TY - JOUR

T1 - 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

AU - Debnath, Pratima

AU - Majumder, Chinmoy

AU - Bhattacharya, Arnab

AU - Debnath, Paresh

AU - Roy, Subhadip

AU - Novikov, Alexander S.

AU - Roy, Manojit

AU - Misra, Tarun Kumar

PY - 2023/11/23

Y1 - 2023/11/23

N2 - The structure of the 2-((E)-((Z)-3-(((4-hydroxyphenyl)amino)methylene)-4-oxocyclohexa-1,5-dien-1-yl)diazenyl)benzoic acid (H3L) 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 P21/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, [(Bu2SnHL)2] (1) was synthesized from H3L. The complex was then characterized by studying different techniques including elemental analysis, FT-IR, and NMR (1H, 13C, and 119Sn) 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 [(Bu2SnHL)2] and Sn(IV) adopts a six-coordinated geometry. However, in solution Sn(IV) adopts four coordinated distorted tetrahedral geometry which was supported by 119Sn NMR spectroscopy (δSn(119), 126.34 ppm) and EI-MS results of the complex ion ([C28H32N3O4Sn]+,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, (Bu2SnHL)2, which becomes monomer in solution. [Figure not available: see fulltext.].

AB - The structure of the 2-((E)-((Z)-3-(((4-hydroxyphenyl)amino)methylene)-4-oxocyclohexa-1,5-dien-1-yl)diazenyl)benzoic acid (H3L) 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 P21/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, [(Bu2SnHL)2] (1) was synthesized from H3L. The complex was then characterized by studying different techniques including elemental analysis, FT-IR, and NMR (1H, 13C, and 119Sn) 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 [(Bu2SnHL)2] and Sn(IV) adopts a six-coordinated geometry. However, in solution Sn(IV) adopts four coordinated distorted tetrahedral geometry which was supported by 119Sn NMR spectroscopy (δSn(119), 126.34 ppm) and EI-MS results of the complex ion ([C28H32N3O4Sn]+,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, (Bu2SnHL)2, which becomes monomer in solution. [Figure not available: see fulltext.].

KW - DFT

KW - Dibutyltin(IV) complex

KW - Hirshfeld surface analysis

KW - Mass spectrometry

KW - Spectroscopy

KW - X-ray structure

UR - https://www.mendeley.com/catalogue/e906ffd7-9029-3df0-8a0c-2b8e87cd8813/

U2 - 10.1007/s10870-023-00996-y

DO - 10.1007/s10870-023-00996-y

M3 - Article

JO - Journal of Chemical Crystallography

JF - Journal of Chemical Crystallography

SN - 1074-1542

ER -