Difference between revisions of "Hypofluorous acid"

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| Name = Rozen's reagent
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| IUPACName = acetonitrile—fluoranol (1/1)
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|  InChI=1/C2H3N.FHO/c1-2-3;1-2/h1H3;2H
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|  StdInChI=1S/C2H3N.FHO/c1-2-3;1-2/h1H3;2H
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|  InChIKey = MHXSJBXDLWNIAN-UHFFFAOYAK
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'''Hypofluorous acid''', HOF, is an unstable compound arising from the reaction of gaseous [[fluorine]] with water. It was first isolated in weighable quantities in 1971.<ref name="1stPrep">{{citation | last1 = Studier | first1 = Martin H. | last2 = Appleman | first2 =  Evan H. | title = Hypofluorous Acid | journal = J. Am. Chem. Soc. | year = 1971 | volume = 93 | issue = 9 | pages = 2349–51 | doi = 10.1021/ja00738a059}}.</ref> Despite the name, formed by analogy with other halogen compounds of similar formula,<ref group="Note">For example, [[hypochlorous acid]], HOCl.</ref> HOF is not significantly acidic, and hypofluorite salts are unknown.
 
'''Hypofluorous acid''', HOF, is an unstable compound arising from the reaction of gaseous [[fluorine]] with water. It was first isolated in weighable quantities in 1971.<ref name="1stPrep">{{citation | last1 = Studier | first1 = Martin H. | last2 = Appleman | first2 =  Evan H. | title = Hypofluorous Acid | journal = J. Am. Chem. Soc. | year = 1971 | volume = 93 | issue = 9 | pages = 2349–51 | doi = 10.1021/ja00738a059}}.</ref> Despite the name, formed by analogy with other halogen compounds of similar formula,<ref group="Note">For example, [[hypochlorous acid]], HOCl.</ref> HOF is not significantly acidic, and hypofluorite salts are unknown.
  
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===References===
 
===References===
 
{{reflist}}
 
{{reflist}}
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===Further reading===
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*{{citation | title = The Crystal Structure of Hypofluorous Acid: Chain Formation by OH…O Hydrogen Bonds |
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first1 = Wolfgang | last1 = Poll | first2 = Gottfried | last2 = Pawelke | first3 = Dietrich | last3 = Mootz | first4 = Evan H. | last4 = Appelman | Angew. Chem. Int. Ed. Engl. | volume = 27 | issue = 3 | pages = 392–93 | year = 1988 | doi = 10.1002/anie.198803921}}.
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*{{citation | first1 = Moshe | last1 = Kol | first2 = Shlomo | last2 = Rozen | title = Functionalization of aromatic molecules using HOF·CH<sub>3</sub>CN and CH<sub>3</sub>OF | journal = J. Org. Chem. | year = 1993 | volume = 58 | issue = 6 | pages = 1593–95 | doi = 10.1021/jo00058a052}}.
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*{{citation | first1 = Shlomo | last1 = Rozen | first2 = Michael | last2 = Brand | first3 = Moshe | last3 = Kol | title = Tertiary hydroxylation using fluorine: activation of the carbon–hydrogen bond | journal = J. Am. Chem. Soc. | year = 1989 | volume = 111 | issue = 21 | pages = 8325–26 | doi = 10.1021/ja00203a069}}.
  
 
==External links==
 
==External links==

Revision as of 12:25, 17 September 2010

Hypofluorous acid
IUPAC name fluoranol
Other names oxygen fluoride hydride
Identifiers
InChI InChI=1/FHO/c1-2/h2H
InChIKey AQYSYJUIMQTRMV-UHFFFAOYAN
Standard InChI InChI=1S/FHO/c1-2/h2H
Standard InChIKey AQYSYJUIMQTRMV-UHFFFAOYSA-N
CAS number [14034-79-8]
ChemSpider 109936
Properties[1]
Chemical formula HOF
Molar mass 36.006 g mol−1
Appearance see text
Melting point

−117 °C

Boiling point

< 0 °C

Solubility in water reacts
Structure[2]
Molecular geometry bent: H–O = 96.4(10) pm, O–F = 144.2(1) pm, H–O–F = 97.2(6)°
Thermochemistry[3]
Std enthalpy of formation ΔfHo298 −98.32 kJ mol−1
Standard molar entropy So298 226.77 J K−1 mol−1
Related compounds
Other compounds Hypochlorous acid
Hypobromous acid
Hypoiodous acid
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Rozen's reagent
IUPAC name acetonitrile—fluoranol (1/1)
Identifiers
InChI InChI=1/C2H3N.FHO/c1-2-3;1-2/h1H3;2H
InChIKey MHXSJBXDLWNIAN-UHFFFAOYAK
Standard InChI InChI=1S/C2H3N.FHO/c1-2-3;1-2/h1H3;2H
Standard InChIKey MHXSJBXDLWNIAN-UHFFFAOYSA-N
ChemSpider 9226732
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Hypofluorous acid, HOF, is an unstable compound arising from the reaction of gaseous fluorine with water. It was first isolated in weighable quantities in 1971.[4] Despite the name, formed by analogy with other halogen compounds of similar formula,[Note 1] HOF is not significantly acidic, and hypofluorite salts are unknown.

A solution of hypofluorous acid in acetonitrile is significanly more stable that the pure compound, due to the formation of a hydrogen-bonded adduct, MeCN·HOF.[5][6] This species is sometimes called Rozen's reagent, and is a strong oxidizing agent through oxygen transfer: it is particularly useful for epoxidation reactions.

Preparation

Reported preparations of hypofluorous acid in the 1930s[7][8] are now considered erroneous.[4] The first clear observation of HOF was through the infrared spectrum of a matrix isolation sample, obtained by photolysis of a mixture of fluorine and water in a nitrogen matrix at 14–20 K.[9]

Notes and references

Notes

  1. ↑ For example, hypochlorous acid, HOCl.

References

  1. ↑ Greenwood, Norman N.; Earnshaw, A. Chemistry of the Elements; Pergamon: Oxford, 1984; p 1003. ISBN 0-08-022057-6.
  2. ↑ Kim, Hyunyong; Pearson, Edwin F.; Appelman, Evan H. Millimeter‐Wave Spectrum and Structure of Hypofluorous Acid: HOF and DOF. J. Chem. Phys. 1972, 56 (1), 1–3. DOI: 10.1063/1.1676830.
  3. ↑ Hypofluorous acid. In NIST Chemistry WebBook; National Institute for Standards and Technology, <http://webbook.nist.gov/cgi/inchi/InChI%3DInChI=1S/FHO/c1-2/h2H>. (accessed 17 September 2010).
  4. ↑ 4.0 4.1 Studier, Martin H.; Appleman, Evan H. Hypofluorous Acid. J. Am. Chem. Soc. 1971, 93 (9), 2349–51. DOI: 10.1021/ja00738a059.
  5. ↑ Rozen, Shlomo; Bareket, Yifat; Kol, Moshe HOF·CH3CN, made directly from F2 and water, as an ecologically friendly oxidizing reagent. Tetrahedron 1993, 49 (36), 8169–78. DOI: 10.1016/S0040-4020(01)88036-4.
  6. ↑ Appelman, Evan H.; Dunkelberg, Oliver; Kol, Moshe Hypofluorous acid and acetonitrile: the taming of a reagent. J. Fluorine Chem. 1992, 56 (2), 199–213. DOI: 10.1016/S0022-1139(00)81103-3.
  7. ↑ Dennis, L. M.; Rochow, E. G. Oxyacids of Fluorine. J. Am. Chem. Soc. 1932, 54 (2), 832–33. DOI: 10.1021/ja01341a518.
  8. ↑ Dennis, L. M.; Rochow, E. G. Oxyacids of Fluorine. II. J. Am. Chem. Soc. 1933, 55 (6), 2431–34. DOI: 10.1021/ja01333a033.
  9. ↑ Noble, Paul N.; Pimentel, George C. Hypofluorous acid: Infrared spectrum and vibrational potential function. Spectrochim. Acta Part A 1968, 24 (7), 797–806. DOI: 10.1016/0584-8539(68)80177-1.

Further reading

External links

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