Difference between revisions of "Hypofluorous acid"
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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, 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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| + | A solution of hypofluorous acid in [[acetonitrile]] is significanly more stable that the pure compound, due to the formation of a [[Hydrogen bond|hydrogen-bonded]] [[adduct]], MeCN·HOF.<ref>{{citation | first1 = Shlomo | last1 = Rozen | first2 = Yifat | last2 = Bareket | first3 = Moshe | last3 = Kol | title = HOF·CH<sub>3</sub>CN, made directly from F<sub>2</sub> and water, as an ecologically friendly oxidizing reagent | journal = Tetrahedron | volume = 49 | issue = 36 | year = 1993 | pages = 8169–78 | doi = 10.1016/S0040-4020(01)88036-4}}.</ref><ref>{{citation | first1 = Evan H. | last1 = Appelman | first2 = Oliver | last2 = Dunkelberg | first3 = Moshe | last3 = Kol | title = Hypofluorous acid and acetonitrile: the taming of a reagent | journal = J. Fluorine Chem. | volume = 56 | issue = 2 | year = 1992 | pages = 199–213 | doi = 10.1016/S0022-1139(00)81103-3}}.</ref> 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== | ==Preparation== | ||
Revision as of 11:31, 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 | [] |
| ChemSpider | |
| 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 ΔfH |
−98.32 kJ mol−1 |
| Standard molar entropy S |
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) | |
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
- ↑ For example, hypochlorous acid, HOCl.
References
- ↑ Greenwood, Norman N.; Earnshaw, A. Chemistry of the Elements; Pergamon: Oxford, 1984; p 1003. ISBN 0-08-022057-6.
- ↑ 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.
- ↑ 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).
- ↑ 4.0 4.1 Studier, Martin H.; Appleman, Evan H. Hypofluorous Acid. J. Am. Chem. Soc. 1971, 93 (9), 2349–51. DOI: 10.1021/ja00738a059.
- ↑ 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.
- ↑ 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.
- ↑ Dennis, L. M.; Rochow, E. G. Oxyacids of Fluorine. J. Am. Chem. Soc. 1932, 54 (2), 832–33. DOI: 10.1021/ja01341a518.
- ↑ Dennis, L. M.; Rochow, E. G. Oxyacids of Fluorine. II. J. Am. Chem. Soc. 1933, 55 (6), 2431–34. DOI: 10.1021/ja01333a033.
- ↑ 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.
External links
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See also the corresponding article on Wikipedia. |
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