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

作　　者：REFAT Moamen S El-METWALLY Nashwa M 

机构地区：[1]Department of Chemistry, Faculty of Science, Port Said University [2]Department of Chemistry, Faculty of Science, Taif University [3]Department of Chemistry, Faculty of Education, King Khaled University

出　　处：《Chinese Science Bulletin》2011年第19期1993-2000,共8页

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.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-5,6- dicyano-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 ： 1.1H-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-toluidilequino- dimethane 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.

关 键 词：电荷转移复合物 四氯对苯醌 TCNQ DDQ 甲基苯胺 受体 二甲基 电子吸收光谱 

分 类 号：O621.3[理学—有机化学]