Charge-tagged N-heterocyclic carbenes

被引：29
作者：
Corilo, Yuri E. [1 ]
Nachtigall, Fabiane M. [1 ]
Abdelnur, Patricia V. [1 ]
Ebeling, Gunter [2 ]
Dupont, Jairton [2 ]
Eberlin, Marcos N. [1 ]
机构：
[1] Univ Estadual Campinas, Inst Chem, ThoMSon Mass Spectrometry Lab, UNICAMP, BR-13083970 Campinas, SP, Brazil
[2] Univ Fed Rio Grande do Sul, Inst Chem, Lab Mol Catalysis, BR-91501970 Porto Alegre, RS, Brazil
来源：
RSC ADVANCES | 2011年 / 1卷 / 01期
基金：
巴西圣保罗研究基金会;
关键词：
IMIDAZOLIUM IONIC LIQUIDS; ELECTROSPRAY-IONIZATION MASS; GAS-PHASE; MECHANISM; SPECTROMETRY; STABILITY; COMPLEXES; CATIONS; PROBES; SALTS;
D O I：
10.1039/c1ra00024a
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The interception, formation and characterization of the first stable, long lived charge-tagged N-heterocyclic carbenes of the general type 4(x+) (x = 1-3) and analogues is reported. Via ESI(+)-MS of solutions of bromine salts of doubly, triply and quadruply charged imidazolium ion IL (3. Br-n, n = 2-4), the isolated 4(x+) as well as charged aggregates [3.Br(n-x)](x+) likely to be participating in the [3.Br(n-x)](x+) reversible arrow 4(x+) + HBr solution equilibrium could be transferred and characterized in the gas phase. Mimicking the solution equilibrium, the gaseous [3.Br(n-x)](x+) were found to dissociate nearly exclusively via HBr loss during thermal activation via collisions to form gaseous 4(x+), which were found to add to acrolein and acetone.
引用
收藏
页码：73 / 78
页数：6
相关论文
共 53 条
  • [21] Using geminal dicationic ionic liquids as solvents for high-temperature organic reactions
    Han, XX
    Armstrong, DW
    [J]. ORGANIC LETTERS, 2005, 7 (19) : 4205 - 4208
  • [22] Herrmann WA, 2002, ANGEW CHEM INT EDIT, V41, P1290, DOI 10.1002/1521-3773(20020415)41:8<1290::AID-ANIE1290>3.0.CO
  • [23] 2-Y
  • [24] Hinderling C, 1998, ANGEW CHEM INT EDIT, V37, P2685, DOI 10.1002/(SICI)1521-3773(19981016)37:19<2685::AID-ANIE2685>3.0.CO
  • [25] 2-M
  • [26] Reactions of a stable (phosphanyl)(silyl)carbene with aliphatic aldehydes:: [2+1] versus [2+2] addition to a carbonyl group
    Illa, O
    Gornitzka, H
    Branchadell, V
    Baceiredo, A
    Bertrand, G
    Ortuño, RM
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2003, 2003 (16) : 3147 - 3152
  • [27] Biomimetic approaches to gas phase peptide chemistry: combining selective binding motifs with reactive carbene precursors to form molecular mousetraps
    Julian, RR
    May, JA
    Stoltz, BM
    Beauchamp, JL
    [J]. INTERNATIONAL JOURNAL OF MASS SPECTROMETRY, 2003, 228 (2-3) : 851 - 864
  • [28] A highly enantioselective catalytic intramolecular Stetter reaction
    Kerr, MS
    de Alaniz, JR
    Rovis, T
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (35) : 10298 - 10299
  • [29] Kirmse W., 1971, Carbene Chemistry
  • [30] Insights Into the Carbene-Initiated Aggregation of [Fe(cot)2]
    Lavallo, Vincent
    El-Batta, Amer
    Bertrand, Guy
    Grubbs, Robert H.
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2011, 50 (01) : 268 - 271
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