Substituent effect on the stability and electronic properties of naphthalene and azulene: A computational investigation

Subject Areas : Iranian Journal of Organic Chemistry

Reza  Jafari ¹ ()
Reza  Ghiasi ² ()
Bita  Mohtat ³ ()

Received: 2023-02-26 Accepted : 2023-02-26 Published : 2022-11-01

Keywords: Naphthalene, Azulene, Substituent effect, Bicyclobutane mechanism, Time-dependent Density functional theory (TD-DFT), Harmonic oscillator model of aromaticity (HOMA),

Abstract :

In this research, substituent effect on the stability and electronic properties of naphthalene and azulene studied. Hydrogen atoms of the studied molecules were replaced with methyl, fluoride and chloride substituents. Calculations were done at the M062X/6-311G(d,p) level of theory. Bicyclobutane mechanism was considered for the rearrangement of azulene to naphthalene and substituent effect on the activation energy values were illustrated with the density functional calculations. Harmonic oscillator model of aromaticity (HOMA) parameters were used to illustration of aromoaticity in the studied molecules. Also, frontier orbital analysis in the azulenes and naphthalenes were reported.