Chlorination of anisole, toluene and nitrobenzene using trichloroisocyanuric acid (tica): computational issues on reactivity and regioselectivity

Química Nova

Lima Junior, Cláudio G.¹  Universidade Federal da Paraíba, João Pessoa, Brasil¹  Vasconcellos, Mário L. A. A.¹ 

关键词: undergraduate organic chemistry teaching;    chlorination of the aromatic compounds;    computer education.;   

DOI  :  10.1590/S0100-40422009000100041

学科分类：化学（综合）

来源: Sociedade Brasileira de Quimica

【 摘 要 】

We present in this educational article a theoretical analysis based on DFT/B3LYP 6-311++G (d,p) and ab initio MP2/6-311++G(d,p) computational calculation about the reactivity and the regioselectivity on the chlorination reaction of anisole, toluene and nitrobenzene, using trichloroisocyanuric acid (TICA) as donor of Cl+. The H.O.M.O. / L.U.M.O. energy and N.B.O. atomic charges of various aromatic systems were calculated in ab initio level. The energies of the reagents and intermediaries were calculated using D.F.T.. These results have been presented as a quantitative example for the SEA mechanism, in the undergraduate organic chemistry disciplines.

【 授权许可】

Unknown