6-[(5-Bromo-2-hydroxyphenyl)methyl]-1,4,8,11-tetrazacyclotetradecane-5,7-dione | 188925-62-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 酚类
• 英文名称: 6-[(5-Bromo-2-hydroxyphenyl)methyl]-1,4,8,11-tetrazacyclotetradecane-5,7-dione
• CAS: 188925-62-4
• 化学式: C₁₇H₂₅BrN₄O₃
• 分子量: 413.314
• InChiKey: FWGFWRULNCNZGS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  103
• 氢给体数：
  5
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6-[(5-Bromo-2-hydroxyphenyl)methyl]-1,4,8,11-tetrazacyclotetradecane-5,7-dione 、 copper(II) nitrate 在 sodium hydroxide 作用下， 以 水 为溶剂， 生成
  参考文献：
  名称：

  Kinetics and mechanism of the acid dissociation of copper(II) complex of novel C-functionalized macrocylcic dioxotetramines

  摘要：

  The kinetics of the acid dissociation of copper(II) complex of a novel C-functionalized macrocyclic dioxotetraamine has been studied using a stopped-flow spectrophotometer. It was proven that substituents decrease the acid dissociation rates. The dissociation rate follows the law upsilon(d) = C(com)kK(1)K(2)H(2)/(1 + K1H + K1K2H2). On the intermediates we have obtained, the dissociation kinetics are interpreted by a mechanism involving the negatively charged carbonyl oxygen of the complex being rapidly protonated in a pre-equilibrium step, the rate-determining step being intramolecular hydrogen(enolic tautomer) migration(to imine nitrogen). The dissociation rate reached a plateau in strongly acidic solution. By means of temperatures coefficient method, K-1, K-2 of the pre-equilibrium step and Delta H-not equal and Delta S not equal of the rate-determining step were obtained and the results discussed. It is the strong in-plane ligand held that increased Delta H of the rate-determining step and thus decreases the dissociation rate constant. The Bronsted type linear free energy relationships do exist in this C-functionalized dioxotetraamine copper(II) complex. The results clarify insights into acid dissociation mechanisms for the 14-membered macrocyclic dioxotetraamine copper(II) complex. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0277-5387(96)00516-5
• 作为产物：
  描述：

  氢气 、 以 further solvent(s) 为溶剂， 生成 铜 、 6-[(5-Bromo-2-hydroxyphenyl)methyl]-1,4,8,11-tetrazacyclotetradecane-5,7-dione
  参考文献：
  名称：

  Kinetics and mechanism of the acid dissociation of copper(II) complex of novel C-functionalized macrocylcic dioxotetramines

  摘要：

  The kinetics of the acid dissociation of copper(II) complex of a novel C-functionalized macrocyclic dioxotetraamine has been studied using a stopped-flow spectrophotometer. It was proven that substituents decrease the acid dissociation rates. The dissociation rate follows the law upsilon(d) = C(com)kK(1)K(2)H(2)/(1 + K1H + K1K2H2). On the intermediates we have obtained, the dissociation kinetics are interpreted by a mechanism involving the negatively charged carbonyl oxygen of the complex being rapidly protonated in a pre-equilibrium step, the rate-determining step being intramolecular hydrogen(enolic tautomer) migration(to imine nitrogen). The dissociation rate reached a plateau in strongly acidic solution. By means of temperatures coefficient method, K-1, K-2 of the pre-equilibrium step and Delta H-not equal and Delta S not equal of the rate-determining step were obtained and the results discussed. It is the strong in-plane ligand held that increased Delta H of the rate-determining step and thus decreases the dissociation rate constant. The Bronsted type linear free energy relationships do exist in this C-functionalized dioxotetraamine copper(II) complex. The results clarify insights into acid dissociation mechanisms for the 14-membered macrocyclic dioxotetraamine copper(II) complex. (C) 1997 Published by Elsevier Science Ltd.

  DOI：

  10.1016/s0277-5387(96)00516-5