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2-Propylamino-5-[4-(2-hydroxy-3,5-dichlorobenzylideneamino) phenyl]-1,3,4-thiadiazole, formulated as C
18
H
16
Cl
2
N
4
OS (
I
), was synthesized. The crystal and molecular structure of (
I
) have been determined by
1
H-NMR, IR, and X-ray single crystal diffraction. The compound (
I
) crystallizes in the monoclinic, space group
P
2(1)/
c
with unit cell parameters
a
= 9.0576(2) Å,
b
= 24.3382(8) Å,
c
= 9.0585(2) Å,
M
r
= 407.31,
V
= 1851.13(9) Å
3
,
Z
= 4,
R
1
= 0.036, and
wR
2
= 0.096. Molecular geometry from X-ray experiment of (
I
) in the ground state has been compared using the density functional method (B3LYP) with 6-31G(d) basis set. To determine conformational flexibility, molecular energy profile of (
I
) was obtained by semi-empirical (PM3) calculations with respect to selected degree of torsional freedom, which was varied from −180° to +180° in steps of 10°. The results are indicative that the Schiff base, which contains a thiadiazole ring, prefers to be in E-configuration. In addition, molecular electrostatic potential, frontier molecular orbitals, and natural bond orbitals analysis were performed by the B3LYP/6-31G(d) method.