オキソニウムイオン
WordNet
- a particle that is electrically charged (positive or negative); an atom or molecule or group that has lost or gained one or more electrons
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- イオン
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出典(authority):フリー百科事典『ウィキペディア(Wikipedia)』「2015/11/25 01:14:21」(JST)
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In chemistry, an oxonium ion is any oxygen cation with three bonds. [1] The simplest oxonium ion is the hydronium ion H3O+. Another class of oxonium ions frequently encountered in organic chemistry is the oxocarbenium ions, obtained by protonation or alkylation of a carbonyl group e.g. R-C=O+-R' which forms a resonance structure with the fully fledged carbocation R-C+-O-R' and is therefore especially stable:
-
Stable alkyloxonium salts exist; they are extensively used as alkylating agents. For example, triethyloxonium tetrafluoroborate (Et
3O+
)(BF−
4) is a white crystalline solid. It is a powerful ethylating agent. It can be used, for example, to produce ethyl esters when the conditions of traditional Fischer esterification are unsuitable.[2] It is also used for preparation of enol ethers and related functional groups.[3][4]
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general pyramidal
oxonium ion
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skeletal formula of the
trimethyloxonium cation
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ball-and-stick model
of trimethyloxonium
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space-filling model
of trimethyloxonium
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Other hydrocarbon oxonium ions are formed by protonation or alkylation of alcohols or ethers (R-C-O+
-R
1R
2). In acidic media, the oxonium functional group produced by protonating an alcohol can be a leaving group in the E2 elimination reaction, because when it receives an electron, it becomes a water molecule. The product is an alkene. Extreme acidity, heat and dehydrating conditions are usually required.
Oxatriquinane and oxatriquinacene are unusually stable oxonium ions, first described in 2008. Oxatriquinane does not react with boiling water or with alcohols, thiols, halide ions, or amines, although it does react with stronger nucleophiles such as hydroxide, cyanide, and azide.
See also
- Onium compounds
- Pyrylium salt
References
- ^ March, Jerry (1985), Advanced Organic Chemistry: Reactions, Mechanisms, and Structure (3rd ed.), New York: Wiley, ISBN 0-471-85472-7
- ^ Douglas J. Raber, Patrick Gariano, Jr, Albert O. Brod, Anne L. Gariano, And Wayne C. Guida "Esterification Of Carboxylic Acids With Trialkyloxonium Salts: Ethyl And Methyl 4-acetoxybenzoates" Org. Synth. 1977, volume 56, 59.doi:10.15227/orgsyn.056.0059
- ^ Justin R. Struble And Jeffrey W. Bode "Synthesis Of A N-mesityl Substituted Aminoindanol-derived Triazolium Salt" Org. Synth. 2010, volume 87, 362. doi:10.15227/orgsyn.087.0362
- ^ Lous S. Hegedus, Michael A. Mcguire, And Lisa M. Schultze "1,3-Dimethyl-3-methoxy-4-phenylazetidinone" Org. Synth. 1987, volume 65, 140.doi:10.15227/orgsyn.065.0140
UpToDate Contents
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English Journal
- Gold(III) Chloride Catalyzed Synthesis of Chiral Substituted 3-Formyl Furans from Carbohydrates: Application in the Synthesis of 1,5-Dicarbonyl Derivatives and Furo[3,2-c]pyridine.
- Mal K1, Sharma A, Das I.
- Chemistry (Weinheim an der Bergstrasse, Germany).Chemistry.2014 Sep 8;20(37):11932-45. doi: 10.1002/chem.201402286. Epub 2014 Jul 30.
- This report describes a gold(III)-catalyzed efficient general route to densely substituted chiral 3-formyl furans under extremely mild conditions from suitably protected 5-(1-alkynyl)-2,3-dihydropyran-4-one using H2 O as a nucleophile. The reaction proceeds through the initial formation of an activa
- PMID 25077819
- C-H functionalization of sp3 centers with aluminum: a computational and mechanistic study of the Baddeley reaction of decalin.
- Lyall CL, Sato M, Uosis-Martin M, Asghar SF, Jones MD, Williams IH, Lewis SE.
- Journal of the American Chemical Society.J Am Chem Soc.2014 Sep 8. [Epub ahead of print]
- Decalin undergoes reaction with aluminum trichloride and acetyl chloride to form a tricyclic enol ether in good yield, as first reported by Baddeley. This eye-catching transformation, which may be considered to be an aliphatic Friedel-Crafts reaction, has not previously been studied mechanistically.
- PMID 25196493
- Synthesis of Polyketide Stereoarrays Enabled by a Traceless Oxonia-Cope Rearrangement.
- Yang L1, He G, Yin R, Zhu L, Wang X, Hong R.
- Angewandte Chemie (International ed. in English).Angew Chem Int Ed Engl.2014 Sep 4. doi: 10.1002/anie.201407231. [Epub ahead of print]
- Polyketide antibiotics bearing skipped polyols represent a synthetic challenge. A SiCl4 -promoted oxonia-Cope rearrangement of syn,syn-2-vinyl-1,3-diols was developed to forge an array of 1,5-pentenediols, thus providing versatile motifs for the preparation of 1,2,3,5-stereoarrays in a highly stereo
- PMID 25196242
Japanese Journal
- S053011 PEFC触媒層のionomer内における酸素拡散に関する分子論的研究([S05301]次世代電池のナノ・マイクロフルイディクス(1))
- 坂井 公則,徳増 崇
- 年次大会 : Mechanical Engineering Congress, Japan 2011, "S053011-1"-"S053011-4", 2011-09-11
- … In this research, we constructed the system including PFSA membrane, water, oxonium ion and platinum layers by using molecular dynamics study and researched about the effect of the water content of the ionomer on the structure of the ionomer and the permeability of the oxygen molecule. …
- NAID 110009759889
- 0303 PEFCカソード側触媒層イオノマー内の酸素拡散に関する研究(OS3-1 ナノスケールの熱流動現象,オーガナイズドセッション)
- 坂井 公則,徳増 崇
- 流体工学部門講演会講演論文集 2010, 103-104, 2010-10-29
- … We made the system including nafion, water, oxonium ion, nanoparticle platinum on a carbon layer by using molecular dynamics study, and researched about the structure of ionomer and the permeability of the oxygen molecule. …
- NAID 110008739456
- 飽和に近い条件におけるガラス固化体の溶解メカニズムに関する研究の現状と今後の課題
- 前田 敏克,山口 徹治,馬場 恒孝 [他],臼井 秀雄
- 日本原子力学会和文論文誌 = Transactions of the Atomic Energy Society of Japan 9(3), 233-242, 2010-09-01
- … Based on an extended literature survey covering recent studies on high-level radioactive glass dissolution under nearly saturated conditions, we have reached the conclusion that the slow dissolution is controlled by the diffusion of oxonium or boron ions in an altered layer formed on the glass surface. …
- NAID 10026648175
Related Links
- Oxonium-ion definition, hydronium ion. See more. Thesaurus Translate Reference Word of the Day Blog Slideshows Apps by Dictionary My Account Log Out Log In follow Dictionary.com Dictionary Thesaurus Translate More...
- オキソニウムイオン【oxonium ion】とは。意味や解説、類語。水和した水素イオンH3O+のこと。かつてヒドロニウムイオンとよばれた。 - goo国語辞書は27万語以上を収録。政治・経済・医学・ITなど、最新用語の追加も定期的に行って ...
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特発性大腿骨頭壊死症