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 (S⦵298)
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 HSO−3 and SO2 at 0 °C to yield a hydroxylamido-N,N-disulfonate anion:

[NH4]+[NO2]− + 2 SO2 + NH3 + H2O → 2 [NH4]+ + N(OH)(SO−3)2

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

N(OH)(SO−3)2 + H2O → NH(OH)(SO−3) + HSO−4
2 NH(OH)(SO−3) + 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 NO−2 + 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 HSO−3 → N(OH)(OSO−2)2 + H2O → NH(OH)(OSO−2) + HSO−4
NH(OH)(OSO−2) + [H3O]+ → [NH3OH]+ + HSO−4 (100 °C, 1 h)

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

A direct lab synthesis of hydroxylamine from molecular nitrogen in water plasma was demonstrated in 2024. [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

Hydroxylamine derivatives substituted in place of the hydroxyl or amine hydrogen are (respectively) called O- or N‑hydroxyl­amines. 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 and 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] and 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 Hoechst–Celanese 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

Hydroxylamine can be an explosive, with a theoretical decomposition energy of about 5 kJ/g, 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. Formally, amines are 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">Ammonium</span> Chemical compound

Ammonium is a modified form of ammonia that has an extra hydrogen atom. It is a positively charged (cationic) molecular ion with the chemical formula NH+4 or [NH4]+. It is formed by the addition of a proton to 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, 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">Zinc chloride</span> Chemical compound

Zinc chloride is an inorganic chemical compound with the formula ZnCl2·nH2O, with n ranging from 0 to 4.5, forming hydrates. Zinc chloride, anhydrous and its hydrates, are colorless or white crystalline solids, and are highly soluble in water. Five hydrates of zinc chloride are known, as well as four forms of anhydrous zinc chloride.

<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.

In chemistry, disproportionation, sometimes called dismutation, is a redox reaction in which one compound of intermediate oxidation state converts to two compounds, one of higher and one of lower oxidation state. The reverse of disproportionation, such as when a compound in an intermediate oxidation state is formed from precursors of lower and higher oxidation states, is called comproportionation, also known as symproportionation.

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

Sulfamic acid, also known as amidosulfonic acid, amidosulfuric acid, aminosulfonic acid, sulphamic acid and sulfamidic acid, is a molecular compound with the formula H3NSO3. This colourless, water-soluble compound finds many applications. Sulfamic acid melts at 205 °C before decomposing at higher temperatures to water, sulfur trioxide, sulfur dioxide and nitrogen.

<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.

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.

Hyponitrous acid is a chemical compound with formula H
2N
2O
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 or azanyl, 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.

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

Methoxyamine is the organic compound with the formula CH3ONH2. Also called O-methylhydroxylamine, it is a colourless volatile liquid that is soluble in polar organic solvent and in water. It is a derivative of hydroxylamine with the hydroxyl hydrogen replaced by a methyl group. Alternatively, it can be viewed as a derivative of methanol with the hydroxyl hydrogen replaced by an amino group. It is an isomer of N-methylhydroxylamine and aminomethanol. It decomposes in an exothermic reaction (-56 kJ/mol) to methane and azanone unless stored as a hydrochloride salt.

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.

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

Sulfoxylic acid (H2SO2) (also known as hyposulfurous acid or sulfur dihydroxide) is an unstable oxoacid of sulfur in an intermediate oxidation state between hydrogen sulfide and dithionous acid. It consists of two hydroxy groups attached to a sulfur atom. Sulfoxylic acid contains sulfur in an oxidation state of +2. Sulfur monoxide (SO) can be considered as a theoretical anhydride for sulfoxylic acid, but it is not actually known to react with water.

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

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  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

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