2,3-epoxypropyl-1,1-d2 4-nitrobenzoate | 128753-18-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2,3-epoxypropyl-1,1-d2 4-nitrobenzoate
• CAS: 128753-18-4
• 化学式: C₁₀H₉NO₅
• 分子量: 225.169
• InChiKey: MUWIANZPEBMVHH-NCYHJHSESA-N

反应信息

• 作为产物：
  描述：

  在 间氯过氧苯甲酸 作用下， 以 二氯甲烷 为溶剂， 反应 72.0h， 生成 2,3-epoxypropyl-1,1-d2 4-nitrobenzoate
  参考文献：
  名称：

  Methyleneoxirane-cyclopropanone and related rearrangements in C3H4O cation radicals and neutral molecules. A quest for the oxyallyl intermediate

  摘要：

  The formation, relative stabilities, isomerizations, and dissociations of several C3H4O cation radicals and neutral molecules have been investigated by neutralization-reionization mass spectrometry (NRMS) and ab initio calculations (MP4/6-31G*). The methyleneoxirane (1.+) and .CH2CH2CO+ (4.+) ions were found experimentally as stable, noninterconverting species, consistent with the results of ab initio calculations. Upon collisionally activated dissociation (CAD), prior to losing the ring methylene group, 1.+ undergoes partial degenerate isomerization via the oxyallyl ion, CH2-C(O.)CH2+ (3.+). The activation barriers for the 3.+ --> 1.+ and 1.+ --> 3.+ isomerizations were calculated as 8 and 105 kJ mol-1, respectively. The cyclopropanone cation radical 2.+, is unstable, representing a transition state for the degenerate isomerization of .CH2CH2CO+ (4.+), while the distonic ion CH2 = C+ - OCH2.(7.+) and the ion-molecule complex CH2 = CH2.+...OC (14.+) are stable. Neutral methyleneoxirane (1) is found to be a stable molecule that does not undergo extensive degenerate isomerization upon its formation from the ion 1.+. The biradical .CH2CH2CO. produced by neutralization of 4.+ is unstable, dissociating to C2H4 and CO in < 1-mu-s with a large kinetic energy release. NRMS is superior to CAD in distinguishing C3H4O.+ isomers.

  DOI：

  10.1021/ja00016a005