Parr's index to describe both electrophilicity and nucleophilicity

被引:46
|
作者
Kiyooka, Syun-ichi [1 ]
Kaneno, Daisuke [1 ]
Fujiyama, Ryoji [1 ]
机构
[1] Kochi Univ, Dept Mat Sci, Fac Sci, Kochi 7808520, Japan
关键词
Parr's omega index; Single reactivity scale; Electrophilicity; Nucleophilicity; HOMO and LUMO; ELECTRONIC THEORY; ORBITAL THEORY; REACTIVITY; HARDNESS;
D O I
10.1016/j.tetlet.2012.11.039
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We have disclosed a new aspect of Parr's omega value (omega = mu(2)/2 eta), which was originally proposed as an electrophilicity index, and reformed the omega value as a useful single scale from electrophilicity to nucleophilicity by introducing the corresponding epsilon values (epsilon = mu eta). The plot of the to values against the 8 values (omega-epsilon correlation) presented a fine parabola for 65 chemical species: the order of the electrophilicity is seen at negative epsilon values and the order of nucleophilicity is seen at positive a values. (C) 2012 Elsevier Ltd. All rights reserved.
引用
收藏
页码:339 / 342
页数:4
相关论文
共 50 条
  • [31] A comparative study to predict regioselectivity, electrophilicity and nucleophilicity with Fukui function and Hirshfeld charge
    Wang, Bin
    Rong, Chunying
    Chattaraj, Pratim K.
    Liu, Shubin
    THEORETICAL CHEMISTRY ACCOUNTS, 2019, 138 (12)
  • [32] Hirshfeld Charge as a Quantitative Measure of Electrophilicity and Nucleophilicity: Nitrogen-Containing Systems
    Zhou Xia-Yu
    Rong Chun-Ying
    Lu Tian
    Liu Shu-Bin
    ACTA PHYSICO-CHIMICA SINICA, 2014, 30 (11) : 2055 - 2062
  • [33] A comparative study to predict regioselectivity, electrophilicity and nucleophilicity with Fukui function and Hirshfeld charge
    Bin Wang
    Chunying Rong
    Pratim K. Chattaraj
    Shubin Liu
    Theoretical Chemistry Accounts, 2019, 138
  • [34] Nucleophilicity and electrophilicity of silylenes from a molecular electrostatic potential and dual descriptor perspectives
    Correa, Jose V.
    Jaque, Pablo
    Olah, Julianna
    Toro-Labbe, Alejandro
    Geerlings, Paul
    CHEMICAL PHYSICS LETTERS, 2009, 470 (4-6) : 180 - 186
  • [35] Quantitative characterization of group electrophilicity and nucleophilicity for intramolecular Diels-Alder reactions
    Soto-Delgado, Jorge
    Domingo, Luis R.
    Contreras, Renato
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2010, 8 (16) : 3678 - 3683
  • [36] Revisiting electroaccepting and electrodonating powers: proposals for local electrophilicity and local nucleophilicity descriptors
    Morell, Christophe
    Gazquez, Jose L.
    Vela, Alberto
    Guegan, Frederic
    Chermette, Henry
    PHYSICAL CHEMISTRY CHEMICAL PHYSICS, 2014, 16 (48) : 26832 - 26842
  • [37] Update 1 of: Electrophilicity Index
    Chattaraj, Pratim Kumar
    Roy, Debesh Ranjan
    CHEMICAL REVIEWS, 2007, 107 (09) : PR46 - PR74
  • [38] Automated quantum chemistry for estimating nucleophilicity and electrophilicity with applications to retrosynthesis and covalent inhibitors
    Ree, Nicolai
    Goeller, Andreas H.
    Jensen, Jan H.
    DIGITAL DISCOVERY, 2024, 3 (02): : 347 - 354
  • [39] An Experimental Radical Electrophilicity Index
    Santschi, Nico
    Nauser, Thomas
    CHEMPHYSCHEM, 2017, 18 (21) : 2973 - 2976
  • [40] Update 2 of: Electrophilicity Index
    Chattaraj, Pratim Kumar
    Giri, Santanab
    Duley, Soma
    CHEMICAL REVIEWS, 2011, 111 (02) : PR43 - PR75