1,2-bis(1-aryl-3-alkyltriazen-3-yl)ethanes and related compounds

被引:28
作者
Hooper, DL
Pottie, IR
Vacheresse, M
Vaughan, K [1 ]
机构
[1] St Marys Univ, Dept Chem, Halifax, NS B3H 3C3, Canada
[2] Dalhousie Univ, Dept Chem, Halifax, NS B3H 4J3, Canada
来源
CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE | 1998年 / 76卷 / 01期
关键词
triazene; bistriazene; diazonium; ethylenediamine; molecular dynamics; NMR;
D O I
10.1139/cjc-76-1-125
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of novel bistriazenes, the 1,2-bis(1-aryl-3-methyltriazen-3-yl)ethanes, Ar-N=N-NMe-CH2CH2-NMe-N=N-Ar, have been synthesized by diazonium coupling with N,N'-dimethylethylenediamine. These bistriazenes are stable crystalline compounds and have been unequivocally characterized by IR and NMR spectroscopy (H-1 and C-13), and elemental analysis. The structures of two compounds in the series have been confirmed by X-ray crystallography. The H-1 NMR spectra show significant line broadening of the N-methyl resonances arising from the restricted rotation around the N2-N3 bond of the triazene units. The presence of strongly electron-withdrawing groups on the aryl ring restricts the rotation to the point where the N-methyl signals of the rotamers are distinct even at room temperature; four resonances of the N-methyl signal are clearly evident and these call be assigned to the anti-anti, syn-syn, and syn-anti conformations of the bistriazene. Diazonium coupling with N,N-diethylethylenediamine affords the N,N'-diethyl homologues of the bistriazenes, which have been similarly characterized. As model compounds to assist in spectroscopic analysis, a series of related triazenes, the 1-(1-aryl-3-methyltriazen-3-yl)N,N-dimethyl-2-ethanamines, were prepared by diazonium coupling with N,N,N'-trimethylethylenediamine. These dialkyltriazenes exist mainly as oils, but characterization was achieved by IR, H-1 NMR, and C-13 NMR spectroscopy, also showing the presence of two rotamers in solution when strongly electron-withdrawing substituents are bonded to the aryl moiety.
引用
收藏
页码:125 / 135
页数:11
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