Formation and stability of zwitterionic complexes between nitrobenzofuroxans and amines

被引:40
作者
Boga, C [1 ]
Forlani, L [1 ]
机构
[1] Dipartimento Chim Organ A Mangini, I-40136 Bologna, Italy
来源
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2 | 2001年 / 08期
关键词
D O I
10.1039/b009650o
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Spectroscopic and kinetic investigations on the reactions between 4,6-dinitrobenzofuroxan, 4-nitrobenzofuroxan and tertiary and secondary amines (i.e. 1,4-diazabicyclo[2.2.2]octane, quinuclidine, 1,8-diazabicyclo[5.4.0]undec-7-ene and piperidine) indicate the formation of zwitterionic or anionic complexes. The equilibrium between zwitterionic and anionic complexes is discussed (for reaction with piperidine) on the basis of H-1 NMR spectral data, which indicate the presence of anionic complexes arising from the zwitterionic complex by a fast proton departure. The stability and the rate of formation of title complexes are discussed and compared to similar reactions of 1,3,5-trinitrobenzene.
引用
收藏
页码:1408 / 1413
页数:6
相关论文
共 33 条
[11]   An NMR study and ab initio molecular orbital calculation of substituted benzofuroxans and the salt of 4,6-dinitrobenzofuroxan [J].
Cmoch, P ;
Wiench, JW ;
Stefaniak, L ;
Webb, GA .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 1999, 55 (11) :2207-2214
[12]   COMPLEX-FORMATION BETWEEN 1,3,5-TRINITROBENZENE AND 1,8-DIAZABICYCLO-[5,4,0]-UNDEC-7-ENE [J].
COLLINA, G ;
FORLANI, L .
JOURNAL OF PHYSICAL ORGANIC CHEMISTRY, 1988, 1 (06) :351-357
[13]   The reactions of 4-nitrobenzofuroxan with amines in DMSO; kinetic and equilibrium studies [J].
Crampton, MR ;
Delaney, J ;
Rabbitt, LC .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1999, (11) :2473-2480
[14]  
Drost P., 1899, ANN CHEM, V307, P49
[15]  
Exner O., 1972, ADV LINEAR FREE ENER
[16]  
Forlani L, 1999, J PHYS ORG CHEM, V12, P417, DOI 10.1002/(SICI)1099-1395(199906)12:6<417::AID-POC158>3.0.CO
[17]  
2-V
[19]  
FORLANI L, 1986, J CHEM RES-S, P344
[20]  
Forlani L., 1996, CHEM AMINO NITROSO N