Bond dissociation energies for radical dimers derived from highly stabilized carbon-centered radicals

被引:110
|
作者
Frenette, M [1 ]
Aliaga, C [1 ]
Font-Sanchis, E [1 ]
Scaiano, JC [1 ]
机构
[1] Univ Ottawa, Dept Chem, Ottawa, ON K1N 6N5, Canada
关键词
D O I
10.1021/ol049111j
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The temperature dependence of the dissociation of dimers formed from highly stabilized carbon-centered radicals has been examined. Analysis of the data yields the bond dissociation energy (BDE) for the central head-to-head C-C bond in these compounds. For example, for the dimer derived from 3-phenyl-2-coumaranone, BDE is 23.6 kcal/mol and the C-C bond length 1.596 Angstrom, a rather long value for a or bond.
引用
收藏
页码:2579 / 2582
页数:4
相关论文
共 50 条
  • [1] Bond Dissociation Enthalpies of Large Aromatic Carbon-Centered Radicals
    Hemelsoet, Karen
    Van Speybroeck, Veronique
    Waroquier, Michel
    JOURNAL OF PHYSICAL CHEMISTRY A, 2008, 112 (51): : 13566 - 13573
  • [2] Formation, Isomerization, and Dissociation of α-Carbon-Centered and π-Centered Glycylglycyltryptophan Radical Cations
    Ng, Dominic C. M.
    Song, Tao
    Siu, S. O.
    Siu, C. K.
    Laskin, Julia
    Chut, Ivan K.
    JOURNAL OF PHYSICAL CHEMISTRY B, 2010, 114 (06): : 2270 - 2280
  • [3] Cyclization of a carbon-centered radical derived from oxaziridine cleavage
    Usuki, Yoshinosuke
    Peng, Xin
    Gulgeze, Belgin
    Manyem, Shankar
    Aube, Jeffrey
    ARKIVOC, 2006, : 189 - 199
  • [4] Formation, isomerization, and dissociation of ε- and α- carbon-centered tyrosylglycylglycine radical cations
    Lai, Cheuk-Kuen
    Mu, Xiaoyan
    Hao, Qiang
    Hopkinson, Alan C.
    Chu, Ivan K.
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2014, 16 (44) : 24235 - 24243
  • [5] Recent Advances in C-F Bond Formation from Carbon-Centered Radicals
    Zhang, Jihua
    Wang, Juanjuan
    Cheng, Qiang
    CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (09) : 1009 - 1031
  • [6] Rate constants for the β-elimination of tosyl radical from a variety of substituted carbon-centered radicals
    Timokhin, VI
    Gastaldi, S
    Bertrand, MP
    Chatgilialoglu, C
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (09): : 3532 - 3537
  • [7] Radical ring closures of 4-isocyanato carbon-centered radicals
    Minin, PL
    Walton, JC
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (07): : 2960 - 2963
  • [8] Bond dissociation energies and radical stabilization energies associated with substituted methyl radicals
    Henry, DJ
    Parkinson, CJ
    Mayer, PM
    Radom, L
    JOURNAL OF PHYSICAL CHEMISTRY A, 2001, 105 (27): : 6750 - 6756
  • [9] Tetraarylsuccinonitriles as mechanochromophores to generate highly stable luminescent carbon-centered radicals
    Sumi, Toshikazu
    Goseki, Raita
    Otsuka, Hideyuki
    CHEMICAL COMMUNICATIONS, 2017, 53 (87) : 11885 - 11888
  • [10] Lactone-derived carbon-centered radicals: Formation and reactivity with oxygen
    Bejan, EV
    Font-Sanchis, E
    Scaiano, JC
    ORGANIC LETTERS, 2001, 3 (25) : 4059 - 4062