N-methyl-9-phenylacridinium cation | 42206-02-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: N-methyl-9-phenylacridinium cation
• 英文别名: 10-methyl-9-phenylacridinium ion；N-methyl-9-phenylacridinium salt；10-methyl-9-phenylacridinium；N-methyl-9-phenyl-acridinium；N-methyl-6-phenylacridinium；10-methyl-9-phenyl-acridinium；10-Methyl-9-phenylacridin-10-ium
• CAS: 42206-02-0
• 化学式: C₂₀H₁₆N
• 分子量: 270.354
• InChiKey: OPOTWUHKVSPPBY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  3.9
• 氢给体数：
  0
• 氢受体数：
  0

反应信息

• 作为反应物：
  描述：

  N-methyl-9-phenylacridinium cation 在 sodium tetrahydroborate 作用下， 以 乙醇 为溶剂， 反应 2.0h， 以85%的产率得到10-methyl-9-phenyl-9,10-dihydroacridine
  参考文献：
  名称：

  Toward Organic Photohydrides: Excited-State Behavior of 10-Methyl-9-phenyl-9,10-dihydroacridine

  摘要：

  The excited-state hydride release from 10methyl-9-phenyl-9,10-dihydroacridine (PhAcrH) was investigated using steady-state and time-resolved UV/vis absorption spectroscopy. Upon excitation, PhAcrH is oxidized to the corresponding iminium ion (PhAcr(+)), while the solvent (acetonitrile/water mixture) is reduced (52% of PhAcr(+) and 2.5% of hydrogen is formed). The hydride release occurs from the triplet excited state by a stepwise electron/hydrogen-atom transfer mechanism. To facilitate the search for improved organic photohydrides that exhibit a concerted mechanism, a computational methodology is presented that evaluates the thermodynamic parameters for the hydride ion, hydrogen atom, and electron release from organic hydrides.

  DOI：

  10.1021/jp401770e
• 作为产物：
  描述：

  9-苯基-9-乙氧基-10-甲基吖啶 以 甲醇 为溶剂， 生成 N-methyl-9-phenylacridinium cation
  参考文献：
  名称：

  Grigor'eva, T. M.; Ivanov, V. L.; Kuz'min, M. G., Journal of Organic Chemistry USSR (English Translation), 1981, vol. 17, # 2, p. 362 - 367

  摘要：

  DOI：

文献信息

• Effects of Metal Ions on Physicochemical Properties and Redox Reactivity of Phenolates and Phenoxyl Radicals: Mechanistic Insight into Hydrogen Atom Abstraction by Phenoxyl Radical−Metal Complexes
  作者：Shinobu Itoh、Hideyuki Kumei、Shigenori Nagatomo、Teizo Kitagawa、Shunichi Fukuzumi

  DOI：10.1021/ja0036110

  日期：2001.3.1

  complexes are also influenced by the metal ions, depending on the Lewis acidity of the metal ions. The phenoxyl radical complexes are successfully generated in situ by the oxidation of the phenolate complexes with (NH4)(2)[Ce4+(NO3)6] (CAN). They exhibited strong absorption bands around 400 nm together with a broad one around 600-900 nm, the latter of which is also affected by the metal ions. The phenoxyl

  使用2,4-二叔丁基-6-(1,4,7,10-tetraoxa -13-aza-cyclopentadec-13-ylmethyl)phenol (L1H) 和 2,4-di-tert-butyl-6-(1,4,7,10,13-pentaoxa-16-aza-cyclooctadec-16-ylmethyl) )苯酚 (L2H) 以检查阳离子对苯酚盐和苯氧基自由基复合物的结构、物理化学性质和氧化还原反应性的影响。通过X射线晶体学分析确定了L1-的Mg2+-和Ca2+-配合物以及L2-的Ca2+-和Sr2+-配合物的晶体结构，表明Ca2+-配合物中的冠醚环从平面性，而 Mg2+- 和 Sr2+- 络合物中的那些是相当平坦的。取决于金属离子的路易斯酸度，酚盐配合物的光谱特征 (UV-vis) 以及氧化还原电位也受金属离子的影响。通过用 (NH4)(2)[Ce4+(NO3)6] (CAN) 氧化
• A classical but new kinetic equation for hydride transfer reactions
  作者：Xiao-Qing Zhu、Fei-Huang Deng、Jin-Dong Yang、Xiu-Tao Li、Qiang Chen、Nan-Ping Lei、Fan-Kun Meng、Xiao-Peng Zhao、Su-Hui Han、Er-Jun Hao、Yuan-Yuan Mu

  DOI：10.1039/c3ob40831k

  日期：——

  activation energies of various hydride transfer reactions was developed according to transition state theory using the Morse-type free energy curves of hydride donors to release a hydride anion and hydride acceptors to capture a hydride anion and by which the activation energies of 187 typical hydride self-exchange reactions and more than thirty thousand hydride cross transfer reactions in acetonitrile were

  根据过渡态理论，使用氢化物​​供体的莫尔斯型自由能曲线释放氢化物阴离子和氢化物受体以捕获氢化物阴离子，开发了一种经典但新颖的动力学方程式，用于估算各种氢化物转移反应的活化能。 187个典型的氢化物自交换反应和超过3万个氢化物交叉转移反应的活化能 乙腈被安全地估计在这项工作中。由于动力学方程式的发展仅基于氢化物转移反应物的相关化学键变化，因此该动力学方程式也应适用于质子转移反应，氢原子转移反应以及所有其他涉及断裂和化学反应的化学反应。化学键的形成。这项工作最重要的贡献之一是实现了氢化物转移反应动力学方程和热力学方程的完美统一。
• Hydride-Transfer Reaction to a Mononuclear Manganese(III) Iodosylarene Complex
  作者：Donghyun Jeong、Jaeheung Cho

  DOI：10.1021/acs.inorgchem.1c00562

  日期：2021.6.7

  Metal iodosylarene species have received interest because of their potential oxidative power as a catalyst. We present the first example of hydride-transfer reactions to a mononuclear manganese(III) iodosylbenzene complex, [MnIII(TBDAP)(OIPh)(OH)]2+ (1; TBDAP = N,N-di-tert-butyl-2,11-diaza[3.3](2,6)pyridinophane), with dihydronicotinamide adenine dinucleotide (NADH) analogues. Kinetic studies show

  金属碘代芳烃物种因其作为催化剂的潜在氧化能力而受到关注。我们提出氢化物转移反应的单核锰（III）亚碘酰苯的第一示例络合物，[锰III（TBDAP）（OIPh）（OH）] 2+（1 ; TBDAP = Ñ，ñ -二叔丁基- 2,11-二氮杂[3.3](2,6)吡啶烷)，与二氢烟酰胺腺嘌呤二核苷酸(NADH)类似物。动力学研究表明，从 NADH 类似物到1 的氢化物转移是通过质子耦合电子转移发生的，然后是快速电子转移。
• Excited-State Hydroxide Ion Release From a Series of Acridinol Photobases
  作者：Yun Xie、Stefan Ilic、Sanja Skaro、Veselin Maslak、Ksenija D. Glusac

  DOI：10.1021/acs.jpca.6b10980

  日期：2017.1.19

  parameters that control the reaction barriers, the kinetics of excited-state OH– release from a series of acridinol photobases were studied using transient absorption spectroscopy. The rate constants were obtained in three solvents (methanol, butanol, and isobutanol), and the data were modeled using Marcus theory. The intrinsic reorganization energies obtained from these fits were found to correlate

  基于acridinol衍生物引线的激发态heterolysis与OH的释放-离子和相应的吖啶鎓阳离子的形成。为了评估该控制反应的障碍的参数，激发态OH的动力学-使用瞬态吸收光谱从一系列acridinol photobases的释放进行了研究。在三种溶剂（甲醇，丁醇和异丁醇）中获得速率常数，并使用Marcus理论对数据进行建模。从这些拟合中获得的内在重组能被发现与使用介电连续谱模型计算出的溶剂重组能很好地相关，这表明激发态OH –沿溶剂反应坐标发生释放。此外，使用丙二酸二甲酯和硝基苯乙烯之间的迈克尔反应证明了cri啶醇光碱发生光引发化学反应的能力。
• Simple and modular design platform of bimodal turn-on chemodosimeters for oxophilic metal cations
  作者：David T. Hogan、Todd C. Sutherland

  DOI：10.1039/c8nj04198a

  日期：——

  Three chemodosimeters that exhibit up to 3000-fold enhancement in turn-on visible colour and emission in the presence of oxophilic metal cations.

  三种化学传感器在氧亲合性金属阳离子存在时表现出高达3000倍的开启可见颜色和发射增强。