title: Theoretical study on the regioselectivity of electrophilic aromatic substitution reactions of azulene.
abstract: In this study electrophilic affinities were calculated at all reactive positions of azulene in electrophilic aromatic substitutions. Structures of cationic intermediates and products were optimized at HF/6-31+G* and B3LYP/6-31+G** levels of theory, and single point calculations were carried out at MP2/6-31+G**//B3LYP/6-31+G** for total energy. NICS calculations, activation energies and relative stabilities (deltaE) were used to predict the most reactive site in azulene. Results indicated that position 1 is the most reactive site for electrophilic aromatic reactions in terms of kinetic considerations, while the isomers with substituents at position 2 are predominantly thermodynamic products.
authors.affiliation: Department of Chemistry, Islamic Azad University, Central Tehran Branch, 146786831 Tehran, Iran. zabarjad_sh@yahoo.com
authors.forename: Nader Zabarjad
authors.initials: NZ
authors.lastname: Shiraz
authors.forename: Elaheh Sadat
authors.initials: ES
authors.lastname: Sharifzadeh
authors.forename: Neda
authors.initials: N
authors.lastname: Koosha