Abstract

In this work, the structural and electronic properties of 4-[(E)-[4-(trifloromethyl)-1,3-benzothiazol-2-yl]azo]naphthalen-1-ol (ortho-OH) and 1-[(E)-[4-(trifloromethyl)-1,3-benzothiazol-2-yl]azo]naphthalen-2-ol (para-OH) using density functional theory (DFT) were presented. The calculated vibrational frequencies were compared very well with experimental. The total energy for the isomers A and B were -4277242.55 and -4277216.21 kJ/mol respectively; thus structural relaxation was observed in isomer A which resulted into extra thermodynamic stability over isomer B by 26.34 kJ/mol. ¹³C and ¹H NMR chemical shifts for two isomers were calculated and compared. Electrophilicity index revealed that isomer A would be mote reactive towards nucleophiles more than isomer B.

Key words: 4-[(E)-[4-(trifloromethyl)-1,3-benzothiazol-2-yl]azo]naphthalen-1-ol, 1-[(E)-[4-(trifloromethyl)-1,3-benzothiazol-2-yl]azo]naphthalen-2-ol, electronic properties, density functional theory (DFT).