Investigation of the role of ortho, meta and para situation of halide functional groups on the electronic structureand aromaticity of phenol molecule

In this study the role of ortho, meta and para situation of different halide functional groups on the electronicstructure and aromaticity of phenol molecule has been investigated. Results indicate that the stability energy of threeisomers of bromophenol are so closed together. About the chlorophenol, the para isomer have lower stability energy,comparing with two other isomers. On the other hand, the stability energy of ortho and para isomers are so closedtogether. In the case of fluorophenol, the para isomer is meaningfully less stable than two other isomers. In all studiedderivatives the O-H bond length in ortho isomers have the most value between three isomers. Simultaneously, the O-Cbond lengths are the shortest. All considered functionalized phenol compounds have the most value of dipole momentin para state. The most value of the dipole moment among all considered molecules is belong to para boromo phenol.Substitution of Br and F in ortho situation causes to maximize the aromaticity of benzene ring. On the other hand,substitution of Cl group in para situation causes to maximize the aromaticity of chlorophenol. The most value of theNICS (1)ZZ among all considered molecules is belong to ortho fluoro phenol.

کلیدواژه ها:

aromaticity ، NICS ، substitution effect