Bistripodand Amide Host for Compartmental Recognition of Multiple Oxyanions

Arunachalam, M.; Ghosh, Pradyut

doi:10.1021/ol9026649

Cited by 48 publications

(25 citation statements)

References 49 publications

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“…Fig. 51,52 In all these six complexes we observe that the amide protons are directed towards cavity of the tripodal cle that bind AcO À . complexes 3-5 in solid state where a 1 : 2, host : acetate recognition is clearly evident.…”

Section: Introductionmentioning

confidence: 82%

“…51,52,57 Hexakis(aminomethyl)benzene (0.303 g, 1.2 mmol) and 1 mL triethylamine were dissolved in 100 mL dry tetrahydrofuran and stirred at 0 C for 20 minutes under N 2 atmosphere. 51,52,57 Hexakis(aminomethyl)benzene (0.303 g, 1.2 mmol) and 1 mL triethylamine were dissolved in 100 mL dry tetrahydrofuran and stirred at 0 C for 20 minutes under N 2 atmosphere.…”

Section: Methodsmentioning

confidence: 99%

“…51,52,57 Single crystal X-ray crystallographic details 51,52,57 Single crystal X-ray crystallographic details…”

Section: Details Of Complexes 6-12mentioning

confidence: 99%

“…Chloride is an integral part of chloride channels which is responsible for transport in human body. 51,52,57 Herein we report a series of neutral hexa-amide receptors that have shown structural diversities upon guest binding depending on basicity of the guests and substitutions on the receptor backbone. For example, carboxylates have specic biochemical behaviors and act as crucial components in metabolic pathways.…”

Section: Introductionmentioning

confidence: 99%

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Arene platform based hexa-amide receptors for anion recognition: single crystal X-ray structural and thermodynamic studies

et al. 2015

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Five newly synthesized hexa-amide receptors (L1-L5) and previously reported three such receptors (L6-L8) have been explored to investigate binding propensity of anions of various shapes and sizes. Single crystal X-ray structures of five new anion complexes of receptors (L1-L5), complexes (1-5) and previously reported seven such complexes of (L6-L8), complexes (6-12) fall under four categories of conformations such as aaabbb (A), ababab (B), aabaab (C) and aaaaaa (D) depending upon basicity of the anions as well as substituents on the receptor backbones. Moderately basic guest; chloride exhibits two different conformers with A and B patterns with L1 (R ¼ -oNO 2 C 6 H 4 , complex 1) and L4 (R ¼ -pFC 6 H 4 , complex 2) respectively in 1 : 2 (host : guest) stoichiometry. On the other hand, strongly basic acetatecomplexes 3-8 respectively, exhibit a chair like conformer (A) with 1 : 2 (host : guest) stoichiometry. Our previous studies showed recognition of nitrate-water cluster (9) by L6 and nitrate (10) by L8 with (B) and (C) conformations respectively and an unusual conformation (D) was isolated in cases of L7 and L8 with hydrated fluoride clusters [(F) 4 (H 2 O) 10 ] 4À (11) and [(F) 4 (H 2 O) 6 ] 4À (12) respectively. Solution state ITC and NMR studies have also shown 1 : 2 stoichiometry of host : guest binding of acetate and fluoride with L1-L8. Results and discussionThe hexa-amide receptors L1-L5 are synthesized with various electron withdrawing groups like -NO 2 (L1, L2 and L7) -F (L4, L6), -CF 3 (L3 and L8) which are attached in different positions to assess their role in anion complexation via electronic and steric effects (Scheme 1). 51,52,57 Crystallization with various anions resulted acetate, nitrate, chloride and uoride guest bound structures with this series of receptors. Crystals suitable for single crystal X-ray diffraction studies are obtained for

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Section: Introductionmentioning

confidence: 82%

Section: Methodsmentioning

confidence: 99%

“…51,52,57 Single crystal X-ray crystallographic details 51,52,57 Single crystal X-ray crystallographic details…”

Section: Details Of Complexes 6-12mentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Arene platform based hexa-amide receptors for anion recognition: single crystal X-ray structural and thermodynamic studies

et al. 2015

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“…Because of the distinctive features of synthetic tripodal receptor system, their design and development is a very active field of study in the supramolecular chemistry. 6,7,18,19 An amide functional group, which exists in the structure of many synthetic materials, is very important in the organic chemistry and biochemistry. Therefore, the synthesis of compounds containing amide functionality is of interest in synthetic chemistry.…”

Section: Introductionmentioning

confidence: 99%

Microwave-assisted synthesis of novel amide based chiral tripodal receptors for recognition of cation and anion sensors

Azizoglu¹,

Kaplan²,

Öztürk³

et al. 2016

Arkivoc

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Five novel amide based chiral tripodal receptors were synthesized under microwave irradiation by reacting nitrilotriacetic acid with chiral amino alcohols in a solvent-free medium with high yields (≥ 90%). The recognition affinities of these tripodal receptors were investigated towards anions and chiral organic ammonium cations using 1 H NMR titration method. The results show that receptor 1 displays more affinity against anions compared with other receptors and the tripodal receptor 4 demonstrated a significant enantiomeric selectivity towards the (R)-naphthylethylammonium perchlorate (ERF 54%).

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Aromatische Ringe in chemischer und biologischer Erkennung: Energien und Strukturen

2011

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Dieser Aufsatz beschreibt Phänomene der molekularen Erkennung von aromatischen Ringen in chemischen und biologischen Systemen in einem multidimensionalen Ansatz. Neue Ergebnisse aus der Wirt‐Gast‐Chemie, biologischen Affinitätsassays und Biostrukturanalysen, Datenbanksuchen in der Cambridge Structural Database (CSD) und der Protein Data Bank (PDB) und hochentwickelten Rechnungen, die seit dem Erscheinen eines früheren Aufsatzes in 2003 veröffentlicht wurden, sind hier zusammengefasst. Die Themen Aren‐Aren‐, Perfluoraren‐Aren‐, Schwefel‐Aren‐, Kation‐π‐ und Anion‐π‐Wechselwirkungen sowie Wasserstoffbrücken zu aromatischen Systemen werden behandelt. Das gewonnene Wissen kommt besonders der strukturbasierten Hit‐zur‐Leitstruktur‐Entwicklung und der Leitstrukturoptimierung sowohl in der pharmazeutischen als auch in der Pflanzenschutzindustrie zugute. Zudem erleichtert es die Entwicklung neuer Materialien und supramolekularer Systeme und soll zu weiteren Anwendungen von Wechselwirkungen mit aromatischen Ringen zur Kontrolle des stereochemischen Verlaufs chemischer Umsetzungen inspirieren.

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Bistripodand Amide Host for Compartmental Recognition of Multiple Oxyanions

Cited by 48 publications

References 49 publications

Arene platform based hexa-amide receptors for anion recognition: single crystal X-ray structural and thermodynamic studies

Arene platform based hexa-amide receptors for anion recognition: single crystal X-ray structural and thermodynamic studies

Microwave-assisted synthesis of novel amide based chiral tripodal receptors for recognition of cation and anion sensors

Aromatische Ringe in chemischer und biologischer Erkennung: Energien und Strukturen

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