Gas-phase detection of oxirene

被引:7
作者
Wang, Jia [1 ,2 ]
Marks, Joshua H. [1 ,2 ]
Turner, Andrew M. [1 ,2 ]
Mebel, Alexander M. [3 ]
Eckhardt, Andre K. [4 ]
Kaiser, Ralf I. [1 ,2 ]
机构
[1] Univ Hawaii Manoa, W M Keck Res Lab Astrochem, Honolulu, HI 96822 USA
[2] Univ Hawaii Manoa, Dept Chem, Honolulu, HI 96822 USA
[3] Florida Int Univ, Dept Chem & Biochem, Miami, FL 33199 USA
[4] Ruhr Univ Bochum, Lehrstuhl Organische2, D-44801 Bochum, Germany
基金
美国国家科学基金会;
关键词
AB-INITIO; WOLFF REARRANGEMENT; BASIS-SETS; KETENE; DECOMPOSITION; PHOTOLYSIS; MOLECULES; CHEMISTRY; MECHANISM; ISOMERS;
D O I
10.1126/sciadv.adg1134
中图分类号
O [数理科学和化学]; P [天文学、地球科学]; Q [生物科学]; N [自然科学总论];
学科分类号
07 ; 0710 ; 09 ;
摘要
Oxirenes-highly strained 4p Huckel antiaromatic organics-have been recognized as key reactive intermediates in the Wolff rearrangement and in interstellar environments. Predicting short lifetimes and tendency toward ring opening, oxirenes are one of the most mysterious classes of organic transients, with the isolation of oxirene (c-C2H2O) having remained elusive. Here, we report on the preparation of oxirene in low-temperature methanol-acetaldehyde matrices upon energetic processing through isomerization of ketene (H2CCO) followed by resonant energy transfer of the internal energy of oxirene to the vibrational modes (hydroxyl stretching and bending, methyl deformation) of methanol. Oxirene was detected upon sublimation in the gas phase exploiting soft photoionization coupled with a reflectron time-of-flight mass spectrometry. These findings advance our fundamental understanding of the chemical bonding and stability of cyclic, strained molecules and afford a versatile strategy for the synthesis of highly ring-strained transients in extreme environments.
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页数:1
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