1-methyl-2-(4-hydroxystyryl)pyridiniumbetaine | 38039-62-2

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 1-methyl-2-(4-hydroxystyryl)pyridiniumbetaine
• 英文别名: 4-[(2E)-2-(1-methylpyridin-2-ylidene)ethylidene]cyclohexa-2,5-dien-1-one
• CAS: 38039-62-2
• 化学式: C₁₄H₁₃NO
• 分子量: 211.263
• InChiKey: WLHKMTNVCBYKQU-MDWZMJQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  16
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  20.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  2-(4-Hydroxystyryl)-1-methylpyridinium betaine 以 水 为溶剂， 生成 1-methyl-2-(4-hydroxystyryl)pyridiniumbetaine
  参考文献：
  名称：

  Effect of protonation on the molecular structure and reactivity of a typical merocyanine dye: experimental and theoretical investigation

  摘要：

  The molecular reactivity of 1-methyl-2-(4-hydroxystyryl)pyridiniumbetaine (M) is affected upon protonation in both ground and excited states. In aqueous solution, the protonated trans form is photochemically active and isomerizes to give the cis form. The quantum yields phi(tc) and phi(ct) are determined. The rate constant and the thermodynamic parameters of the reverse cis --> trans thermal reaction, from the unprotonated cis form, are also calculated. Due to the irreversibility of the thermal reaction, a complete molecular reaction cycle is performed in one direction. The excited molecule exhibits more acidic character than in the ground state. To correlate with the experimental work, ASED-MO calculations are applied for both unprotonated and protonated forms. The photochemical isomerization and the thermal reactions are discussed in terms of changes of the geometrical structure from the quinonoid to the benzenoid form upon protonation in both ground and excited states. Upon excitation, it seems that the molecular polarity character decreases in the case of M but increases for MH+. Protonation is found as an exothermic, downhitl reaction in the ground state and as an endothermic, uphill reaction in the excited state. It is shown that the lowest electronic transition is pi --> pi* which is higher for MH+ than for M.

  DOI：

  10.1021/j100115a017