Synthesis, Analytical and Theoretical Studies of (Z)-4-amino-3-hydroxy-2-((4-(N-(5-methylisoxazol-3-yl)Sulfamoyl)Phenyl)Diazenyl)Naphthalene-1-Sulfonic Acid

Abstract

New azodye that characterize (Z)-4-amino-3-hydroxy-2-((4-(N-(5-methylisoxazol-3-yl) sulfamoyl) phenyl)diazenyl)naphthalene-1-sulfonic acid (1) was synthesized. The azodye has been characterized by IR, visible spectra and elemental (CHN) analysis. The results of visible spectra which recorded in the range (360-6540) nm were showed that the maximum wave length (λmax) of azodye was 500 nm. Analytical studies carried on the dye, the results of the solvent effect were showed high solubility in ethanol and water. But, the results of the pH effect in a range of buffer solution were gave three isopestic points. The ionization constant (pKa) and protonation constant (pKb) were calculated by using the half height method. The results were showed that the pKp1 and pKp2 of each nitrogen atom and pKa of OH-group were equal to 2.5, 4.5 and 8.5 respectively. Theoretical studies also carried on azodye (1). The actual and optimal bonds length of -N=N- was equal to 1.248 in each. Though, internal coordinate mechanics (ICM) of (1) was showed that the angle type in most of atoms was dihedral. But, the R and S configuration were observed in other atoms in the structure of azodye. The results also indicated that the torsion angles (ψ) of (1) were variable. High close contacts of atoms were observed in the structure of azodye. The molecular mechanics (MM2) properties was intended for (1), the results showed that the stretch, bend, stretch-bend, torsion, non-1,4 VDW, 1,4 VDW and the total energy were equal to 61.0809, 627.0240, -1.6517, 179.0634, 4686.8146, 33.0379 and 5585.3692 kcal/mol respectively. High VDW interactions of this molecule was observed, due to the results of dipole/dipole were not computed. Thus, the result of MM2 minimization for azodye (1) was showed high VDW interactions of this molecule higher than before the minimization, due to the result of dipole/dipole was also not computed. The high steric energy (1235.782) was affecting the results of minimization. However, the results of the molecular mechanics force field (MMFF94) energy and gradient for azodye (1) were showed that the total energy and RMS gradient were equal to 26223.422 kcal/ mol and 9113.745 respectively. Further, the results of MMFF94 minimization and MMFF94 minimization/sampling of azodye (1) were showed that the minimization was attended successfully using this method.

Keywords: Internal coordinate, Molecular mechanics, Azodyes