Investigation of charge transfer complexes formed between 3,3′-dimethylbenzidine (o-toluidine) donor and DDQ, p-chloranil and TCNQ as π-acceptors

• 来源期刊: 科学通报(英文版)
• 学科: 化学
• 年，卷（期）: 2011,（19）
• 页码范围: 1993-2000
• 页数: 8页
• 分类号: O621.3
• 语种: 中文

摘要

Charge-transfer (CT) complex of o-toluidine (o-tol) with the π-acceptor tetrachloro-p-benzoquinone (p-chloranil; CHL) has been synthesized and characterized, along with the products of the elimination reaction of o-toluidine (o-tol) with 2,3-dichloro-5,6dicyano-p-benzoquinone (DDQ) and 7,7,8,8-tetracyanoquinodimethane (TCNQ). Their properties and structures have been investigated using electronic absorption and IR spectroscopy as well as elemental analyses of the isolated compounds. The o-tol/p-CHL CT complex is shown to consist of a CHL radical anion and o-tol + radical cation. The formations of all three compounds result in the appearance of new UV-Vis spectral bands that peaked in intensity at a stoichiometric ratio of 1 : 1. 1 H-NMR and mass spectra were used to confirm the formation of the o-tol/DDQ and o-tol/TCNQ products. The new 7,8-dicyano-7′,8′-o-toluidilequinodimethane and 2,3-dichloro-5-cyano-6-o-toluidil-p-benzoquinone products resulted from the rapid reaction of o-tol with TCNQ and DDQ, respectively. Thermogravimetric studies showed that the CT-complex decomposes in three steps whereas the new compounds decompose in a single step. Thermodynamic parameters were computed from the thermal decomposition data.