Bottom-Up Synthesis of 1,1-Ethenediol (H2CC(OH)2)─The Simplest Unsaturated Geminal Diol─In Interstellar Analogue Ices,The Journal of Physical Chemistry Letters

当前位置： X-MOL 学术 › J. Phys. Chem. Lett. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Bottom-Up Synthesis of 1,1-Ethenediol (H2CC(OH)2)─The Simplest Unsaturated Geminal Diol─In Interstellar Analogue Ices
The Journal of Physical Chemistry Letters ( IF 4.8 ) Pub Date : 2021-12-30 , DOI: 10.1021/acs.jpclett.1c03515
N Fabian Kleimeier _{1,

2} , Ralf I Kaiser _{1,

2}

Affiliation

Because of their nucleophilic character and high reactivity, enols─reaction intermediates carrying a hydroxyl group connected to a carbon–carbon double bond─play a key role in the formation of complex organic molecules in astrobiology and biochemistry. Here, we report the first bottom-up preparation of 1,1-ethenediol (H₂CC(OH)₂)─the simplest unsaturated geminal enol of acetic acid (CH₃COOH) and potential precursor for the formation of glycine─in interstellar analogue ices of carbon dioxide and methane processed by proxies of galactic cosmic rays. These enols can easily form via nonequilibrium chemistry in low temperature (10 K) interstellar ices at abundances orders of magnitude higher than thermodynamically predicted. These energetically less favorable tautomers remain stable in ice-coated interstellar nanoparticles in molecular clouds and also upon sublimation into the gas phase in star forming regions thus providing the raw material to a complex and exotic organic chemistry under extreme conditions in deep space.

中文翻译：

自下而上合成 1,1-乙烯二醇 (H2CC(OH)2)─最简单的不饱和双二醇─在星际模拟冰中

由于其亲核特性和高反应性，烯醇——带有与碳-碳双键相连的羟基的反应中间体——在天体生物学和生物化学中复杂有机分子的形成中起着关键作用。在这里，我们报告了第一个自下而上制备 1,1-乙二醇 (H ₂ CC(OH) ₂ )——最简单的乙酸不饱和偕烯醇 (CH ₃COOH）和甘氨酸形成的潜在前体——在由银河宇宙射线的代理处理的二氧化碳和甲烷的星际模拟冰中。这些烯醇可以很容易地通过低温（10 K）星际冰中的非平衡化学形成，其丰度比热力学预测的高几个数量级。这些能量上不太有利的互变异构体在分子云中冰覆盖的星际纳米粒子中以及在恒星形成区域升华成气相时保持稳定，从而为深空极端条件下的复杂和奇异的有机化学提供原材料。

更新日期：2022-01-13

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南