Ambident reactivity of the nitrite ion revisited

被引：46
|
作者：
Tishkov, AA
Schmidhammer, U
Roth, S
Riedle, E
Mayr, H
机构：
[1] Univ Munich, Dept Chem & Biochem, D-81377 Munich, Germany
[2] Univ Munich, Lehrstuhl Biomol Opt, D-80538 Munich, Germany
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2005年 / 44卷 / 29期
关键词：
HSAB principle; kinetics; Klopman-Salem equation; Kornblum's rule; nitro compounds;
D O I：
10.1002/anie.200501274
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
(Chemical Equation Presented) Lost control: The rationalization of the ambident reactivity of NO2- by the change between charge control to orbital control has to be revised. SN1-type reactions of carbocations with NO2- give kinetically controlled product mixtures only when these reactions proceed without activation energy (diffusion control). Activation-controlled SN1 alkylations are reversible and lead to the thermodynamically more stable nitro compounds. © 2005 Wiley-VCH Verlag GmbH &Co. KGaA.
引用
收藏
页码：4623 / 4626
页数：4
相关论文
共 50 条
  • [31] REACTIVITY OF AMBIDENT ANIONS . ETHYLATION OF ACETYLACETONE METALLIC ENOLATES
    KURTS, AL
    GENKINA, NK
    BELETSKA.IP
    REUTOV, OA
    DOKLADY AKADEMII NAUK SSSR, 1969, 188 (03): : 597 - &
  • [32] Nitrite Reactivity with Magnetite
    Dhakal, P.
    Matocha, C. J.
    Huggins, F. E.
    Vandiviere, M. M.
    ENVIRONMENTAL SCIENCE & TECHNOLOGY, 2013, 47 (12) : 6206 - 6213
  • [33] AMBIDENT REACTIVITY OF THE IMIDAZOLATE ANION TOWARDS AN AROMATIC ELECTROPHILE
    TERRIER, F
    DEBLEDS, F
    HALLE, JC
    SIMONNIN, MP
    TETRAHEDRON LETTERS, 1982, 23 (40) : 4079 - 4082
  • [34] THE REACTIVITY OF INTERMEDIATES IN NON-ENZYMIC BROWNING REACTIONS TOWARDS NITRITE ION
    WEDZICHA, BL
    HILL, D
    COCKSHOTT, JB
    JOURNAL OF THE SCIENCE OF FOOD AND AGRICULTURE, 1982, 33 (03) : 306 - 308
  • [35] Alkylation of the ambident indole ion in ionic liquids
    G. Vavilina
    A. Zicmanis
    S. Drozdova
    P. Mekss
    M. Klavins
    Chemistry of Heterocyclic Compounds, 2008, 44 : 530 - 541
  • [36] ALKYLATION OF THE AMBIDENT INDOLE ION IN IONIC LIQUIDS
    Vavilina, G.
    Zicmanis, A.
    Drozdova, S.
    Mekss, P.
    Klavins, M.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (05) : 530 - 541
  • [37] L-ASCORBATE ION AS AN AMBIDENT NUCLEOPHILE
    BUNCEL, E
    JACKSON, KGA
    JONES, JKN
    CHEMISTRY & INDUSTRY, 1965, (02) : 89 - &
  • [38] GAS-PHASE AMBIDENT REACTIVITY OF ACYCLIC ENOLATE ANIONS
    FRERIKS, IL
    DEKONING, LJ
    NIBBERING, NMM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (24) : 9119 - 9124
  • [39] Ambident Reactivity of Nitroso Compounds for Direct Amination and Hydroxylation of Carbonyls
    Dana, Suman
    Ramakrishna, Isai
    Baidya, Mahiuddin
    SYNTHESIS-STUTTGART, 2017, 49 (15): : 3281 - 3290
  • [40] REACTIVITY OF PHOSPHORAMIDATES - ALKYLATION OF LITHIUM PHOSPHORAMIDOTHIOATES - EVIDENCE FOR AN AMBIDENT ANION
    DREUX, M
    SAVIGNAC, P
    COMPTES RENDUS HEBDOMADAIRES DES SEANCES DE L ACADEMIE DES SCIENCES SERIE C, 1975, 280 (05): : 297 - 299
12345