Application of electrospray ionization mass spectrometry for studies of anionic σ-adducts of aromatic nitrocompounds

被引：16

作者：

Danikiewicz, W ^{[1
]}

Bienkowski, T ^{[1
]}

Wojciechowski, K ^{[1
]}

机构：

[1] Polish Acad Sci, Inst Organ Chem, PL-01224 Warsaw, Poland

来源：

TETRAHEDRON LETTERS | 2004年 / 45卷 / 05期

关键词：

anionic sigma-adducts; aromatic nitro compounds; carbanions; electrospray mass spectrometry; mass spectrometry fragmentation;

D O I：

10.1016/j.tetlet.2003.11.094

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

It has been found that anionic sigma-adducts formed in the reactions of highly electrophilic nitroarenes with selected carbanions, alkoxide anions and amines can be transferred to the gas phase using an electrospray ion source and the resulting ions can be studied using various mass spectrometry techniques in the solvent-free environment. This method can also be used for estimating the relative equilibrium constants of the sigma-adduct formation reactions in a liquid phase. (C) 2003 Elsevier Ltd. All rights reserved.

引用

页码：931 / 934

页数：4

共 13 条

[1]

[Anonymous], 1991, NUCLEOPHILIC AROMATI

[2] SOME ASPECTS OF ANIONIC SIGMA-COMPLEXES [J].

ARTAMKINA, GA ;

EGOROV, MP ;

BELETSKAYA, IP .

CHEMICAL REVIEWS, 1982, 82 (04) :427-459

[3] 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

[4] CHARACTERIZATION OF EXPLOSIVES BY LIQUID-CHROMATOGRAPHY MASS-SPECTROMETRY AND LIQUID-CHROMATOGRAPHY TANDEM MASS-SPECTROMETRY USING ELECTROSPRAY-IONIZATION AND PARENT-ION SCANNING TECHNIQUES [J].

CASETTA, B ;

GAROFOLO, F .

ORGANIC MASS SPECTROMETRY, 1994, 29 (10) :517-525

[5]

Cole R.B., 1997, Electrospray Ionization Mass Spectrometry

[6] Kinetic and equilibrium studies of sigma-adduct formations and nucleophilic substitution in the reactions of trinitro-activated benzenes with aliphatic amines in acetonitrile [J].

Crampton, MR ;

Lord, SD .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1997, (02) :369-376

[7] POLYCYCLIC AROMATIC-COMPOUNDS OF ENVIRONMENTAL AND OCCUPATIONAL IMPORTANCE - THEIR OCCURRENCE, TOXICITY AND THE DEVELOPMENT OF HIGH-PURITY CERTIFIED REFERENCE MATERIALS .3. [J].

JACOB, J ;

KARCHER, W ;

BELLIARDO, JJ ;

DUMLER, R ;

BOENKE, A .

FRESENIUS JOURNAL OF ANALYTICAL CHEMISTRY, 1991, 340 (12) :755-767

[8]

KOPPEL IA, 2000, J CHEM SOC P2, P1125, DOI DOI 10.1039/B001792M

[9] Inhibition of octopus glutathione transferase by Meisenheimer complex analog, S-(2,4,6-trinitrophenyl) glutathione [J].

Liou, JY ;

Huang, TM ;

Chang, GG .

JOURNAL OF PROTEIN CHEMISTRY, 2000, 19 (07) :615-620

[10]

Pramanik BirendraN., 2002, APPL ELECTROSPRAY MA

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