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,<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. | ||
| − | 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. | + | 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 | title = Epoxidation of Olefins with Elemental Fluorine in Water/Acetonitrile Mixtures | first1 = Shlomo | last1 = Rozen | first2 = Michael | last2 = Brand | journal = Angew. Chem. Int. Ed. Engl | volume = 25 | issue = 6 | pages = 554–55 | year = 1986 | doi = 10.1002/anie.198605541}}.</ref><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== | ||
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===Further reading=== | ===Further reading=== | ||
*{{citation | title = The Crystal Structure of Hypofluorous Acid: Chain Formation by OH…O Hydrogen Bonds | | *{{citation | title = The Crystal Structure of Hypofluorous Acid: Chain Formation by OH…O Hydrogen Bonds | | ||
| − | 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}}. | + | first1 = Wolfgang | last1 = Poll | first2 = Gottfried | last2 = Pawelke | first3 = Dietrich | last3 = Mootz | first4 = Evan H. | last4 = Appelman | journal = Angew. Chem. Int. Ed. Engl. | volume = 27 | issue = 3 | pages = 392–93 | year = 1988 | doi = 10.1002/anie.198803921}}. |
*{{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}}. | *{{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}}. | ||
*{{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}}. | *{{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}}. | ||
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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.[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][7] This species is sometimes called Rozen's reagent, and is a strong oxidizing agent through oxygen transfer: it is particularly useful for epoxidation reactions.
Contents
Preparation
Reported preparations of hypofluorous acid in the 1930s[8][9] 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.[10]
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; Brand, Michael Epoxidation of Olefins with Elemental Fluorine in Water/Acetonitrile Mixtures. Angew. Chem. Int. Ed. Engl 1986, 25 (6), 554–55. DOI: 10.1002/anie.198605541.
- ↑ 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.
Further reading
- Poll, Wolfgang; Pawelke, Gottfried; Mootz, Dietrich; Appelman, Evan H. The Crystal Structure of Hypofluorous Acid: Chain Formation by OH…O Hydrogen Bonds. Angew. Chem. Int. Ed. Engl. 1988, 27 (3), 392–93. DOI: 10.1002/anie.198803921.
- Kol, Moshe; Rozen, Shlomo Functionalization of aromatic molecules using HOF·CH3CN and CH3OF. J. Org. Chem. 1993, 58 (6), 1593–95. DOI: 10.1021/jo00058a052.
- Rozen, Shlomo; Brand, Michael; Kol, Moshe Tertiary hydroxylation using fluorine: activation of the carbon–hydrogen bond. J. Am. Chem. Soc. 1989, 111 (21), 8325–26. DOI: 10.1021/ja00203a069.
External links
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See also the corresponding article on Wikipedia. |
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