Dipartimento di Chimica "Giacomo Ciamician", Università di Bologna, Via F. Selmi 2, 40126 Bologna, Italy.
Scuola Superiore Meridionale, Università di Napoli Federico II, Largo San Marcellino 10, 80138 Naples, Italy.
Chem Commun (Camb). 2022 Feb 22;58(16):2750-2753. doi: 10.1039/d1cc06919e.
Prebiotic sugars are thought to be formed on primitive Earth by the formose reaction. However, their formation is not fully understood and it is plausible that key intermediates could have formed in extraterrestrial environments and subsequently delivered on early Earth by cometary bodies. 1,2-Ethenediol, the enol form of glycolaldehyde, represents a highly reactive intermediate of the formose reaction and is likely detectable in the interstellar medium. Here, we report the identification and first characterization of ()-1,2-ethenediol by means of rotational spectroscopy. The title compound has been produced in the gas phase by flash vacuum pyrolysis of bis--5-norbornene-2,3-diol at 750 °C, through a retro-Diels-Alder reaction. The spectral analysis was guided by high-level quantum-chemical calculations, which predicted spectroscopic parameters in very good agreement with the experiment. Our study provides accurate spectral data to be used for searches of ()-1,2-ethenediol in the interstellar space.
被认为是由原始地球上的福莫尔反应形成的。然而，它们的形成并不完全清楚，很可能关键中间体可以在天体环境中形成，并随后通过彗星体输送到早期地球。1,2-乙二烯醇，甘油醛的烯醇形式，代表福莫尔反应的高反应性中间体，并且很可能在星际介质中可检测到。在这里，我们通过旋转光谱法报告了（）-1,2-乙二烯醇的鉴定和首次表征。标题化合物通过在 750°C 下闪蒸真空热解双（-5-降冰片烯-2,3-二醇）以反-Diels-Alder 反应在气相中产生。光谱分析由高精度量子化学计算指导，该计算非常好地预测了与实验相符的光谱参数。我们的研究提供了准确的光谱数据，可用于在星际空间中搜索（）-1,2-乙二烯醇。
