Meisenheimer complexes positively characterized as stable intermediates in the gas phase

被引:66
作者
Chiavarino, Barbara
Crestoni, Maria Elisa
Fornarini, Simonetta
Lanucara, Francesco
Lemaire, Joel
Maitre, Philippe
机构
[1] Univ Roma La Sapienza, Dipartimento Studi Chim & Tecnol Sostanze Biol At, I-00185 Rome, Italy
[2] Univ Paris Sud 11, Fac Sci Orsay, Chim Phys Lab, UMR8000, F-91405 Orsay, France
关键词
anionic sigma complexes; IR spectroscopy; mass spectrometry; photodissociation; structure elucidation;
D O I
10.1002/anie.200604630
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
(Graph Presented) Proof positive: Infrared multiphoton dissociation (IRMPD) spectroscopy, with the tunable IR radiation of a free-electron laser source, provides positive identification of alkoxide adducts of 1,3,5-trinitrobenzene as prototypical anionic o complexes in the gas phase (see calculated IR spectrum of 1 under the experimental IRMPD spectrum; N blue, O green, Cgray, H light gray). © 2007 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码:1995 / 1998
页数:4
相关论文
共 37 条
[1]  
Asmis K.R., 2005, ANGEW CHEM, V117, P3182
[2]   Polyhedral vanadium oxide cages:: Infrared spectra of cluster anions and size-induced d electron localization [J].
Asmis, KR ;
Santambrogio, G ;
Brümmer, M ;
Sauer, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (20) :3122-3125
[3]   GAS-PHASE NUCLEOPHILIC REACTIONS OF AROMATIC SYSTEMS [J].
BRISCESE, SM ;
RIVEROS, JM .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (01) :230-231
[4]   AM1 STUDIES ON THE STABILITIES OF ANIONIC SIGMA-COMPLEX REGIOISOMERS - THERMODYNAMICS OF REGIOSELECTIVITY IN THE REACTION OF METHIDE, METHOXIDE, AND HYDROXIDE ANIONS WITH ELECTRON-DEFICIENT AROMATICS [J].
BUNCEL, E ;
TARKKA, RM ;
DUST, JM .
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1994, 72 (07) :1709-1721
[5]   RATIONALIZING THE REGIOSELECTIVITY IN POLYNITROARENE ANIONIC SIGMA-ADDUCT FORMATION - RELEVANCE TO NUCLEOPHILIC AROMATIC-SUBSTITUTION [J].
BUNCEL, E ;
DUST, JM ;
TERRIER, F .
CHEMICAL REVIEWS, 1995, 95 (07) :2261-2280
[6]   Meisenheimer complexes bonded at carbon and at oxygen [J].
Chen, H ;
Chen, HW ;
Cooks, RG .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 2004, 15 (07) :998-1004
[7]   Infrared spectroscopy of protonated phenylsilane in the gas phase [J].
Chiavarino, B ;
Crestoni, ME ;
Fornarini, S ;
Lemaire, J ;
Mac Aleese, L ;
Maître, P .
CHEMPHYSCHEM, 2005, 6 (03) :437-440
[8]   Desorption electrospray ionization of explosives on surfaces:: Sensitivity and selectivity enhancement by reactive desorption electrospray ionization [J].
Cotte-Rodríguez, I ;
Takáts, Z ;
Talaty, N ;
Chen, HW ;
Cooks, RG .
ANALYTICAL CHEMISTRY, 2005, 77 (21) :6755-6764
[9]   Generation and reactions of anionic σ-adducts of 1,3-dinitrobenzene and 1,3,5-trinitrobenzene with carbanions in a gas phase, using an electrospray ion source as the chemical reactor [J].
Danikiewicz, W ;
Bienkowski, T ;
Poddebniak, D .
JOURNAL OF THE AMERICAN SOCIETY FOR MASS SPECTROMETRY, 2004, 15 (06) :927-933
[10]   Application of electrospray ionization mass spectrometry for studies of anionic σ-adducts of aromatic nitrocompounds [J].
Danikiewicz, W ;
Bienkowski, T ;
Wojciechowski, K .
TETRAHEDRON LETTERS, 2004, 45 (05) :931-934