Synthesis and characterization of a new fluorescent Zwitterionic spirocyclic meisenheimer complex of 1,3,5-trinitrobenzene

被引：22

作者：

Al-Kaysi, RO

Guirado, G

Valente, EJ

机构：

[1] Univ Rochester, Dept Chem, Rochester, NY 14627 USA

[2] CNRS, CEMES, GNS, F-31055 Toulouse, France

[3] Mississippi Coll, Dept Chem & Biochem, Clinton, MS 39058 USA

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 2004卷 / 16期

关键词：

nucleophilic aromatic substitution; zwitterions; Meisenheimer complexes; fluorescence spectroscopy; picric acid;

D O I：

10.1002/ejoc.200400260

中图分类号：

O62 [有机化学];

学科分类号：

070303 [有机化学]; 081704 [应用化学];

摘要：

In this communication we present the first stable zwitterionic spirocyclic Meisenheimer compound based on an N --> N rearrangement in the reaction between picric acid and diisopropylcarbodiimide. The structure was confirmed by single-crystal X-ray diffraction. Furthermore, this compound exhibits interesting fluorescence properties (phi(f) = 0.4-0.5), not shared with a typical Meisenheimer complex, and a fluorescence lifetime (tau = 9.1 ns) in dichloromethane. (C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004.

引用

收藏

页码：3408 / 3411

页数：4

相关论文

共 55 条

[1]

SOME ASPECTS OF ANIONIC SIGMA-COMPLEXES [J].

ARTAMKINA, GA ;

EGOROV, MP ;

BELETSKAYA, IP .

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

[2]

META BRIDGING REACTIONS OF ELECTRON-DEFICIENT AROMATICS .1. STUDIES DIRECTED TOWARD A ONE-STEP SYNTHESIS OF 6,7-BENZOMORPHAN RING-SYSTEM - FACILE PREPARATION OF POTENTIAL NARCOTIC-ANTAGONISTS [J].

BARD, RR ;

STRAUSS, MJ .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (13) :3789-3798

[3]

BERGMAN E, 1970, J CHEM SOC CHEM COMM, P511

[4]

INTERMEDIATES IN NUCLEOPHILIC AROMATIC SUBSTITUTION .3. VISIBLE ABSORPTION SPECTRA OF ACID AND BASIC FORM OF 1,3,5-TRINITROBENZENE-PIPERIDINE MEISENHEIMER COMPLEX IN 10 PERCENT DIOXANE-90 PERCENT WATER [J].

BERNASCO.CF .

JOURNAL OF ORGANIC CHEMISTRY, 1970, 35 (04) :1214-&

[5]

INTERMEDIATES IN NUCLEOPHILIC AROMATIC-SUBSTITUTION .11. SPIRO MEISENHEIMER COMPLEX OF N,N'-DIMETHYL-N-PICRYLETHYLENEDIAMINE - PARTIALLY RATE-LIMITING PROTON-TRANSFER OF COMPLEX-FORMATION - TEMPERATURE-JUMP STUDY [J].

BERNASCONI, CF ;

GEHRIGER, CL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1974, 96 (04) :1092-1099

[6]

INTERMEDIATES IN NUCLEOPHILIC AROMATIC SUBSTITUTION .2. TEMPERATURE-JUMP STUDY OF INTERACTION OF 1,3,5-TRINITROBENZENE WITH ALIPHATIC AMINES IN 10 PERCENT DIOXANE-90 PERCENT WATER . CONCURRENT NUCLEOPHILIC ATTACK ON AROMATIC CARBON AND ON NITRO GROUP [J].

BERNASCONI, CF .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1970, 92 (01) :129-+

[7]

INTERMEDIATES IN NUCLEOPHILIC AROMATIC-SUBSTITUTION .16. TOWARD A COMPLETE CHARACTERIZATION OF MECHANISM OF NUCLEOPHILIC AROMATIC-SUBSTITUTION BY AN AMINE - KINETICS OF SPIRO MEISENHEIMER COMPLEXES DERIVED FROM N-METHYLETHANOLAMINE [J].

BERNASCONI, CF ;

GEHRIGER, CL ;

ROSSI, RHD .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1976, 98 (26) :8451-8459

[8]

INTERMEDIATES IN NUCLEOPHILIC AROMATIC-SUBSTITUTION .14. SPIRO MEISENHEIMER COMPLEXES DERIVED FROM N,N'-DIMETHYLETHYLENEDIAMINE - KINETICS IN AQUEOUS DIMETHYL-SULFOXIDE [J].

BERNASCONI, CF ;

TERRIER, F .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1975, 97 (26) :7458-7466

[9]

INTERMEDIATES IN NUCLEOPHILIC AROMATIC-SUBSTITUTION .20. RATE-LIMITING PROTON-TRANSFER IN THE FORMATION OF MEISENHEIMER COMPLEXES BETWEEN 1,3,5-TRINITROBENZENE AND AMINES - EFFECT OF DIMETHYL-SULFOXIDE ON PROTON-TRANSFER RATES - RELATIVE LEAVING-GROUP ABILITIES OF AMINES AND ALKOXIDE IONS [J].

BERNASCONI, CF ;

MULLER, MC ;

SCHMID, P .

JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (18) :3189-3196

[10]

Formation and stability of zwitterionic complexes between nitrobenzofuroxans and amines [J].

Boga, C ;

Forlani, L .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 2001, (08) :1408-1413

← 1 2 3 4 5 6 →