Microwave assisted solid-state synthesis of functional organotin carboxylates from sterically encumbered 3,5-di-tert-butylsalicylic acid

Murugavel, Ramaswamy; Gogoi, Nayanmoni

doi:10.1016/j.jorganchem.2008.04.001

Cited by 27 publications

(6 citation statements)

References 31 publications

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“…On the contrary, with the dicationic tin(IV) fragment [ n Bu 2 Sn] 2+ , the metal atoms are linked to the salicylate group of dianionic [L meta ] 2– by chelate ring formation with both the phenolate and the carboxylate group (Figure b). There are only a few previous reports on diorganotin complexes derived from salicylate ligands, most of which are bis(tetraorganodistannoxanes) − and diorganotin dicarboxylates with skew-trapezoidal bipyramidal tin coordination geometry. − In complexes with bidentate O,O ′-ligands coordinated to diorganotin moieties, intermolecular association via O→Sn coordination to a dimeric aggregate frequently takes place, giving overall six- or seven-coordinate tin complexes with octahedral or pentagonal-bipyramidal environments (Figure b). , …”

Section: Discussionmentioning

confidence: 99%

Coordination-Driven Self-Assembly of Macrocycles and 1D or 2D Coordination Polymers Using Heteroditopic Pyridyl-Carboxylate Ligands: The Case Study of 5-[(E)-2-(3-Pyridyl)-1-Diazenyl]-2-Hydroxybenzoate in Combination with {R_nSn} (n = 2 and 3)

Baul

Chaurasiya

Duthie

et al. 2019

Crystal Growth & Design

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Pro-ligand 5-[(E)-2-(3-pyridyl)-1-diazenyl]-2hydroxybenzoic acid, H′HL meta , was employed for the synthesis of four organotin(IV) complexes, using suitable tri-and diorganotin (IV) precursors, [nBu 3 Sn(HL meta )] n (1), [Bz 3 Sn(HL meta )] n •C 6 H 5 CH 3 (2), [Ph 3 Sn(HL meta )] 4 •C 6 H 5 CH 3 (3), and {[nBu 2 Sn(L meta )] 2 } n •2nDMSO (4). The coordination behavior of compounds 1−3 in solution was judged from the results of the 119 Sn NMR spectroscopic characterization, while the 119 Sn MAS NMR technique was utilized to probe 4, owing to its low-solubility issue. The solid-state structures of 1−4 were determined from single-crystal X-ray diffraction data. The structural analysis revealed that by changing the Sn-R substituents, the molecular coordination geometries and supramolecular structural motifs in the resulting compounds are widely affected. However, one common feature in the crystal structures of these compounds is a strong tendency for the terminal pyridyl nitrogen to bind with the tin atom of an adjacent complex molecule, which influences the ligand bonding interactions and leads to either macrocycle or polymer formation. In compounds 1−3, the triorganotin moieties are embedded in trigonal− bipyramidal coordination polyhedra arising from the ligand in the monodeprotonated salicylate form, [HL meta ] − , by complexation through the carboxylate group, resulting in 1D coordination polymers with a zigzag-type topology for compounds 1 and 2, and a tetranuclear 44-membered macrocyclic ring structure in the case of 3. The different outcome is a result of the all anti-conformation of the [HL meta ] − ligands in compounds 1 and 2, compared with alternating syn-and anti-conformation of the four ligands in 3, and is without doubt related to the variation of the triorganotin functionality. In compound 4, the tin atoms coordinate to the salicylate group of dianionic [L meta ] 2− by chelate ring formation with both the carboxylate and phenolate groups. The combination of syn-conformation of the ligand and secondary building block formation through 4-membered Sn 2 O 2 rings gives rise to 1D tapes containing 22-membered tetranuclear macrocycles. The case study reported herein showed that heteroditopic pyridyl-carboxylate ligands derived from salicylic acid by diazonium coupling are providing an interesting ligand family for complexation and self-assembly studies with a large number of single main group and transition ions and preformed di-or oligonuclear tectons.

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Section: Discussionmentioning

confidence: 99%

Coordination-Driven Self-Assembly of Macrocycles and 1D or 2D Coordination Polymers Using Heteroditopic Pyridyl-Carboxylate Ligands: The Case Study of 5-[(E)-2-(3-Pyridyl)-1-Diazenyl]-2-Hydroxybenzoate in Combination with {R_nSn} (n = 2 and 3)

Baul

Chaurasiya

Duthie

et al. 2019

Crystal Growth & Design

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“…The organooxotin clusters can be chemically modified by organic ligands with carefully selective spacers or tailed groups . The successful introduction of numerous functional O-donor ligands into organooxotin clusters has produced a wide variety of fascinating organooxotin-cluster-based structural patterns . In this regard, the functional O-donor ligands, such as carboxylic acids, phosphinic acids, phosphonic acids, and arsonate, , have been successively used to mediate the organooxotin clusters.…”

Section: Introductionmentioning

confidence: 99%

Molecular Dumbbell, Sandwich, and Paddle-Wheel Assembled with Methylresorcin[4]arene Cavitands and Organooxotin Clusters

Dong

Shi

Yang

et al. 2015

Crystal Growth & Design

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Assemblies of two methylresorcin[4]arene cavitands with Bu 2 SnO and n-BuSn(O)OH afforded four organooxotin-cluster-based compou nds, namely, [(Bu 2 Sn) 2It is the first time that the methylresorcin[4]arene cavitands were successfully incorporated into the organooxotin clusters. Both 1 and 2 exhibit similar dumbbell-like structures, where the skeletons of methylresorcin[4]arene cavitands stretch in different directions on account of the different configurations of the carboxylate groups of L1 and L2 anions. As a result, the C−H•••π interactions lead to slightly distinct 1D supramolecular architectures of 1 and 2. 3 displays a sandwich-like structure based on one [(BuSn) 12 (μ 3 -O) 14 (μ 2 -OH) 6 ] 2+ macrocation and two L1 anions, where the macrocation is trapped in the dimeric L1 anions through O−H•••O hydrogen-bonding interactions. The sandwiches further stack through π−π interactions to afford a supramolecular dimer. 4 exhibits an unusual giant paddle-wheel motif composed of a typical Sn 6 O 6 drum and six L2 anions. Further, the paddle-wheel motifs are extended by π−π interactions to give a supramolecular layer. Moreover, the luminescent properties of 2 and 4 and the preliminary anticancer activity of 4 were also investigated.

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“…For these reasons, microwave-assisted synthesis has become a rapidly growing field of study, especially for various organic transformations (Ju et al, 2006;Petricci et al, 2006;Schirok, 2006). Synthesis of organotin carboxylates using microwaves has already been reported in the literature (Murugavel and Gogoi, 2008).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and characterization of some new di- and triorganotin(IV) complexes of Schiff base derived from o-vanillin and acetazolamide using microwaves

Kaur

Puri²,

Kapila

et al. 2013

Main Group Metal Chemistry

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Microwave assisted solid-state synthesis of functional organotin carboxylates from sterically encumbered 3,5-di-tert-butylsalicylic acid

Cited by 27 publications

References 31 publications

Coordination-Driven Self-Assembly of Macrocycles and 1D or 2D Coordination Polymers Using Heteroditopic Pyridyl-Carboxylate Ligands: The Case Study of 5-[(E)-2-(3-Pyridyl)-1-Diazenyl]-2-Hydroxybenzoate in Combination with {R_nSn} (n = 2 and 3)

Coordination-Driven Self-Assembly of Macrocycles and 1D or 2D Coordination Polymers Using Heteroditopic Pyridyl-Carboxylate Ligands: The Case Study of 5-[(E)-2-(3-Pyridyl)-1-Diazenyl]-2-Hydroxybenzoate in Combination with {R_nSn} (n = 2 and 3)

Molecular Dumbbell, Sandwich, and Paddle-Wheel Assembled with Methylresorcin[4]arene Cavitands and Organooxotin Clusters

Synthesis and characterization of some new di- and triorganotin(IV) complexes of Schiff base derived from o-vanillin and acetazolamide using microwaves

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Microwave assisted solid-state synthesis of functional organotin carboxylates from sterically encumbered 3,5-di-tert-butylsalicylic acid

Cited by 27 publications

References 31 publications

Coordination-Driven Self-Assembly of Macrocycles and 1D or 2D Coordination Polymers Using Heteroditopic Pyridyl-Carboxylate Ligands: The Case Study of 5-[(E)-2-(3-Pyridyl)-1-Diazenyl]-2-Hydroxybenzoate in Combination with {RnSn} (n = 2 and 3)

Coordination-Driven Self-Assembly of Macrocycles and 1D or 2D Coordination Polymers Using Heteroditopic Pyridyl-Carboxylate Ligands: The Case Study of 5-[(E)-2-(3-Pyridyl)-1-Diazenyl]-2-Hydroxybenzoate in Combination with {RnSn} (n = 2 and 3)

Molecular Dumbbell, Sandwich, and Paddle-Wheel Assembled with Methylresorcin[4]arene Cavitands and Organooxotin Clusters

Synthesis and characterization of some new di- and triorganotin(IV) complexes of Schiff base derived from o-vanillin and acetazolamide using microwaves

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Product

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Coordination-Driven Self-Assembly of Macrocycles and 1D or 2D Coordination Polymers Using Heteroditopic Pyridyl-Carboxylate Ligands: The Case Study of 5-[(E)-2-(3-Pyridyl)-1-Diazenyl]-2-Hydroxybenzoate in Combination with {R_nSn} (n = 2 and 3)

Coordination-Driven Self-Assembly of Macrocycles and 1D or 2D Coordination Polymers Using Heteroditopic Pyridyl-Carboxylate Ligands: The Case Study of 5-[(E)-2-(3-Pyridyl)-1-Diazenyl]-2-Hydroxybenzoate in Combination with {R_nSn} (n = 2 and 3)