
  • InChI=1S/H3NO/c1-2/h2H,1H2 Yes check.svgY
    Key: AVXURJPOCDRRFD-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/H3NO/c1-2/h2H,1H2
    Key: AVXURJPOCDRRFD-UHFFFAOYAD
  • NO
Properties
NH2OH
Molar mass 33.030 g·mol−1
AppearanceVivid white, opaque crystals
Density 1.21 g cm−3 (at 20 °C) [2]
Melting point 33 °C (91 °F; 306 K)
Boiling point 58 °C (136 °F; 331 K) /22 mm Hg (decomposes)
Soluble
log P −0.758
Acidity (pKa)6.03 ([NH3OH]+)
Basicity (pKb)7.97
Structure
Tricoordinated at N, dicoordinated at O
Trigonal pyramidal at N, bent at O
0.67553 D
Thermochemistry
46.47 J/(K·mol)
Std molar
entropy
(S298)
236.18 J/(K·mol)
−39.9 kJ/mol
Hazards
GHS labelling:
GHS-pictogram-explos.svg GHS-pictogram-acid.svg GHS-pictogram-exclam.svg GHS-pictogram-silhouette.svg GHS-pictogram-pollu.svg
Danger
H200, H290, H302, H312, H315, H317, H318, H335, H351, H373, H400
P201, P202, P234, P260, P261, P264, P270, P271, P272, P273, P280, P281, P301+P312, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P312, P314, P321, P322, P330, P332+P313, P333+P313, P362, P363, P372, P373, P380, P390, P391, P401, P403+P233, P404, P405, P501
NFPA 704 (fire diamond)
NFPA 704.svgHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 1: Must be pre-heated before ignition can occur. Flash point over 93 °C (200 °F). E.g. canola oilInstability 3: Capable of detonation or explosive decomposition but requires a strong initiating source, must be heated under confinement before initiation, reacts explosively with water, or will detonate if severely shocked. E.g. hydrogen peroxideSpecial hazards (white): no code
2
1
3
Flash point 129 °C (264 °F; 402 K)
265 °C (509 °F; 538 K)
Lethal dose or concentration (LD, LC):
408 mg/kg (oral, mouse); 59–70 mg/kg (intraperitoneal mouse, rat); 29 mg/kg (subcutaneous, rat) [3]
Safety data sheet (SDS) ICSC 0661
Related compounds
Related hydroxylammonium salts
Related compounds
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
X mark.svgN  verify  (what is  Yes check.svgYX mark.svgN ?)

Hydroxylamine (also known as hydroxyammonia) is an inorganic compound with the chemical formula N H 2 OH. The compound is in a form of a white hygroscopic crystals. [4] Hydroxylamine is almost always provided and used as an aqueous solution. It is consumed almost exclusively to produce Nylon-6. The oxidation of NH3 to hydroxylamine is a step in biological nitrification. [5]

Contents

History

Hydroxylamine was first prepared as hydroxylammonium chloride in 1865 by the German chemist Wilhelm Clemens Lossen (1838-1906); he reacted tin and hydrochloric acid in the presence of ethyl nitrate. [6] It was first prepared in pure form in 1891 by the Dutch chemist Lobry de Bruyn and by the French chemist Léon Maurice Crismer (1858-1944). [7] [8] The coordination complex ZnCl2(NH2OH)2 (zinc dichloride di(hydroxylamine)), known as Crismer's salt, releases hydroxylamine upon heating. [9]

Production

Hydroxylamine or its salts (salts containing hydroxylammonium cations [NH3OH]+) can be produced via several routes but only two are commercially viable. It is also produced naturally as discussed in a section on biochemistry.

From nitric oxide

NH2OH is mainly produced as its sulfuric acid salt, hydroxylammonium hydrogen sulfate ([NH3OH]+[HSO4]), by the hydrogenation of nitric oxide over platinum catalysts in the presence of sulfuric acid. [10]

2 NO + 3 H2 + 2 H2SO4 → 2 [NH3OH]+[HSO4]

Raschig process

Another route to NH2OH is the Raschig process: aqueous ammonium nitrite is reduced by HSO3 and SO2 at 0 °C to yield a hydroxylamido-N,N-disulfonate anion:

[NH4]+[NO2] + 2 SO2 + NH3 + H2O → 2 [NH4]+ + N(OH)(SO3)2

This anion is then hydrolyzed to give hydroxylammonium sulfate [NH3OH]2SO4:

N(OH)(SO3)2 + H2O → NH(OH)(SO3) + HSO4
2 NH(OH)(SO3) + 2 H2O → [NH3OH]2SO4 + SO2−4

Solid NH2OH can be collected by treatment with liquid ammonia. Ammonium sulfate, [NH4]2SO4, a side-product insoluble in liquid ammonia, is removed by filtration; the liquid ammonia is evaporated to give the desired product. [4] The net reaction is:

2 NO2 + 4 SO2 + 6 H2O + 6 NH3 → 4 SO2−4 + 6 [NH4]+ + 2 NH2OH

A base then frees the hydroxylamine from the salt:

[NH3OH]Cl + NaO(CH2)3CH3 → NH2OH + NaCl + CH3(CH2)3OH [4]

Other methods

Julius Tafel discovered that hydroxylamine hydrochloride or sulfate salts can be produced by electrolytic reduction of nitric acid with HCl or H2SO4 respectively: [11] [12]

HNO3 + 3 H2 → NH2OH + 2 H2O

Hydroxylamine can also be produced by the reduction of nitrous acid or potassium nitrite with bisulfite:

HNO2 + 2 HSO3 → N(OH)(OSO2)2 + H2O → NH(OH)(OSO2) + HSO4
NH(OH)(OSO2) + [H3O]+[NH3OH]+ + HSO4 (100 °C, 1 h)

Hydrochloric acid disproportionates nitromethane to hydroxylamine hydrochloride and carbon monoxide via the hydroxamic acid.[ citation needed ]

A direct production of hydroxylamine from molecular nitrogen is also possible in water plasma. [13]

Reactions

Hydroxylamine reacts with electrophiles, such as alkylating agents, which can attach to either the oxygen or the nitrogen atoms:

R−X + NH2OH → R−O−NH2 + HX
R−X + NH2OH → R−NH−OH + HX

The reaction of NH2OH with an aldehyde or ketone produces an oxime.

R2C=O + [NH3OH]Cl → R2C=N−OH + NaCl + H2O (in NaOH solution)

This reaction is useful in the purification of ketones and aldehydes: if hydroxylamine is added to an aldehyde or ketone in solution, an oxime forms, which generally precipitates from solution; heating the precipitate with an inorganic acid then restores the original aldehyde or ketone. [14]

Oximes such as dimethylglyoxime are also employed as ligands.

NH2OH reacts with chlorosulfonic acid to give hydroxylamine-O-sulfonic acid: [15]

HO−S(=O)2−Cl + NH2OH → NH2−O−S(=O)2−OH + HCl

When heated, hydroxylamine explodes. A detonator can easily explode aqueous solutions concentrated above 80% by weight, and even 50% solution might prove detonable if tested in bulk. [16] [17] In air, the combustion is rapid and complete:

4 NH2OH + O2 → 2 N2 + 6 H2O

Absent air, pure hydroxylamine requires stronger heating and the detonation does not complete combustion:

3 NH2OH → N2 + NH3 + 3 H2O

Partial isomerisation to the amine oxide H3N+−O contributes to the high reactivity. [18]

Functional group

Secondary N,N-hydroxylamine schema Hydroxylamine-group-2D.png
Secondary N,N-hydroxylamine schema

Substituted derivatives of hydroxylamine are known. When the hydroxyl or an amine hydrogen is substituted, such a molecule is called (respectively) an O- or N-hydroxylamine. In general N-hydroxylamines are more common. Examples are N-tert-butylhydroxylamine or the glycosidic bond in calicheamicin. N,O-Dimethylhydroxylamine is a precursor to Weinreb amides.

Similarly to amines, one can distinguish hydroxylamines by their degree of substitution: primary, secondary and tertiary. When stored exposed to air for weeks, secondary hydroxylamines degrade to nitrones. [19]

N-organylhydroxylamines, R−NH−OH, where R is an organyl group, can be reduced to amines R−NH2: [20]

R−NH−OH (Zn, HCl) → R−NH2 + ZnO

Synthesis

Amine oxidation with benzoyl peroxide is the most common method to synthesize hydroxylamines. Care must be taken to prevent over-oxidation to a nitrone. Other methods include:

Uses

Conversion of cyclohexanone to caprolactam involving the Beckmann rearrangement. Beckmann-rearangement.png
Conversion of cyclohexanone to caprolactam involving the Beckmann rearrangement.

Approximately 95% of hydroxylamine is used in the synthesis of cyclohexanone oxime, a precursor to Nylon 6. [10] The treatment of this oxime with acid induces the Beckmann rearrangement to give caprolactam (3). [21] The latter can then undergo a ring-opening polymerization to yield Nylon 6. [22]

Laboratory uses

Hydroxylamine and its salts are commonly used as reducing agents in myriad organic and inorganic reactions. They can also act as antioxidants for fatty acids.

High concentrations of hydroxylamine are used by biologists to introduce mutations by acting as a DNA nucleobase amine-hydroxylating agent. [23] In is thought to mainly act via hydroxylation of cytidine to hydroxyaminocytidine, which is misread as thymidine, thereby inducing C:G to T:A transition mutations. [24] But high concentrations or over-reaction of hydroxylamine in vitro are seemingly able to modify other regions of the DNA & lead to other types of mutations. [24] This may be due to the ability of hydroxylamine to undergo uncontrolled free radical chemistry in the presence of trace metals and oxygen, in fact in the absence of its free radical affects Ernst Freese noted hydroxylamine was unable to induce reversion mutations of its C:G to T:A transition effect & even considered hydroxylamine to be the most specific mutagen known. [25] Practically, it has been largely surpassed by more potent mutagens such as EMS, ENU, or nitrosoguanidine, but being a very small mutagenic compound with high specificity, it found some specialized uses such as mutation of DNA packed within bacteriophage capsids, [26] & mutation of purified DNA in vitro. [27]

This route also involves the Beckmann Rearrangement, like the conversion from cyclohexanone to caprolactam. Celanese synthesis of paracetamol.svg
This route also involves the Beckmann Rearrangement, like the conversion from cyclohexanone to caprolactam.

An alternative industrial synthesis of paracetamol developed by HoechstCelanese involves the conversion of ketone to a ketoxime with hydroxylamine.

Some non-chemical uses include removal of hair from animal hides and photographic developing solutions. [2] In the semiconductor industry, hydroxylamine is often a component in the "resist stripper", which removes photoresist after lithography.

Hydroxylamine can also be used to better characterize the nature of a post-translational modification onto proteins. For example, poly(ADP-Ribose) chains are sensitive to hydroxylamine when attached to glutamic or aspartic acids but not sensitive when attached to serines. [28] Similarly, Ubiquitin molecules bound to serines or threonines residues are sensitive to hydroxylamine, but those bound to lysine (isopeptide bond) are resistant. [29]

Biochemistry

In biological nitrification, the oxidation of NH3 to hydroxylamine is mediated by the ammonia monooxygenase (AMO). [5] Hydroxylamine oxidoreductase (HAO) further oxidizes hydroxylamine to nitrite. [30]

Cytochrome P460, an enzyme found in the ammonia-oxidizing bacteria Nitrosomonas europea , can convert hydroxylamine to nitrous oxide, a potent greenhouse gas. [31]

Hydroxylamine can also be used to highly selectively cleave asparaginyl-glycine peptide bonds in peptides and proteins. [32] It also bonds to and permanently disables (poisons) heme-containing enzymes. It is used as an irreversible inhibitor of the oxygen-evolving complex of photosynthesis on account of its similar structure to water.

Safety and environmental concerns

With a theoretical decomposition energy of about 5 kJ/g, hydroxylamine is an explosive, and aqueous solutions above 80% can be easily detonated by detonator or strong heating under confinement. [16] [17] At least two factories dealing in hydroxylamine have been destroyed since 1999 with loss of life. [33] It is known, however, that ferrous and ferric iron salts accelerate the decomposition of 50% NH2OH solutions. [34] Hydroxylamine and its derivatives are more safely handled in the form of salts.

It is an irritant to the respiratory tract, skin, eyes, and other mucous membranes. It may be absorbed through the skin, is harmful if swallowed, and is a possible mutagen. [35]

See also

Related Research Articles

<span class="mw-page-title-main">Amine</span> Chemical compounds and groups containing nitrogen with a lone pair (:N)

In chemistry, amines are compounds and functional groups that contain a basic nitrogen atom with a lone pair. Amines are formally derivatives of ammonia, wherein one or more hydrogen atoms have been replaced by a substituent such as an alkyl or aryl group. Important amines include amino acids, biogenic amines, trimethylamine, and aniline. Inorganic derivatives of ammonia are also called amines, such as monochloramine.

<span class="mw-page-title-main">Acid–base reaction</span> Chemical reaction between an acid and a base

In chemistry, an acid–base reaction is a chemical reaction that occurs between an acid and a base. It can be used to determine pH via titration. Several theoretical frameworks provide alternative conceptions of the reaction mechanisms and their application in solving related problems; these are called the acid–base theories, for example, Brønsted–Lowry acid–base theory.

<span class="mw-page-title-main">Aldehyde</span> Organic compound containing the functional group R−CH=O

In organic chemistry, an aldehyde is an organic compound containing a functional group with the structure R−CH=O. The functional group itself can be referred to as an aldehyde but can also be classified as a formyl group. Aldehydes are a common motif in many chemicals important in technology and biology.

<span class="mw-page-title-main">Ammonium</span> Chemical compound

The ammonium cation is a positively charged polyatomic ion with the chemical formula NH+4 or [NH4]+. It is formed by the protonation of ammonia. Ammonium is also a general name for positively charged (protonated) substituted amines and quaternary ammonium cations, where one or more hydrogen atoms are replaced by organic or other groups. Not only is ammonium a source of nitrogen and a key metabolite for many living organisms, but it is an integral part of the global nitrogen cycle. As such, the human impact in recent years could have an effect on the biological communities that depend on it.

<span class="mw-page-title-main">Oxime</span> Organic compounds of the form >C=N–OH

In organic chemistry, an oxime is an organic compound belonging to the imines, with the general formula RR’C=N−OH, where R is an organic side-chain and R' may be hydrogen, forming an aldoxime, or another organic group, forming a ketoxime. O-substituted oximes form a closely related family of compounds. Amidoximes are oximes of amides with general structure R1C(=NOH)NR2R3.

<span class="mw-page-title-main">Nitrous acid</span> Chemical compound

Nitrous acid is a weak and monoprotic acid known only in solution, in the gas phase, and in the form of nitrite salts. It was discovered by Carl Wilhelm Scheele, who called it "phlogisticated acid of niter". Nitrous acid is used to make diazonium salts from amines. The resulting diazonium salts are reagents in azo coupling reactions to give azo dyes.

In organic chemistry, a nitrile is any organic compound that has a −C≡N functional group. The name of the compound is composed of a base, which includes the carbon of the −C≡N, suffixed with "nitrile", so for example CH3CH2C≡N is called "propionitrile". The prefix cyano- is used interchangeably with the term nitrile in industrial literature. Nitriles are found in many useful compounds, including methyl cyanoacrylate, used in super glue, and nitrile rubber, a nitrile-containing polymer used in latex-free laboratory and medical gloves. Nitrile rubber is also widely used as automotive and other seals since it is resistant to fuels and oils. Organic compounds containing multiple nitrile groups are known as cyanocarbons.

<span class="mw-page-title-main">Tollens' reagent</span> Chemical reagent used to distinguish between aldehydes and ketones

Tollens' reagent is a chemical reagent used to distinguish between aldehydes and ketones along with some alpha-hydroxy ketones which can tautomerize into aldehydes. The reagent consists of a solution of silver nitrate, ammonium hydroxide and some sodium hydroxide. It was named after its discoverer, the German chemist Bernhard Tollens. A positive test with Tollens' reagent is indicated by the precipitation of elemental silver, often producing a characteristic "silver mirror" on the inner surface of the reaction vessel.

<span class="mw-page-title-main">Hemiaminal</span> Organic compound or group with a hydroxyl and amine attached to the same carbon

In organic chemistry, a hemiaminal is a functional group or type of chemical compound that has a hydroxyl group and an amine attached to the same carbon atom: −C(OH)(NR2)−. R can be hydrogen or an alkyl group. Hemiaminals are intermediates in imine formation from an amine and a carbonyl by alkylimino-de-oxo-bisubstitution. Hemiaminals can be viewed as a blend of aminals and geminal diol. They are a special case of amino alcohols.

<span class="mw-page-title-main">Hexol</span> Chemical compound

In chemistry, hexol is a cation with formula {[Co(NH3)4(OH)2]3Co}6+ — a coordination complex consisting of four cobalt cations in oxidation state +3, twelve ammonia molecules NH
3
, and six hydroxy anions HO
, with a net charge of +6. The hydroxy groups act as bridges between the central cobalt atom and the other three, which carry the ammonia ligands.

<span class="mw-page-title-main">Bisulfite</span> Chemical compound or ion

The bisulfite ion (IUPAC-recommended nomenclature: hydrogensulfite) is the ion HSO
3
. Salts containing the HSO
3
ion are also known as "sulfite lyes". Sodium bisulfite is used interchangeably with sodium metabisulfite (Na2S2O5). Sodium metabisulfite dissolves in water to give a solution of Na+HSO
3
.

<span class="mw-page-title-main">Nitrone</span> Chemical group (>C=N(O)–)

In organic chemistry, a nitrone is a functional group consisting of an N-oxide of an imine. The general structure is R1R2C=N+(−O)(−R3), where R3 is not a hydrogen. Their primary application is intermediates in chemical synthesis. A nitrone is a 1,3-dipole used in cycloadditions, and a carbonyl mimic.

The chemical element nitrogen is one of the most abundant elements in the universe and can form many compounds. It can take several oxidation states; but the most common oxidation states are -3 and +3. Nitrogen can form nitride and nitrate ions. It also forms a part of nitric acid and nitrate salts. Nitrogen compounds also have an important role in organic chemistry, as nitrogen is part of proteins, amino acids and adenosine triphosphate.

Carbamic acid, which might also be called aminoformic acid or aminocarboxylic acid, is the chemical compound with the formula H2NCOOH. It can be obtained by the reaction of ammonia NH3 and carbon dioxide CO2 at very low temperatures, which also yields ammonium carbamate [NH4]+[NH2CO2]. The compound is stable only up to about 250 K (−23 °C); at higher temperatures it decomposes into those two gases. The solid apparently consists of dimers, with the two molecules connected by hydrogen bonds between the two carboxyl groups –COOH.

Hyponitrous acid is a chemical compound with formula H
2
N
2
O
2
or HON=NOH. It is an isomer of nitramide, H2N−NO2; and a formal dimer of azanone, HNO.

<span class="mw-page-title-main">Hydroxylammonium chloride</span> Chemical compound, [NH3OH]Cl

Hydroxylammonium chloride is a chemical compound with the formula [NH3OH]+Cl. It is the hydrochloric acid salt of hydroxylamine. Hydroxylamine is a biological intermediate in nitrification and in anammox which are important in the nitrogen cycle in soil and in wastewater treatment plants.

<span class="mw-page-title-main">Hydroxylammonium sulfate</span> Chemical compound

Hydroxylammonium sulfate [NH3OH]2SO4, is the sulfuric acid salt of hydroxylamine. It is primarily used as an easily handled form of hydroxylamine, which is explosive when pure.

In chemistry, the amino radical, ·NH2, also known as the aminyl radical or azanyl radical, is the neutral form of the amide ion. Aminyl radicals are highly reactive and consequently short-lived, like most radicals; however, they form an important part of nitrogen chemistry. In sufficiently high concentration, amino radicals dimerise to form hydrazine. While NH2 as a functional group is common in nature, forming a part of many compounds, the radical cannot be isolated in its free form.

Hydroxylamine-<i>O</i>-sulfonic acid Chemical compound

Hydroxylamine-O-sulfonic acid (HOSA) or aminosulfuric acid is the inorganic compound with molecular formula H3NO4S that is formed by the sulfonation of hydroxylamine with oleum. It is a white, water-soluble and hygroscopic, solid, commonly represented by the condensed structural formula H2NOSO3H, though it actually exists as a zwitterion and thus is more accurately represented as +H3NOSO3. It is used as a reagent for the introduction of amine groups (–NH2), for the conversion of aldehydes into nitriles and alicyclic ketones into lactams (cyclic amides), and for the synthesis of variety of nitrogen-containing heterocycles.

In chemistry, ammonolysis (/am·mo·nol·y·sis/) is the process of splitting ammonia into . Ammonolysis reactions can be conducted with organic compounds to produce amines (molecules containing a nitrogen atom with a lone pair, :N), or with inorganic compounds to produce nitrides. This reaction is analogous to hydrolysis in which water molecules are split. Similar to water, liquid ammonia also undergoes auto-ionization, , where the rate constant is k = 1.9 × 10-38.

References

  1. "Front Matter". Nomenclature of Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book). Cambridge: The Royal Society of Chemistry. 2014. p. 993. doi:10.1039/9781849733069-FP001 (inactive 2024-04-26). ISBN   978-0-85404-182-4.{{cite book}}: CS1 maint: DOI inactive as of April 2024 (link)
  2. 1 2 Lide, David R., ed. (2006). CRC Handbook of Chemistry and Physics (87th ed.). Boca Raton, FL: CRC Press. ISBN   0-8493-0487-3.
  3. Martel, B.; Cassidy, K. (2004). Chemical Risk Analysis: A Practical Handbook. Butterworth–Heinemann. p. 362. ISBN   978-1-903996-65-2.
  4. 1 2 3 Greenwood and Earnshaw. Chemistry of the Elements. 2nd Edition. Reed Educational and Professional Publishing Ltd. pp. 431–432. 1997.
  5. 1 2 Lawton, Thomas J.; Ham, Jungwha; Sun, Tianlin; Rosenzweig, Amy C. (2014-09-01). "Structural conservation of the B subunit in the ammonia monooxygenase/particulate methane monooxygenase superfamily". Proteins: Structure, Function, and Bioinformatics. 82 (9): 2263–2267. doi:10.1002/prot.24535. ISSN   1097-0134. PMC   4133332 . PMID   24523098.
  6. W. C. Lossen (1865) "Ueber das Hydroxylamine" (On hydroxylamine), Zeitschrift für Chemie, 8 : 551-553. From p. 551: "Ich schlage vor, dieselbe Hydroxylamin oder Oxyammoniak zu nennen." (I propose to call it hydroxylamine or oxyammonia.)
  7. C. A. Lobry de Bruyn (1891) "Sur l'hydroxylamine libre" (On free hydroxylamine), Recueil des travaux chimiques des Pays-Bas, 10 : 100-112.
  8. L. Crismer (1891) "Préparation de l'hydroxylamine cristallisée" (Preparation of crystalized hydroxylamine), Bulletin de la Société chimique de Paris, series 3, 6 : 793-795.
  9. Walker, John E.; Howell, David M. (1967). "Dichlorobis(hydroxylamine)zinc(II) (Crismer's Salt)". Inorganic Syntheses. Vol. 9. pp. 2–3. doi:10.1002/9780470132401.ch2. ISBN   9780470132401.
  10. 1 2 Ritz, Josef; Fuchs, Hugo; Perryman, Howard G. (2000). "Hydroxylamine". Ullmann's Encyclopedia of Industrial Chemistry . Weinheim: Wiley-VCH. doi:10.1002/14356007.a13_527. ISBN   978-3527306732.
  11. James Hale, Arthur (1919). The Manufacture of Chemicals by Electrolysis (1st ed.). New York: D. Van Nostrand Co. p.  32 . Retrieved 5 June 2014. manufacture of chemicals by electrolysis hydroxylamine 32.
  12. Osswald, Philipp; Geisler, Walter (1941). Process of preparing hydroxylamine hydrochloride (US2242477) (PDF). U.S. Patent Office.
  13. Zhang, Xiaoping; Su, Rui; Li, Jingling; Huang, Liping; Yang, Wenwen; Chingin, Konstantin; Balabin, Roman; Wang, Jingjing; Zhang, Xinglei; Zhu, Weifeng; Huang, Keke; Feng, Shouhua; Chen, Huanwen (2024). "Efficient catalyst-free N2 fixation by water radical cations under ambient conditions". Nature Communications . 15 (1) 1535: 1535. doi:10.1038/s41467-024-45832-9. PMC   10879522 . PMID   38378822.
  14. Ralph Lloyd Shriner, Reynold C. Fuson, and Daniel Y. Curtin, The Systematic Identification of Organic Compounds: A Laboratory Manual, 5th ed. (New York: Wiley, 1964), chapter 6.
  15. Wiberg, Egon; Wiberg, Nils (2001). Inorganic Chemistry. Academic Press. pp. 675–677. ISBN   978-0-12-352651-9.
  16. 1 2 Iwata, Yusaku; Koseki, Hiroshi; Hosoya, Fumio (2003-01-01). "Study on decomposition of hydroxylamine/water solution". Journal of Loss Prevention in the Process Industries. 16 (1): 41–53. doi:10.1016/S0950-4230(02)00072-4. ISSN   0950-4230.
  17. 1 2 Bretherick's Handbook of Reactive Chemical Hazards. ISBN   9780081009710 . Retrieved 2023-08-28.
  18. Kirby, AJ; Davies, JE; Fox, DJ; Hodgson, DR; Goeta, AE; Lima, MF; Priebe, JP; Santaballa, JA; Nome, F (28 February 2010). "Ammonia oxide makes up some 20% of an aqueous solution of hydroxylamine". Chemical Communications. 46 (8): 1302–4. doi:10.1039/b923742a. PMID   20449284.
  19. Hamer, Jan; Macaluso, Anthony (1964) [29 Feb 1964]. "Nitrones". Chemical Reviews. 64 (4): 476. doi:10.1021/cr60230a006.
  20. Smith, Michael and Jerry March. March's advanced organic chemistry : reactions, mechanisms, and structure. New York. Wiley. p. 1554. 2001.
  21. Clayden, Jonathan; Greeves, Nick; Warren, Stuart (2012). Organic chemistry (2nd ed.). Oxford University Press. p. 958. ISBN   978-0-19-927029-3.
  22. Nuyken, Oskar; Pask, Stephen (25 April 2013). "Ring-Opening Polymerization—An Introductory Review". Polymers. 5 (2): 361–403. doi: 10.3390/polym5020361 .
  23. Waugh, Robbie; Leader, David J.; McCallum, Nicola; Caldwell, David (2006). "Harvesting the potential of induced biological diversity". Trends in Plant Science. 11 (2). Elsevier BV: 71–79. doi:10.1016/j.tplants.2005.12.007. ISSN   1360-1385. PMID   16406304.
  24. 1 2 Busby, Stephen; Irani, Meher; de Crombrugghe, Benoít (1982). "Isolation of mutant promoters in the Escherichia coli galactose operon using local mutagenesis on cloned DNA fragments". Journal of Molecular Biology. 154 (2). Elsevier BV: 197–209. doi:10.1016/0022-2836(82)90060-2. ISSN   0022-2836. PMID   7042980.
  25. Hollaender, Alexander (1971). Chemical Mutagens : Principles and Methods for Their Detection Volume 1. Boston, MA: Springer US. p. 41. ISBN   978-1-4615-8968-6. OCLC   851813793.
  26. Hong, J.-S.; Ames, B. N. (1971-12-01). "Localized Mutagenesis of Any Specific Small Region of the Bacterial Chromosome". Proceedings of the National Academy of Sciences. 68 (12): 3158–3162. Bibcode:1971PNAS...68.3158H. doi: 10.1073/pnas.68.12.3158 . ISSN   0027-8424. PMC   389612 . PMID   4943557.
  27. Forsberg, Susan. "Hydroxylamine Mutagenesis of plasmid DNA". PombeNet. University of Southern California. Retrieved 9 December 2021.
  28. Langelier, Marie-France; Billur, Ramya; Sverzhinsky, Aleksandr; Black, Ben E.; Pascal, John M. (2021-11-18). "HPF1 dynamically controls the PARP1/2 balance between initiating and elongating ADP-ribose modifications". Nature Communications. 12 (1): 6675. Bibcode:2021NatCo..12.6675L. doi:10.1038/s41467-021-27043-8. ISSN   2041-1723. PMC   8602370 . PMID   34795260.
  29. Kelsall, Ian R.; Zhang, Jiazhen; Knebel, Axel; Arthur, J. Simon C.; Cohen, Philip (2019-07-02). "The E3 ligase HOIL-1 catalyses ester bond formation between ubiquitin and components of the Myddosome in mammalian cells". Proceedings of the National Academy of Sciences. 116 (27): 13293–13298. Bibcode:2019PNAS..11613293K. doi: 10.1073/pnas.1905873116 . ISSN   0027-8424. PMC   6613137 . PMID   31209050.
  30. Arciero, David M.; Hooper, Alan B.; Cai, Mengli; Timkovich, Russell (1993-09-01). "Evidence for the structure of the active site heme P460 in hydroxylamine oxidoreductase of Nitrosomonas". Biochemistry. 32 (36): 9370–9378. doi:10.1021/bi00087a016. ISSN   0006-2960. PMID   8369308.
  31. Caranto, Jonathan D.; Vilbert, Avery C.; Lancaster, Kyle M. (2016-12-20). "Nitrosomonas europaea cytochrome P460 is a direct link between nitrification and nitrous oxide emission". Proceedings of the National Academy of Sciences. 113 (51): 14704–14709. Bibcode:2016PNAS..11314704C. doi: 10.1073/pnas.1611051113 . ISSN   0027-8424. PMC   5187719 . PMID   27856762.
  32. Bornstein, Paul; Balian, Gary (1977). "Cleavage at AsnGly bonds with hydroxylamine". Enzyme Structure Part E. Methods in Enzymology. Vol. 47(Enzyme Struct., Part E). pp. 132–45. doi:10.1016/0076-6879(77)47016-2. ISBN   978-0-12-181947-7. PMID   927171.{{cite book}}: CS1 maint: multiple names: authors list (link)
  33. Japan Science and Technology Agency Failure Knowledge Database Archived 2007-12-20 at the Wayback Machine .
  34. Cisneros, L. O.; Rogers, W. J.; Mannan, M. S.; Li, X.; Koseki, H. (2003). "Effect of Iron Ion in the Thermal Decomposition of 50 mass% Hydroxylamine/Water Solutions". J. Chem. Eng. Data. 48 (5): 1164–1169. doi:10.1021/je030121p.
  35. MSDS Sigma-Aldrich

Further reading