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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


Basu Baul, T S; Paul, A; Linden, A (2012). 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. Journal of Organometallic Chemistry, 696(26):4229-4235.

Abstract

Three triorganotin(IV) complexes of composition R3SnLH (R = Me, Bu and Ph and LH = 2-[(E)-2-(4-hydroxy-3,5-dimethylphenyl)-1-diazenyl]benzoate) have been synthesized and characterized by 1H-,13C-, 119Sn- NMR, and IR spectroscopic techniques in combination with elemental analysis. The crystal structures of the carboxylate ligand HO2CC6H4{N=N(C6H2-4-OH-3,5-(CH3)2)}-o in its neutral form and three triorganotin(IV) complexes, viz., polymeric (R3Sn[O2CC6H4{N-N(H)(C6H2-4-O-3,5-(CH3)2)}-o])n (R = Me (1) and Bu (2)) and monomeric Ph3Sn[O2CC6H4{N-N(H)(C6H2-4-O-3,5-(CH3)2)}-o] (3) complexes are reported. The polymeric complexes 1 and 2 exist as extended chains in which the LH-bridged Sn-atoms adopt a trans-R3SnO2 trigonal bipyramidal configuration with R groups in the equatorial positions and the axial sites occupied by an oxygen atom from the carboxylate ligand and the phenoxide O atom of the next carboxylate ligand. The Sn atom in complex 3 has a distorted tetrahedral geometry. In all three complexes, the carboxylate ligand is in the zwitterionic form 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.

Three triorganotin(IV) complexes of composition R3SnLH (R = Me, Bu and Ph and LH = 2-[(E)-2-(4-hydroxy-3,5-dimethylphenyl)-1-diazenyl]benzoate) have been synthesized and characterized by 1H-,13C-, 119Sn- NMR, and IR spectroscopic techniques in combination with elemental analysis. The crystal structures of the carboxylate ligand HO2CC6H4{N=N(C6H2-4-OH-3,5-(CH3)2)}-o in its neutral form and three triorganotin(IV) complexes, viz., polymeric (R3Sn[O2CC6H4{N-N(H)(C6H2-4-O-3,5-(CH3)2)}-o])n (R = Me (1) and Bu (2)) and monomeric Ph3Sn[O2CC6H4{N-N(H)(C6H2-4-O-3,5-(CH3)2)}-o] (3) complexes are reported. The polymeric complexes 1 and 2 exist as extended chains in which the LH-bridged Sn-atoms adopt a trans-R3SnO2 trigonal bipyramidal configuration with R groups in the equatorial positions and the axial sites occupied by an oxygen atom from the carboxylate ligand and the phenoxide O atom of the next carboxylate ligand. The Sn atom in complex 3 has a distorted tetrahedral geometry. In all three complexes, the carboxylate ligand is in the zwitterionic form 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.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Uncontrolled Keywords:Triorganotin Carboxylate 2-[(E)-2-(4-Hydroxy-3,5-dimethylphenyl)- 1-diazenyl]benzoic acid NMR Crystal structure
Language:English
Date:2012
Deposited On:12 Dec 2011 11:35
Last Modified:05 Apr 2016 15:08
Publisher:Elsevier
ISSN:0022-328X
Funders:Department of Science & Technology, New Delhi, India (Grant No. SR/S1/IC-03/2005, TSBB), Council of Scientific and Industrial Research, New Delhi, India (Grant No. 09/347/(0197)/2011/EMR I, Senior Research Fellowship, AP), the University Grants Commission, New Delhi, India through SAP-DSA, Phase III, Indo-Swiss Joint Research Programme, Joint Utilisation of Advanced Facilities (Grant No. JUAF 11, TSBB, AL)
Publisher DOI:https://doi.org/10.1016/j.jorganchem.2011.09.018
Permanent URL: https://doi.org/10.5167/uzh-51714

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