Theoretical study of the ortho, meta and para substitution of different electron withdrawing functional groups in phenol derivatives
کد مقاله : 1007-PHYSCHEM20
لیلا نیکوپور، مریم سوری *
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چکیده مقاله:
Even though aromaticity cannot be directly probed, it has, nevertheless, traditionally been associated with at least three types of measurable molecular effects: structural, energetic and magnetic. In this study the role of ortho, meta and para situation of different electron withdrawing functional groups on the electronic structure and aromaticity of phenol molecule has been investigated. Geometry of considered phenol derivatives have been optimized in B3LYP/6-311++G** level of theory. Results show that, the stability of ortho isomers of various substituted phenols are more than meta and para isomers. In addition, ortho isomers have more acidic characteristic, comparing with meta and para substituted derivatives of phenol. The natural charges confirm this statement. On the other hand, when functional groups sit on meta position, NICS (1)ZZ values are close together, no matter what is the functional group. But different functional groups cause to different NICS (1)ZZ for benzene ring, when they sit on the ortho position. In ortho position, COCH3 substituted phenol have the most aromaticity. CN and CHO functionalized phenol are in the next orders.
کلیدواژه ها:
substitution effect, electron withdrawing groups, phenol, NICS
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