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Crystal Structure of 2-((E)-((Z)-3-(((4-hydroxyphenyl)amino)methylene)-4-oxocyclohexa-1,5-dien-1-yl)diazenyl)benzoic Acid and Synthesis, Spectroscopy, and DFT Study of Its Dibutyltin(IV) Complex
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Crystal Structure of 2-((E)-((Z)-3-(((4-hydroxyphenyl)amino)methylene)-4-oxocyclohexa-1,5-dien-1-yl)diazenyl)benzoic Acid and Synthesis, Spectroscopy, and DFT Study of Its Dibutyltin(IV) Complex
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Crystal Structure of 2-((E)-((Z)-3-(((4-hydroxyphenyl)amino)methylene)-4-oxocyclohexa-1,5-dien-1-yl)diazenyl)benzoic Acid and Synthesis, Spectroscopy, and DFT Study of Its Dibutyltin(IV) Complex
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Journal Article
Crystal Structure of 2-((E)-((Z)-3-(((4-hydroxyphenyl)amino)methylene)-4-oxocyclohexa-1,5-dien-1-yl)diazenyl)benzoic Acid and Synthesis, Spectroscopy, and DFT Study of Its Dibutyltin(IV) Complex
2024
Overview
The structure of the 2-((
E
)-((
Z
)-3-(((4-hydroxyphenyl)amino)methylene)-4-oxocyclohexa-1,5-dien-1-yl)diazenyl)benzoic acid (H
3
L) was confirmed by single crystal X-ray diffraction and Hirshfeld surface analysis was used further to quantify the intermolecular interactions. It crystallized in monoclinic space group
P
2
1
/c. The observed bond distances evidence that the structure exists predominately in azo-enamine tautomeric form in the solid state. A novel dibutyltin(IV) complex, [(Bu
2
SnHL)
2
] (
1
) was synthesized from H
3
L. The complex was then characterized by studying different techniques including elemental analysis, FT-IR, and NMR (
1
H,
13
C, and
119
Sn) spectroscopy. In solution state, the molar mass of the compound was confirmed by Mass spectrometry. Spectroscopy study guides to predict the structure of the complex which is supposed to be a cyclic dimer [(Bu
2
SnHL)
2
] and Sn(IV) adopts a six-coordinated geometry. However, in solution Sn(IV) adopts four coordinated distorted tetrahedral geometry which was supported by
119
Sn NMR spectroscopy (δ
Sn(119)
, 126.34 ppm) and EI-MS results of the complex ion ([C
28
H
32
N
3
O
4
Sn]
+
,m/z 593.1). Further, the structures in solid and solution state were supported by developing their optimized structures and IR data from the DFT calculation.
Graphical Abstract
The crystal structure of the ligand is in azo-enamine tautomeric form and in accordance with DFT study, its dibutyltin(IV) complex is a cyclic dimer, (Bu
2
SnHL)
2
, which becomes monomer in solution.
Publisher
Springer US,Springer Nature B.V
