methyl nitrate conjugate monoacid | 99573-80-5

• 分子结构分类: 有机化合物 - 有机1,3-偶极化合物 - 烯丙基型1,3-偶极有机化合物
• 英文名称: methyl nitrate conjugate monoacid
• CAS: 99573-80-5
• 化学式: CH₄NO₃
• 分子量: 78.0477
• InChiKey: LRMHVVPPGGOAJQ-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  -0.66
• 重原子数：
  5.0
• 可旋转键数：
  1.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  55.94
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  methyl nitrate conjugate monoacid 在 水 作用下， 生成 甲醇
  参考文献：
  名称：

  Is the Proton Affinity of Nitric Acid Larger Than the Proton Affinity of Methyl Nitrate? A Direct Experimental Answer

  摘要：

  A direct experimental approach based on the evaluation of the ligand exchange equilibrium H2O-NO2+ + CH3OH reversible arrow CH3(H)O-NO2+ + H2O has been exploited for the determination of Delta PA = PA(HNO3) - PA(CH3ONO2) at 298 K. The result, Delta PA = 4.0 +/- 1.2 kcal mol(-1), is sufficiently accurate to provide firm experimental support to the counterintuitive prediction, based on high-level ab initio calculations, that the PA of HNO3 exceeds that of CH3ONO2 by 5.6 +/- 5 kcal mol(-1). Combination of the experimental Delta PA with the known PA of CH(3)ONO2 gives PA(HNO3) = 182.0 +/- 2.3 kcal mol(-1), in excellent agreement with the theoretically computed value, 182.5 +/- 3 kcal mol(-1). An explanation of the considerably lower PA(HNO3) value derived from earlier ICR bracketing experiments is offered, based on the R(H)O-NO2+ vs RONO(2)H(+) isomerism, whose role in determining the observed PA trend along the RONO(2) series (R = H, CH3, C2H5) is discussed.

  DOI：

  10.1021/ja00093a048