1-[2-(2,6-Diisopropylanilino)-1-naphthyl]isoquinoline

Howard, Ruth H.; Theobald, Nicola; Bochmann, Manfred; Wright, Joseph A.

doi:10.1107/s0108270110018433

Cited by 4 publications

(5 citation statements)

References 14 publications

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“…Hydrogen bonds for ligands H are comparable to the Zn-O bond distances reported in literature 32. Similarly, the Zn-N1 = 2.205(5) and Zn-N2 = 2.094(8) distances are almost comparable to the reported Zn-N bond distances in related coordination complex 32.…”

supporting

confidence: 85%

Synthesis, characterization and phosphotriesterase mimetic activity of some Zn(II) and Cu(II) complexes

et al. 2012

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We report here the synthesis and characterization of a few phenolate-based ligands bearing tertamino substituent and their Zn(II) and Cu(II) metal complexes. Three mono/binuclear Zn(II) and Cu(II) complexes [Zn(L1)(H 2 O)].CH 3 OH.H 2 O (1) (H 2 L1 = 6,6-(((2-dimethylamino)ethylazanediyl)bis(methylene))bis(2, 4-dimethylphenol), [Zn 2 (L2) 2 ] (2) (H 2 L2 = 2,2-(((2-dimethylamino)ethyl)azanediyl)bis(methylene)bis(4methylphenol) and [Cu 2 (L3) 2 .CH 2 Cl 2 ] (3) (H 2 L3 = (6,6-(((2-(diethylamino)ethyl)azanediyl)bis(methylene)) bis(methylene))bis(2,4-dimethylphenol) were synthesized by using three symmetrical tetradendate ligands containing N 2 O 2 donor sites. These complexes are characterized by a variety of techniques including; elemental analysis, mass spectrometry, 1 H, 13 C NMR spectroscopic and single crystal X-ray analysis. The new complexes have been tested for the phosphotriesterase (PTE) activity with the help of 31 P NMR spectroscopy. The 31 P NMR studies show that mononuclear complex [Zn(L1)(H 2 O)].CH 3 OH.H 2 O (1) can hydrolyse the phosphotriester i.e., p-nitrophenyl diphenylphosphate (PNPDPP), more efficiently than the binuclear complexes [Zn 2 (L2) 2 ] (2) and [Cu 2 (L3) 2 .CH 2 Cl 2 ] (3). The mononuclear Zn(II) complex (1) having one coordinated water molecule exhibits significant PTE activity which may be due to the generation of a Zn(II)-bound hydroxide ion during the hydrolysis reactions in CHES buffer at pH 9.0.

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confidence: 85%

Synthesis, characterization and phosphotriesterase mimetic activity of some Zn(II) and Cu(II) complexes

et al. 2012

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“…This highlights the possibility of utilizing conglomerate crystallization as a new chiral pool to provide chemists with sources of chiral information for asymmetric catalysis. Within this list are C 2 symmetrical pyrimidine (OBIPAR 122 ), phosphine (LUSZOO 123 ), and imidazole (ROJPOW 124 ) ligands, an atropisomeric quinoline (TUWFAT 125 ), an α-methylpyridine (DOBWUN 126 ), and a chiral salen ligand (TUNMOF 127 ). Potential types of organocatalysts such as the C 2 symmetrical diol (NULZEA 128 ), a PTC (phase transfer catalyst) crown ether (NOCNIC 129 ), a chiral phosphoric acid (CUVGAB 130 ), chiral ureas (RIPBUN, 131 AZUDAB 132 ), benzotetramisole (YAMBAS 133 ), amino-alcohol (HARFEN 134 ), and imidazole (PURJUJ 135 ) may also find use in asymmetric synthesis.…”

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

“…Potential ligands and organocatalysts from conglomerate crystals. The following crystal structures, labeled by their CSD Refcode, were identified as conglomerates: OBIPAR, 123 LUZOO, 124 PURJUJ, 136 NULZEA, 129 KAQMEV, 168 DOBWUN, 127 ROJPOW, 125 TUWFAT, 126 HARFEN, 135 YAMBAS, 134 CUVGAB, 131 GADTIR, 169 NOCNIC, 130 By tracking materials which undergo this type of crystallization, the possibility of exploiting a powerful mode of chiral amplification can be achieved, whereby a substrate is able to bias its own enantioenrichment. The exciting synthetic potential of conglomerate crystallization has been demonstrated in the case of the natural product Narwedine.…”

Section: Potential Applications Of Conglomerate Crystallization Behaviormentioning

confidence: 99%

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Identifying a Hidden Conglomerate Chiral Pool in the CSD

Walsh

Barclay

Begg

et al. 2022

JACS Au

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Conglomerate crystallization is the spontaneous generation of individually enantioenriched crystals from a nonenantioenriched material. This behavior is responsible for spontaneous resolution and the discovery of molecular chirality by Pasteur. The phenomenon of conglomerate crystallization of chiral organic molecules has been left largely undocumented, with no actively curated list available in the literature. While other crystallographic behaviors can be interrogated by automated searching, conglomerate crystallizations are not identified within the Cambridge Structural Database (CSD) and are therefore not accessible by conventional automated searching. By conducting a manual search of the CSD and literature, a list of over 1800 chiral species capable of conglomerate crystallization was curated by inspection of the racemic synthetic routes described in each publication. The majority of chiral conglomerate crystals are produced and published by synthetic chemists who seldom note and rarely exploit the implications this phenomenon can have on the enantiopurity of their crystalline materials. With their structures revealed, we propose that this list of compounds represents a new chiral pool which is not tied to biological sources of chirality.

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“…This highlights the possibility of utilizing conglomerate crystallisation as a new chiral pool. Within this list are C2 symmetrical pyrimidine (OBIPAR [76] ), phosphine (LUSZOO [77] ) and imidazole (ROJPOW [78] ) ligands, an atropsiomeric quinoline (TUWFAT [79] ), an α-methylpyridine (DOBWUN [80] ), and a chiral salen ligand (TUNMOF [81] ). Potential types of organocatalysts such as the C2 symmetrical diol (NULZEA [82] ), a PTC (phase transfer catalyst) crown ether (NOCNIC [83] ), and chiral phosphoric acid (CUVGAB [84] ), chiral ureas (RIPBUN, [85] AZUDAB [86] ), benzotetramisole (YAMBAS [87] ), amino-alcohol (HARFEN [88] ), and imidazole (PURJUJ [89] ) may also find use in asymmetric synthesis.…”

Section: Resultsmentioning

confidence: 99%

A Potentially Limitless Chiral Pool via Conglomerate Crystallisation: Unidentified Spontaneous Resolution in the CSD.

Walsh

Barclay

Begg

et al. 2022

Preprint

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Conglomerate crystallisation is the behaviour responsible for spontaneous resolution and the discovery of molecular chirality by Pasteur. The phenomenon of conglomerate crystallisation of chiral organic molecules has been left largely undocumented and offers synthetic chemists a potential new chiral pool not reliant on biological systems to supply stereochemical information. While other crystallographic behaviours can be interrogated by automated searching, conglomerate crystallisations are not identified within the Cambridge Structural Database (CSD) and are therefore not accessible by conventional means. By conducting a manual search of the CSD, a list of over 1,700 chiral species capable of conglomerate crystallisation was curated by inspection of the synthetic routes described in each publication. The majority of these are produced by synthetic chemists who seldom note and rarely exploit the implications this phenomenon can have on the enantioenrichment of their crystalline materials. We propose that this list represents a limitless chiral pool which will continually grow in size as more conglomerate crystals are synthesised and recorded.

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1-[2-(2,6-Diisopropylanilino)-1-naphthyl]isoquinoline

Cited by 4 publications

References 14 publications

Synthesis, characterization and phosphotriesterase mimetic activity of some Zn(II) and Cu(II) complexes

Synthesis, characterization and phosphotriesterase mimetic activity of some Zn(II) and Cu(II) complexes

Identifying a Hidden Conglomerate Chiral Pool in the CSD

A Potentially Limitless Chiral Pool via Conglomerate Crystallisation: Unidentified Spontaneous Resolution in the CSD.

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