Synthesis, characterization and crystal structures of 2-[(E)-2-(4-hydroxy-3,5-dimethylphenyl)-1-diazenyl]benzoic acid and its polymeric and monomeric triorganotin(IV) complexes

Abstract

with the phenolic proton moved to the nearby azo nitrogen atom, in contrast to the free carboxylic acid ligand which is in the azo form.

Synthesis and Structural Facets of Dialkyltin(IV) Complexes Constructed from 2‐(2‐(3, 5‐Dimethyl‐4‐oxocyclohexa‐2, 5‐dien‐1‐ylidene)hydrazinyl)benzoate

“…The ligand was synthesized by diazotization of 2‐aminobenzoic acid followed by coupling with 2, 6‐dimethylphenol 8. The analytical and spectroscopic data agree with the reported data.…”

“…The pattern of alternating shorter and longer localized bond lengths from the NH group right through to the phenoxide O atom (Table 2) clearly indicates that the ligand adopts the quinoid form and not the zwitterionic form. The quinoid form in tin(IV) complexes with related ligands has been noted previously 8. The ligands are disposed in distorted pentagonal bipyramidal coordination about each tin atom.…”

“…The aim was to see the influence of the azo group nitrogen atoms by docking studies with some key enzymes such as ribonucleotide reductase, thymidylate synthase, thymidylate phosphorylase, and topoisomerase II that take part in the synthesis of raw materials for DNA and its replication. In the same perspective, recently, the crystal structure of 2‐[( E )‐2‐(4‐hydroxy‐3, 5‐dimethylphenyl)‐1‐diazenyl]benzoic acid (HO 2 CC 6 H 4 {N=N(C 6 H 2 ‐4‐OH‐3, 5‐(CH 3 ) 2 )}‐ o ; LHH′) was determined 8. The molecule of LHH′ is approximately planar with just small twists about the central C–N bonds linking the two phenyl rings, as indicated by the torsion angles N(2)–N(1)–C(7)–C(6) = –12.14(12)° and N(1)–N(2)–C(8)–C(9) = 3.63(13)°.…”

“…The molecule of LHH′ is approximately planar with just small twists about the central C–N bonds linking the two phenyl rings, as indicated by the torsion angles N(2)–N(1)–C(7)–C(6) = –12.14(12)° and N(1)–N(2)–C(8)–C(9) = 3.63(13)°. Three triorganotin(IV) complexes of LHH′, viz., polymeric ( R 3 SnLH) n ( R = Me and n Bu: type I ) and monomeric Ph 3 SnLH (type II ) complexes (see Scheme ) were also reported 8. The polymeric complexes of type I exist as extended chains, in which the LH‐bridged Sn atoms adopt a trans ‐ R 3 SnO 2 trigonal bipyramidal coordination with R groups in the equatorial positions and the axial sites occupied by an oxygen atom from the carboxylate ligand and the phenoxide oxygen atom of the next carboxylate ligand.…”

Structural Diversity in Organotin(IV) Carboxylates: A Study of X-Ray Crystallography

“…A number of studies have been done on organotin(IV) carboxylates by various spectroscopic studies and the molecular structure of these complexes have described by x-ray crystallography 11,12 . Organotin(IV) carboxylates have been known due to its notable and vast structural diversity 8,9,[13][14][15][16] . Interesting tin chemistry has been observed in organotin(IV) carboxylate with different coordination sphere at tin atom.…”