双语化学辞典Chem Lexicon
概念 · 有机化学 · 反应中间体 Organic chemistry · Reactive intermediates

自由基Radical

高中High school
拼音 zì yóu jī 别名 free radical旧称 / 异名 游离基常见误译 根(radical 在旧式命名里也指“根”(如酸根),但作为单电子物种必须译作“自由基”) (radical once also meant a group such as an acid radical (根), but the species with an unpaired electron is 自由基)

定义Definition

自由基是含有未成对电子的原子、分子或离子,用一个圆点表示未成对电子,如 Cl•、CH₃•。它们通常由共价键均裂产生,大多数非常活泼。

A radical is an atom, molecule or ion with an unpaired electron, shown by a dot, as in Cl• and CH₃•. Radicals are usually formed by homolytic fission of a covalent bond, and most are highly reactive.

均裂与生成Homolytic fission

共价键断裂时,若成键电子对平均分给两个原子,每个原子各得一个电子,就生成两个自由基,这叫均裂。均裂需要能量,常由紫外光或加热提供,例如 Cl₂ 在紫外光下 Cl₂ → 2Cl•。弱键(如 O–O 键)较易均裂,过氧化物因此常用作自由基引发剂。

When a covalent bond breaks so that each atom keeps one of the bonding electrons, two radicals are formed; this is homolytic fission. It needs energy, usually supplied by ultraviolet light or heat, e.g. Cl₂ → 2Cl• in UV light. Weak bonds such as O–O break most easily, which is why peroxides are used as radical initiators.

自由基取代:链反应Free-radical substitution: a chain reaction

甲烷与氯气在紫外光下发生自由基取代,分三个阶段。引发:Cl₂ → 2Cl•。增长:CH₄ + Cl• → CH₃• + HCl,CH₃• + Cl₂ → CH₃Cl + Cl•,每一步都再生出一个自由基,使反应持续下去。终止:两个自由基结合,如 CH₃• + Cl• → CH₃Cl、2CH₃• → C₂H₆。生成的乙烷说明反应经过了甲基自由基。产物往往是多种取代物的混合物。

Methane and chlorine undergo free-radical substitution in UV light in three stages. Initiation: Cl₂ → 2Cl•. Propagation: CH₄ + Cl• → CH₃• + HCl, then CH₃• + Cl₂ → CH₃Cl + Cl•; each step regenerates a radical, so the chain continues. Termination: two radicals combine, e.g. CH₃• + Cl• → CH₃Cl or 2CH₃• → C₂H₆. The ethane formed is evidence for methyl radicals. The product is usually a mixture of substitution products.

大气与生命中的自由基Radicals in the atmosphere and in living things

氯氟烃在平流层受紫外光照射放出 Cl•,Cl• 催化臭氧分解:Cl• + O₃ → ClO• + O₂,ClO• + O → Cl• + O₂,一个氯原子可破坏大量臭氧分子。NO 和 NO₂ 也是自由基。在生物体内,活性氧自由基会损伤 DNA 和膜脂,维生素 E 等抗氧化剂可以捕获它们。

In the stratosphere, UV light releases Cl• from chlorofluorocarbons, and Cl• catalyses ozone breakdown: Cl• + O₃ → ClO• + O₂, then ClO• + O → Cl• + O₂, so one chlorine atom destroys many ozone molecules. NO and NO₂ are also radicals. In living organisms, reactive oxygen radicals damage DNA and membrane lipids; antioxidants such as vitamin E trap them.

年表Timeline

  • 1900

    冈伯格制得三苯甲基自由基,第一个被确认的有机自由基

    Gomberg prepares the triphenylmethyl radical, the first organic radical recognised

  • 1929

    帕内特用铅镜实验证明气相中存在甲基自由基

    Paneth's lead-mirror experiment shows methyl radicals exist in the gas phase

  • 1974

    莫利纳与罗兰指出氯氟烃释放的氯原子会破坏臭氧层

    Molina and Rowland show chlorine atoms from CFCs destroy stratospheric ozone

  • 1995

    克鲁岑、莫利纳、罗兰因臭氧层化学获诺贝尔化学奖

    Crutzen, Molina and Rowland receive the Nobel Prize in Chemistry for ozone-layer chemistry

相关公式Formulas

链反应与链长 Chain reactions and chain length→
\[\text{链长 } \nu = \frac{\text{链传递速率}}{\text{链引发速率}},\qquad \mathrm{H_2 + Br_2}:\ v = \frac{k[\mathrm H_2][\mathrm{Br_2}]^{1/2}}{1 + k'[\mathrm{HBr}]/[\mathrm{Br_2}]}\]\[\text{chain length} \nu = \frac{\text{propagation rate}}{\text{initiation rate}},\qquad \mathrm{H_2 + Br_2}:\ v = \frac{k[\mathrm H_2][\mathrm{Br_2}]^{1/2}}{1 + k'[\mathrm{HBr}]/[\mathrm{Br_2}]}\]