Synthesis, crystal structures and thermal behaviour of organic–inorganic hybrids incorporating a chiral diamine

Hajlaoui, Fadhel; Naı̈li, Houcine; Yahyaoui, Samia; Norquist, Alexander J.; Mhiri, Tahar; Bataille, Thierry

doi:10.1016/j.jorganchem.2011.11.023

Cited by 17 publications

(3 citation statements)

References 29 publications

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“…However, despite the similarities in compositions in compounds 3-7, distinct differences in three-dimensional packing are observed between the Zn II (3 and 6), Fe II (4), Cu II (5) and Co II (7). 20,22,23 Compounds 3, 4, 6 and 7 are all constructed from octahedrally coordinated transition metal cations coordinated by six water molecules [M(H 2 O) 6 ] 2+ , isolated sulfate anions (SO 4 ) 2− , and either [(R)-H 2 mpz] 2+ or [(S)-H 2 mpz] 2+ cations. The octahedra environments of M II (M II = Fe II , Co II and Zn II ) are not regular, as seen in other isostructural metal sulfates.…”

Section: Synthesis and Characterization Of The Saltsmentioning

confidence: 99%

“…1 and Table 1) were obtained by slow evaporation of water solutions containing metal(II) sulfates, sulfuric acid and either racemic or chiral cyclic diamine 2-methylpiperazine. [20][21][22][23] All the structures of 1-7 are related: the asymmetric units in each compound consist of organic cations, SO 4 tetrahedra and one M II cation octahedrally coordinated to six oxygen atoms, all being held together through extensive hydrogen-bonding networks. However, the symmetries of the synthesized salts differ greatly.…”

Section: Introductionmentioning

confidence: 99%

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2-Dihydromethylpiperazinediium-M^II(M^II= Cu^II, Fe^II, Co^II, Zn^II) double sulfates and their catalytic activity in diastereoselective nitroaldol (Henry) reaction

et al. 2013

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A series of double dihydromethylpiperazinediium metallic sulfates 1-7 [H(2)mpz]M(II)(SO(4))(2)·nH(2)O (mpz = 2-methylpiperazine, C(5)H(12)N(2)) are prepared by slow evaporation using a racemic (R/S)-mpz (for 1, 2) or enantiopure R-mpz (for 3), S-mpz (for 4-7) and sulfates of Cu(II) (for 5), Fe(II) (for 1, 4), Co(II) (for 7) and Zn(II) (for 2, 3, 6), and characterized by infrared spectroscopy, elemental analysis and single crystal X-ray diffraction. The [M(II)(H(2)O)(6)](2+), [(R/S)-H(2)mpz](2+), [(R)-H(2)mpz](2+) or [(S)-H(2)mpz](2+) cations and 2SO(4)(2-) anions are linked together via two types of hydrogen bonds, Ow-Hw···O and N-H···O, leading to supramolecular arrangements. The use of the racemic 2-mpz provides alternatives in crystallization: a centrosymmetric structure where the enantiomers are related by an appropriate crystallographic symmetry operation or one where the enantiomers occupy the same crystallographic position, generating disorder. Compounds 1-7 act as diastereoselective catalysts for the nitroaldol (Henry) reaction. The diastereoselectivity can be regulated from exclusive threo to exclusive erythro isomer preparation with typical yields of 50-99%, depending on the catalyst and the substrate used.

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Section: Synthesis and Characterization Of The Saltsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

2-Dihydromethylpiperazinediium-M^II(M^II= Cu^II, Fe^II, Co^II, Zn^II) double sulfates and their catalytic activity in diastereoselective nitroaldol (Henry) reaction

et al. 2013

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“…Nevertheless, a “single set of factors” that determines the dimensionality of the resulting framework of a hybrid organic–inorganic material has not been identified. Although many different organic molecule types have been used as templates − it is well-known that amines and diamines are very important building blocks in the synthesis of hybrid materials. − Paul et al and Liu et al present good examples of aromatic amines (specifically, polyazaheterocycles and triazole derivates) used as organic block and cadmium sulfates as inorganic part, where two-dimensional (2D) and 3D frameworks were synthesized. The use of different structural isomers as organic building blocks was previously studied by Thirumurugan and Rao and Zheng He et al Thirumurugan and Rao presented a group of hybrid compounds that contain isomers of benzenedicarboxylic acid as organic components in the presence or absence of amines, acting as chelating ligands, and Zn or Cd as metal centers.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, and Optical Properties of Organic–Inorganic Hybrid Layered Materials: A Solvent-Free Ligand-Controlled Dimensionality Approach Based on Metal Sulfates and Aromatic Diamines

Guillén

Oszajca

Luberda-Durnaś

et al. 2018

Crystal Growth & Design

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A new family of organic–inorganic hybrid layered materials based on cadmium and zinc sulfates was synthesized using 1,2-phenylenediamine (OPD), 1,3-phenylenediamine (MPD), and 1,4-phenylenediamine (PPD) as organic templates and ligands. The diamines act as structure-directing agents to obtain one-dimensional (1D), 2D, and 3D frameworks. Six new materials were obtained utilizing a simple, solvent-free synthesis approach: 1D: (OPD)2ZnSO4 1, (OPD)2CdSO4 2; 2D: (MPD)2ZnSO4 3, (MPD)2CdSO4 4; 3D: (PPD)ZnSO4 5, (PPD)CdSO4 6. The synthesis method proved to be scalable and robust. The crystal structures were determined using data from X-ray powder diffraction measurements (XRPD). It was observed that the type of amine determines the dimensionality of the obtained materials. 1D, 2D, and 3D structures were obtained using ortho-, meta-, and para-phenylenediamine isomers, respectively. The phase purity of the samples was confirmed by elemental analysis, and the morphology of the crystallites was studied using scanning electron microscopy. The thermal stability was determined by thermogravimetry and nonambient XRPD techniques. Additional characterization was performed for the two non-centrosymmetric, polar materials 3 and 4. Second-order nonlinear optical properties were examined using both experimental measurements (second harmonic generation) and theoretical calculations.

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Phase Transition Originating from Disorder–Order Transformation Coupled with Reorientation in the Organic–Inorganic Hybrid Compound (C₄H₁₄N₂)[Cd₂(H₂O)₆(SO₄)₃]

Chen

Zhang

et al. 2017

Eur J Inorg Chem

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The organic-inorganic hybrid compound 1,4-butyldiammonium hexaaquadicadmium(II) trisulfate (C 4 H 14 N 2 )[Cd 2 -(H 2 O) 6 (SO 4 ) 3 ] (1) was synthesized by the reaction of 3CdSO 4 ·8H 2 O with 1,4-butanediamine in sulfuric acid aqueous solution. Differential scanning calorimetry measurements indicate that 1 undergoes a reversible phase transition at 243.4 K with a thermal hysteresis of 3.3 K. Single-crystal X-ray diffraction data disclose that the phase transition is from the room-temperature phase with the space group C2/c to the low-temperature phase with the space group P1 with the Aizu notation of [a]

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Synthesis, crystal structures and thermal behaviour of organic–inorganic hybrids incorporating a chiral diamine

Cited by 17 publications

References 29 publications

2-Dihydromethylpiperazinediium-M^II(M^II= Cu^II, Fe^II, Co^II, Zn^II) double sulfates and their catalytic activity in diastereoselective nitroaldol (Henry) reaction

2-Dihydromethylpiperazinediium-M^II(M^II= Cu^II, Fe^II, Co^II, Zn^II) double sulfates and their catalytic activity in diastereoselective nitroaldol (Henry) reaction

Synthesis, Characterization, and Optical Properties of Organic–Inorganic Hybrid Layered Materials: A Solvent-Free Ligand-Controlled Dimensionality Approach Based on Metal Sulfates and Aromatic Diamines

Phase Transition Originating from Disorder–Order Transformation Coupled with Reorientation in the Organic–Inorganic Hybrid Compound (C₄H₁₄N₂)[Cd₂(H₂O)₆(SO₄)₃]

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Synthesis, crystal structures and thermal behaviour of organic–inorganic hybrids incorporating a chiral diamine

Cited by 17 publications

References 29 publications

2-Dihydromethylpiperazinediium-MII(MII= CuII, FeII, CoII, ZnII) double sulfates and their catalytic activity in diastereoselective nitroaldol (Henry) reaction

2-Dihydromethylpiperazinediium-MII(MII= CuII, FeII, CoII, ZnII) double sulfates and their catalytic activity in diastereoselective nitroaldol (Henry) reaction

Synthesis, Characterization, and Optical Properties of Organic–Inorganic Hybrid Layered Materials: A Solvent-Free Ligand-Controlled Dimensionality Approach Based on Metal Sulfates and Aromatic Diamines

Phase Transition Originating from Disorder–Order Transformation Coupled with Reorientation in the Organic–Inorganic Hybrid Compound (C4H14N2)[Cd2(H2O)6(SO4)3]

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2-Dihydromethylpiperazinediium-M^II(M^II= Cu^II, Fe^II, Co^II, Zn^II) double sulfates and their catalytic activity in diastereoselective nitroaldol (Henry) reaction

2-Dihydromethylpiperazinediium-M^II(M^II= Cu^II, Fe^II, Co^II, Zn^II) double sulfates and their catalytic activity in diastereoselective nitroaldol (Henry) reaction

Phase Transition Originating from Disorder–Order Transformation Coupled with Reorientation in the Organic–Inorganic Hybrid Compound (C₄H₁₄N₂)[Cd₂(H₂O)₆(SO₄)₃]