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Size-dependent rate acceleration in the silylation of secondary alcohols: the bigger the faster

机译：仲醇的甲硅烷基化中与尺寸有关的速率加速：越大越快

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Relative rates for the reaction of secondary alcohols carrying large aromatic moieties with silyl chlorides carrying equally large substituents have been determined in organic solvents. Introducing thoroughly matching pairs of big dispersion energy donor (DED) groups enhanced rate constants up to four times, notably depending on the hydrogen bond donor ability of the solvent. A linear correlation between computed dispersion energy contributions to the stability of the silyl ether products and experimental relative rate constants was found. These results indicate a cooperation between solvophobic effects and DED-groups in the kinetic control of silylation reactions.

机译：已经确定了在有机溶剂中带有大芳族部分的仲醇与带有同样大取代基的甲硅烷基氯反应的相对速率。引入完全匹配的大分散能量供体（DED）基对可将速率常数提高多达四倍，特别是取决于溶剂的氢键供体能力。发现计算的分散能对甲硅烷基醚产物的稳定性的贡献与实验相对速率常数之间存在线性关系。这些结果表明，在甲硅烷基化反应的动力学控制中，疏溶剂作用和DED-基团之间存在协同作用。

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期刊名称 Chemical Science
作者
Marta Marin-Luna; Benjamin Pölloth; Fabian Zott; Hendrik Zipse;
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年(卷),期 2018(9),31
年度 2018
页码 6509–6515
总页数 7
原文格式 PDF
正文语种
中图分类生化遗传学;生化药理学;
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专利

1. Size-dependent rate acceleration in the silylation of secondary alcohols: the bigger the faster [J] . Marta Marin-Luna, Benjamin P?lloth, Fabian Zott, Chemical science . 2018,第31期

机译：仲醇的甲硅烷基化中与尺寸有关的速率加速：越大越快
2. Scientific Opinion on Flavouring Group Evaluation 63, Revision 3 (FGE.63Rev3): aliphatic secondary alcohols, ketones and related esters evaluated by JECFA (59th and 69th meetings) structurally related to saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched‐chain carboxylic acids evaluated by EFSA in FGE.07Rev4 [J] . Vittorio Silano, Claudia Bolognesi, Laurence Castle, EFSA Journal . 2017,第1期

机译：关于调味组评估63的科学意见，修订版3（FGE.63Rev3）：JECFA（第五十九次和第六十九次会议）评估的脂肪族仲醇，酮和相关酯的结构与饱和和不饱和脂肪族仲醇，酮和仲醇的酯有关由EFSA在FGE.07Rev4中评估的饱和直链或支链羧酸
3. Scientific Opinion on Flavouring Group Evaluation 63, Revision 2 (FGE.63Rev2): Consideration of aliphatic secondary alcohols, ketones and related esters evaluated by JECFA (59th and 69th meetings) structurally related to saturated and unsaturated aliphatic secondary alcohols, ketones and esters of secondary alcohols and saturated linear or branched‐chain carboxylic acids evaluated by EFSA in FGE.07Rev4 [J] . EFSA Journal . 2013,第4期

机译：关于调味剂组评估63的科学意见，修订版2（FGE.63Rev2）：考虑JECFA（第五十九和第六十九次会议）评估的与饱和和不饱和脂肪族仲醇，酮和仲酸酯结构相关的脂肪族仲醇，酮和相关酯EFSA在FGE.07Rev4中评估的醇和饱和的直链或支链羧酸
4. On the advantages of approximate vs. complete verification: bigger models, faster, less memory, usually accurate [C] . Owen, D., Menzies, . 2004

机译：具有近似验证和完整验证的优点：更大的模型，更快的内存，更少的存储空间，通常是准确的
5. A silylation based kinetic resolution of secondary alcohols and the synthesis and structural characterization of pyridyl-oxazolidine compounds [D] . Sheppard, Cody 2013

机译：基于甲硅烷基化的仲醇动力学拆分以及吡啶基-恶唑烷化合物的合成与结构表征
6. Scientific Opinion on Flavouring Group Evaluation 63 Revision 3 (FGE.63Rev3): aliphatic secondary alcohols ketones and related esters evaluated by JECFA (59th and 69th meetings) structurally related to saturated and unsaturated aliphatic secondary alcohols ketones and esters of secondary alcohols and saturated linear or branched‐chain carboxylic acids evaluated by EFSA in FGE.07Rev4 [O] . EFSA Panel on Food Contact Materials, Enzymes, Flavourings and Processing Aids (CEF), 2017

机译：关于调味组评估63的科学意见修订版3（FGE.63Rev3）：JECFA（第五十九次和第六十九次会议）评估的脂肪族仲醇酮和相关酯的结构与饱和和不饱和脂肪族仲醇酮和仲醇的酯有关由EFSA在FGE.07Rev4中评估的饱和直链或支链羧酸
7. Amines vs. N-Oxides as Organocatalysts for Acylation, Sulfonylation and Silylation of Alcohols: 1-Methylimidazole N-Oxide as an Efficient Catalyst for Silylation of Tertiary Alcohols [O] . Murray JI, Spivey AC 2015

机译：胺与N-氧化物作为有机催化剂用于醇的酰化，磺酰化和甲硅烷基化：1-甲基咪唑N-氧化物作为叔醇的甲硅烷基化的有效催化剂

Size-dependent rate acceleration in the silylation of secondary alcohols: the bigger the faster

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