2-naphthylammonium ion | 70902-53-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 2-naphthylammonium ion
• 英文别名: naphthalen-2-ylamine; protonated form；2-ammonio-naphthalene；2-Naphthylammonium；Naphthalen-2-aminium；naphthalen-2-ylazanium
• CAS: 70902-53-3
• 化学式: C₁₀H₉N*H
• 分子量: 144.196
• InChiKey: JBIJLHTVPXGSAM-UHFFFAOYSA-O

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  27.6
• 氢给体数：
  1
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  二苯甲酮 、 2-naphthylammonium ion 以 硫酸 为溶剂， 生成 羟基-二苯基-甲基 、 2-萘胺
  参考文献：
  名称：

  激光闪光光解法研究三重态2-萘基铵离子向二苯甲酮的氢原子转移反应：显着的质子效应

  摘要：

  The laser flash photolysis study at 355 nm in the 2-naphthylammonium ion (RNH3+) and benzophenone (BP) system has been carried out in methanol-water (9:1 v/v) at 290 K. At first, triplet benzophenone (3BP*) produced by fast intersystem crossing of 1BP* excited at 355 nm is quenched by RNH3+ with almost diffusion-controlled rates (1.1 x 10(10) M-1 s-1 at [H2SO4] = 0.015 M; 3.9 x 10(9) M-1 s-1 at [H2SO4] = 0.5 M). The triplet 2-naphthylammonium ion (3RNH3+*) is produced in the nanosecond region by triplet energy transfer from 3BP* to RNH3+ with efficiencies of 0.41 ([H2SO4] = 0.015 M) and 0.33 ([H2SO4] = 0.5 M) at [RNH3+] = 3.0 x 10(-3) M and at [BP] = 1.12 x 10(-2) M, competing with hydrogen abstraction of 3BP* from solvent (methanol) or RNH3+ molecules. Subsequently, in the microsecond region the hydrogen atom transfer (HT) reaction from 3RNH3+* to ground BP occurs effectively to give the naphthylamine cation radical (RNH2.+) and the ketyl radical (> COH). The decay rate (tau-obsd)-1 of 3RNH3+* increases with an increase of the BP concentration, and at higher BP concentrations a leveling off is observed. The (tau-obsd)-1 value decreases drastically with an increase in acid concentration. The mechanism of the HT reaction can be accounted for by the intracomplex HT reaction of the triplet exciplex 3(RNH3+...>CO)* with a rate constant of ca. 5 x 10(6) s-1. At higher acid concentrations, the triplet complex is decomposed by protonation to give free 3RNH3+* and BP, resulting in suppression of the rate for the HT reaction.

  DOI：

  10.1021/j100167a025
• 作为产物：
  描述：

  羟基-二苯基-甲基 、 2-萘胺 生成 二苯甲酮 、 2-naphthylammonium ion
  参考文献：
  名称：

  激光闪光光解法研究三重态2-萘基铵离子向二苯甲酮的氢原子转移反应：显着的质子效应

  摘要：

  The laser flash photolysis study at 355 nm in the 2-naphthylammonium ion (RNH3+) and benzophenone (BP) system has been carried out in methanol-water (9:1 v/v) at 290 K. At first, triplet benzophenone (3BP*) produced by fast intersystem crossing of 1BP* excited at 355 nm is quenched by RNH3+ with almost diffusion-controlled rates (1.1 x 10(10) M-1 s-1 at [H2SO4] = 0.015 M; 3.9 x 10(9) M-1 s-1 at [H2SO4] = 0.5 M). The triplet 2-naphthylammonium ion (3RNH3+*) is produced in the nanosecond region by triplet energy transfer from 3BP* to RNH3+ with efficiencies of 0.41 ([H2SO4] = 0.015 M) and 0.33 ([H2SO4] = 0.5 M) at [RNH3+] = 3.0 x 10(-3) M and at [BP] = 1.12 x 10(-2) M, competing with hydrogen abstraction of 3BP* from solvent (methanol) or RNH3+ molecules. Subsequently, in the microsecond region the hydrogen atom transfer (HT) reaction from 3RNH3+* to ground BP occurs effectively to give the naphthylamine cation radical (RNH2.+) and the ketyl radical (> COH). The decay rate (tau-obsd)-1 of 3RNH3+* increases with an increase of the BP concentration, and at higher BP concentrations a leveling off is observed. The (tau-obsd)-1 value decreases drastically with an increase in acid concentration. The mechanism of the HT reaction can be accounted for by the intracomplex HT reaction of the triplet exciplex 3(RNH3+...>CO)* with a rate constant of ca. 5 x 10(6) s-1. At higher acid concentrations, the triplet complex is decomposed by protonation to give free 3RNH3+* and BP, resulting in suppression of the rate for the HT reaction.

  DOI：

  10.1021/j100167a025

文献信息

• Laser flash photolysis study on the hydrogen atom transfer reaction from triplet 2-naphthylammonium ion to benzophenone: remarkable proton effect
  作者：Seiji Kohno、Mikio Hoshino、Haruo Shizuka

  DOI：10.1021/j100167a025

  日期：1991.7

  The laser flash photolysis study at 355 nm in the 2-naphthylammonium ion (RNH3+) and benzophenone (BP) system has been carried out in methanol-water (9:1 v/v) at 290 K. At first, triplet benzophenone (3BP*) produced by fast intersystem crossing of 1BP* excited at 355 nm is quenched by RNH3+ with almost diffusion-controlled rates (1.1 x 10(10) M-1 s-1 at [H2SO4] = 0.015 M; 3.9 x 10(9) M-1 s-1 at [H2SO4] = 0.5 M). The triplet 2-naphthylammonium ion (3RNH3+*) is produced in the nanosecond region by triplet energy transfer from 3BP* to RNH3+ with efficiencies of 0.41 ([H2SO4] = 0.015 M) and 0.33 ([H2SO4] = 0.5 M) at [RNH3+] = 3.0 x 10(-3) M and at [BP] = 1.12 x 10(-2) M, competing with hydrogen abstraction of 3BP* from solvent (methanol) or RNH3+ molecules. Subsequently, in the microsecond region the hydrogen atom transfer (HT) reaction from 3RNH3+* to ground BP occurs effectively to give the naphthylamine cation radical (RNH2.+) and the ketyl radical (> COH). The decay rate (tau-obsd)-1 of 3RNH3+* increases with an increase of the BP concentration, and at higher BP concentrations a leveling off is observed. The (tau-obsd)-1 value decreases drastically with an increase in acid concentration. The mechanism of the HT reaction can be accounted for by the intracomplex HT reaction of the triplet exciplex 3(RNH3+...>CO)* with a rate constant of ca. 5 x 10(6) s-1. At higher acid concentrations, the triplet complex is decomposed by protonation to give free 3RNH3+* and BP, resulting in suppression of the rate for the HT reaction.