Intrinsic barrier for protonation of radical anions

被引：5
作者：
Rozental, Esther [1 ]
Hoz, Shmaryahu [1 ]
机构：
[1] Bar Ilan Univ, Dept Chem, IL-52900 Ramat Gan, Israel
来源：
TETRAHEDRON | 2009年 / 65卷 / 52期
关键词：
Radical anion; Protonation; Intrinsic barrier; Marcus equation; ACRYLAMIDE DERIVATIVES; ELECTRON ADDUCTS; GAS-PHASE; SMI2; REDUCTION; DONORS; ACID;
D O I：
10.1016/j.tet.2009.10.092
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Ab initio calculations on radical anions show that. counterintuitively, protonation on the radicaloid carbon is favored. In the case of radical anions derived from acrylonitrile and acrylaldehyde, protonation on the heteroatom is less favored than protonation on the radicaloid carbon. However, in nitroethylene, the preferred protonation site is on the nitro oxygen in accordance with experimental observation. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：10945 / 10949
页数：5
相关论文
共 50 条
  • [41] Cyanocyclopentadiene-Annulated Polycyclic Aromatic Radical Anions: Predicted Negative Ion Photoelectron Spectra and Singlet-Triplet Energies of Cyanoindene and Cyanofluorene Radical Anions
    Abeysooriya, Dushmantha N. Koku Hannadige
    White, Nolan J.
    Workman, Kie T.
    Dupuy, Jonathan A.
    Gichuhi, Wilson K.
    JOURNAL OF PHYSICAL CHEMISTRY A, 2024, 128 (10) : 1837 - 1852
  • [42] STEREOSELECTIVE PROTONATION OF CARBANIONS .3. 1,3-DIOXOLAN-4-ONES AND 1,3-OXAZOLIDINE-4-ONES - SYNTHESES AND DIASTEREOSELECTIVE PROTONATION OF THEIR ANIONS
    HUNIG, S
    KEITA, Y
    PETERS, K
    VONSCHNERING, HG
    CHEMISCHE BERICHTE, 1994, 127 (08) : 1495 - 1500
  • [43] Dual Character of Excited Radical Anions in Aromatic Diimide Bis(radical anion)s: Donor or Acceptor?
    Lu, Chao
    Fujitsuka, Mamoru
    Sugimoto, Akira
    Majima, Tetsuro
    JOURNAL OF PHYSICAL CHEMISTRY C, 2017, 121 (08) : 4558 - 4563
  • [44] Hydroxyl radical production by abiotic oxidation of pyrite under estuarine conditions: The effects of aging, seawater anions and illumination
    Liu, Ruixue
    Dai, Yinshun
    Feng, Yucheng
    Sun, Shiwen
    Zhang, Xiaodong
    An, Chunjiang
    Zhao, Shan
    JOURNAL OF ENVIRONMENTAL SCIENCES, 2024, 135 : 715 - 727
  • [45] Chemical doping of unsubstituted perylene diimide to create radical anions with enhanced stability and tunable photothermal conversion efficiency
    Che, Canyan
    Tong, Shaohua
    Jia, Yanhua
    Yang, Jiaji
    He, Xiandong
    Han, Shaobo
    Jiang, Qinglin
    Ma, Yuguang
    FRONTIERS IN CHEMISTRY, 2023, 11
  • [46] OD ESR Detection of the Radical Anions of Cyclic Nitrones in Liquid Solutions
    M. M. Barlukova
    V. A. Bagryansky
    N. P. Gritsan
    V. F. Starichenko
    I. A. Grigor'ev
    Yu. N. Molin
    Doklady Physical Chemistry, 2004, 397 : 184 - 186
  • [47] Didehydro radical anions from ketones via O•- chemical ionization
    Lin, MX
    Grabowski, JJ
    INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 2004, 237 (2-3) : 149 - 165
  • [48] Protonation-induced change in the conformation, crystal structure and property of triarylmethyl carbocation radical
    Zhang, Cong
    Feng, Ya
    Shen, Chen
    Yong, Guoping
    CHEMICAL PHYSICS LETTERS, 2016, 649 : 97 - 102
  • [49] Simultaneous Degradation, Dehalogenation, and Detoxification of Halogenated Antibiotics by Carbon Dioxide Radical Anions
    Ding, Yanzhou
    Yu, Xia
    Lyu, Shuguang
    Zhen, Huajun
    Zhao, Wentao
    Peng, Cheng
    Wang, Jiaxi
    Zhu, Yiwen
    Zhu, Chengfei
    Zhou, Lei
    Sui, Qian
    ENGINEERING, 2024, 37 : 78 - 86
  • [50] Excitation of Radical Anions of Naphthalene Diimides in Consecutive- and Electro-Photocatalysis
    Caby, Sofia
    Bouchet, Lydia M.
    Arguello, Juan E.
    Rossi, Roberto A.
    Bardagi, Javier, I
    CHEMCATCHEM, 2021, 13 (13) : 3001 - 3009
12345