Day: January 5, 2023

(1-Butyl-4-methyl-pyridinium)[Cu(SCN)₂]: A Coordination Polymer and Ionic Liquid was written by Spielberg, Eike T.;Edengeiser, Eugen;Mallick, Bert;Havenith, Martina;Mudring, Anja-Verena. And the article was included in Chemistry – A European Journal in 2014.Application of 65350-59-6 This article mentions the following:

The compound (C₄C₁py)[Cu(SCN)₂] (1), (C₄C₁py = 1-Butyl-4-methyl-pyridinium), which can be obtained from CuSCN and the ionic liquid (C₄C₁py)(SCN), turns out to be a new organic-inorganic hybrid material as it qualifies both, as a coordination polymer and an ionic liquid It features linked [Cu(SCN)₂]^– units, in which the thiocyanates bridge the copper ions in a μ_1,3-fashion. The resulting one-dimensional chains run along the a axis, separated by the C₄C₁py counterions. Powder x-ray diffraction not only confirms the single-crystal X-ray structure solution but proves the reformation of the coordination polymer from an isotropic melt. However, the materials shows a complex thermal behavior often encountered for ionic liquids such as a strong tendency to form a supercooled melt. At a relatively high cooling rate, glass formation is observed When heating this melt in DSC and temperature-dependent polarizing optical microscopy (POM), studies reveal the existence of a less thermodynamically stable crystalline polymorph. Raman measurements conducted at 10 and 100° point towards the formation of polyanionic chain fragments in the melt. Solid-state UV/visible spectroscopy shows a broad absorption band around 18,870 cm^-1 (530 nm) and another strong one <20,000 cm^-1 (<500 nm). The latter is attributed to the d(Cu^I)→π*(SCN)-MLCT (metal-to-ligand charge transfer) transition within the coordination polymer yielding an energy gap of 2.4 eV. At room temperature and upon irradiation with UV light, the material shows a weak fluorescence band at 15,870 cm^-1 (630 nm) with a quantum efficiency of 0.90(2)% and a lifetime of 131(2) ns. Upon lowering the temperature, the luminescence intensity strongly increases. Simultaneously, the band around 450 nm in the excitation spectrum decreases. In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6Application of 65350-59-6).

1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6) belongs to pyridine derivatives. The pyridine ring occurs in many important compounds, including agrochemicals, pharmaceuticals, and vitamins. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Application of 65350-59-6

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Evaluation of amphiphilic properties of fulvic acid and humic acid by alkylpyridinium binding study was written by Yee, Min Min;Miyajima, Tohru;Takisawa, Noboru. And the article was included in Colloids and Surfaces, A: Physicochemical and Engineering Aspects in 2006.HPLC of Formula: 104-73-4 This article mentions the following:

Amphiphilic properties of Aso fulvic acid (AFA) and Aso humic acid (AHA) were evaluated through a study on the binding of N-alkylpyridinium bromide (C_nPy⁺Br^–, n = 12, 14 and 16), with a potentiometric titration method with surfactant-ion-selective membrane electrodes in aqueous solution of pH 9.18 and ionic strength of 0.03 M at 25°. Different binding behaviors were observed between AFA and AHA due to the differences in the d. of carboxylate groups as well as hydrophobicity-hydrophilicity balance. Independent sites binding behavior was observed in the C_nPy⁺-AHA system; however, cooperative binding was observed in C_nPy⁺-AFA system. The binding of C_nPy⁺ to AHA was stronger than that to AFA, reflecting the importance of hydrophobic interaction between surfactant mols. and the backbone of AHA mols. The chain length dependence of the free energy of binding per CH₂ group amounted to about 3.1 kJ/mol in C_nPy⁺-AFA system, which is comparable to C_nPy⁺ binding to dextran sulfate, and that for the C_nPy⁺-AHA system was 2.3 kJ/mol. In the experiment, the researchers used many compounds, for example, 1-Dodecylpyridin-1-ium bromide (cas: 104-73-4HPLC of Formula: 104-73-4).

1-Dodecylpyridin-1-ium bromide (cas: 104-73-4) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.HPLC of Formula: 104-73-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Synthesis and crystal structure of [CuL_0.5(Ac)₂]_n·0.5nCHCl₃ (L = 2,5-bis(4-pyridyl)-1,3,4-oxadiazole) was written by Liu, He;Zhong, Bo-Hua;Liu, Li-Ping;Han, Shi-Tian. And the article was included in Journal of Chemical Crystallography in 2004.Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole This article mentions the following:

A 1-dimensional complex [CuL_0.5(Ac)₂]_n·0.5nCHCl₃ (L = 2,5-bis(4-pyridyl)-1,3,4-oxadiazole) was synthesized and structurally characterized by x-ray diffraction: Monoclinic, space group C2/c with a 27.217(3), b 13.0383(11), c 8.5671(9) Å, β 103.215(3)°, Z = 8. The crystal structure of the complex reveals that the familiar lantern-type structure that is characteristic of dimetal tetracarboxylates of Cu^II ions, and the binuclear units were bridged by the angular ligands to form a 1-dimensional zigzag chain coordination polymer. Every metal center is present in a distorted square-pyramidal coordination environment, consisting of coordination with one N atom of the ligand in the axial position and four O atoms of CH₃COO^– anions in equatorial positions. The Cu^II···Cu^II distance is 2.6060(9) Å. The title complex resides in the formation of a 3-dimensional network through π-π stacking interactions. In the experiment, the researchers used many compounds, for example, 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole).

2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole (cas: 15420-02-7) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Safety of 2,5-Di(pyridin-4-yl)-1,3,4-oxadiazole

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Theoretical Probing of Weak Anion-Cation Interactions in Certain Pyridinium-Based Ionic Liquid Ion Pairs and the Application of Molecular Electrostatic Potential in Their Ionic Crystal Density Determination: A Comparative Study Using Density Functional Approach was written by Joseph, Aswathy;Thomas, Vibin Ipe;Zyla, Gawel;Padmanabhan, A. S.;Mathew, Suresh. And the article was included in Journal of Physical Chemistry A in 2018.Safety of 1-Butyl-4-methylpyridin-1-ium bromide This article mentions the following:

A comprehensive study on the structure, nature of interaction, and properties of six ionic pairs of 1-butylpyridinium and 1-butyl-4-methylpyridinium cations in combination with tetrafluoroborate (BF₄^–), chloride (Cl^–), and bromide (Br^–) anions have been carried out using d. functional theory (DFT). The anion-cation interaction energy (ΔE_int), thermochem. values, theor. band gap, MO energy order, DFT-based chem. activity descriptors [chem. potential (μ), chem. hardness (η), and electrophilicity index (ω)], and distribution of d. of states (DOS) of these ion pairs were investigated. The ascendancy of the -CH₃ substituent at the fourth position of the 1-butylpyridinium cation ring on the values of ΔE_int, theor. band gap and chem. activity descriptors was evaluated. The ΔE_int values were neg. for all six ion pairs and were highest for Cl^– containing ion pairs. The theor. band gap value after -CH₃ substitution increased from 3.78 to 3.96 eV (for Cl^–) and from 2.74 to 2.88 eV (for Br^–) and decreased from 4.9 to 4.89 eV (for BF₄^–). Ion pairs of BF₄^– were more susceptible to charge transfer processes as inferred from their significantly high η values and comparatively small difference in ω value after -CH₃ substitution. The change in η and μ values due to the -CH₃ substituent is negligibly small in all cases except for the ion pairs of Cl^–. Critical-point (CP) analyses were carried out to investigate the AIM topol. parameters at the interionic bond critical points (BCPs). The RDG isosurface anal. indicated that the anion-cation interaction was dominated by strong H_cat···X_ani and C_cat···X_ani interactions in ion pairs of Cl^– and Br^– whereas a weak van der Waal’s effect dominated in ion pairs of BF₄^–. The mol. electrostatic potential (MESP)-based parameter ΔΔV_min measuring the anion-cation interaction strength showed a good linear correlation with ΔE_int for all 1-butylpyridinium ion pairs (R² = 0.9918). The ionic crystal d. values calculated by using DFT-based MESP showed only slight variations from exptl. reported values. In the experiment, the researchers used many compounds, for example, 1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6Safety of 1-Butyl-4-methylpyridin-1-ium bromide).

1-Butyl-4-methylpyridin-1-ium bromide (cas: 65350-59-6) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Safety of 1-Butyl-4-methylpyridin-1-ium bromide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Magnesiation of N-Heterocycles Using i-PrMgCl · LiCl and Catalytic Diisopropylamine was written by Nxumalo, W.;Dinsmore, A.. And the article was included in Synthetic Communications in 2015.Application of 644-98-4 This article mentions the following:

The direct magnesiation of various N-heterocyclic compounds with i-PrMgCl · LiCl and catalytic diisopropylamine allows for preparation of 2-substituted pyrroles, imidazole, indoles, and benzimidazoles, in moderate to good yields. The magnesiated substrates can readily undergo a Kumada-type coupling with iodo-aryls in the presence of catalytic Pd(PPh₃)₄. In the experiment, the researchers used many compounds, for example, 2-Isopropylpyridine (cas: 644-98-4Application of 644-98-4).

2-Isopropylpyridine (cas: 644-98-4) belongs to pyridine derivatives. Pyridine is diamagnetic and has a diamagnetic susceptibility of −48.7 × 10−6 cm3·mol−1.The molecular electric dipole moment is 2.2 debyes. The standard enthalpy of formation is 100.2 kJ·mol−1 in the liquid phase and 140.4 kJ·mol−1 in the gas phase. Halopyridines are particularly attractive synthetic building blocks in a variety of cross-coupling methods, including the Suzuki-Miyaura cross-coupling reaction.Application of 644-98-4

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

O-Substituted pyridine N-oxide derivatives. I. N-(Trimethylammoniumethoxy)pyridinium compounds, a new type of choline derivatives was written by Augustinsson, Klas Bertil;Hasselquist, Hans. And the article was included in Acta chem. Scand. in 1961.Name: 3,5-Dimethylpyridine 1-oxide This article mentions the following:

Treating the N-oxides of pyridine and the picolines without solvent at approx. 120° and N-oxides of 4-picoline and of the lutidines in acetonitrile at reflux temperature with bromocholine gave the title compounds The reaction of 2,6-lutidine N-oxide was carried out at 100° in the presence of water under pressure. The N-oxide of 2,5-lutidine, prepared by H₂O₂ in AcOH, b. 149°; picrate m. 128-9° (EtOH). The 3,5-isomer b₂₃ 166-8°, hygroscopic solid (C₆H₆). Also were prepared: 75% N-(2-trimethylammoniumethoxy)pyridinium dibromide, m. 198°; 51% N-(2-trimethylammoniumethoxy)-2-picolinium dibromide, m. 196°; 14% 3-isomer, m. 175°; 50% 4-isomer, m. 190°; 67% N-(2-trimethylammoniumethoxy)- 2,4-lutidinium dibromide, m. 195-5.5°; 49% 2,5-isomer, m. 191°; 9.5% 2,6-isomer, m. 175-5.5°; 100% 3,5-isomer, m. 196.5-7°. In the experiment, the researchers used many compounds, for example, 3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8Name: 3,5-Dimethylpyridine 1-oxide).

3,5-Dimethylpyridine 1-oxide (cas: 3718-65-8) belongs to pyridine derivatives. The ring atoms in the pyridine molecule are sp2-hybridized. The nitrogen is involved in the π-bonding aromatic system using its unhybridized p orbital. The lone pair is in an sp2 orbital, projecting outward from the ring in the same plane as the σ bonds. Pyridine groups exist in countless molecules, and their applications include catalysis, drug design, molecular recognition, and natural product synthesis.Name: 3,5-Dimethylpyridine 1-oxide

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Flow Microreactor Technology for Taming Highly Reactive Chloroiodomethyllithium Carbenoid: Direct and Chemoselective Synthesis of α-Chloroaldehydes was written by Musci, Pantaleo;Colella, Marco;Sivo, Alessandra;Romanazzi, Giuseppe;Luisi, Renzo;Degennaro, Leonardo. And the article was included in Organic Letters in 2020.Recommanded Product: Phenyl(pyridin-2-yl)methanone This article mentions the following:

A straightforward flow synthesis of α-chloro aldehydes has been developed. The strategy involves, for the first time, the thermal unstable chloroiodomethyllithium carbenoid and carbonyl compounds A batch vs. flow comparative study showcases the superb capability of flow technol. in prolonging the lifetime of the lithiated carbenoid, even at -20°C. Remarkably, the high chemoselectivity realized in flow allowed for preparing polyfunctionalized α-chloro aldehydes not easily accessible with traditional batch procedures. In the experiment, the researchers used many compounds, for example, Phenyl(pyridin-2-yl)methanone (cas: 91-02-1Recommanded Product: Phenyl(pyridin-2-yl)methanone).

Phenyl(pyridin-2-yl)methanone (cas: 91-02-1) belongs to pyridine derivatives. Pyridine has a dipole moment and a weaker resonant stabilization than benzene (resonance energy 117 kJ·mol−1 in pyridine vs. 150 kJ·mol−1 in benzene). Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Recommanded Product: Phenyl(pyridin-2-yl)methanone

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Trifluoromethylation of Aryl and Heteroaryl Halides with Fluoroform-Derived CuCF₃: Scope, Limitations, and Mechanistic Features was written by Lishchynskyi, Anton;Novikov, Maxim A.;Martin, Eddy;Escudero-Adan, Eduardo C.;Novak, Petr;Grushin, Vladimir V.. And the article was included in Journal of Organic Chemistry in 2013.Related Products of 116308-35-1 This article mentions the following:

Fluoroform-derived CuCF₃ recently discovered in our group exhibits remarkably high reactivity toward aryl and heteroaryl halides, performing best in the absence of extra ligands. A broad variety of iodoarenes undergo smooth trifluoromethylation with the “ligandless” CuCF₃ at 23-50 °C to give the corresponding benzotrifluorides in nearly quant. yield. A number of much less reactive aromatic bromides also have been trifluoromethylated, including pyridine, pyrimidine, pyrazine, and thiazole derivatives as well as aryl bromides bearing electron-withdrawing groups and/or ortho substituents. Only the most electrophilic chloroarenes can be trifluoromethylated, e.g., 2-chloronicotinic acid. Exceptionally high chemoselectivity of the reactions (no side-formation of arenes, biaryls, and C₂F₅ derivatives) has allowed for the isolation of a large number of trifluoromethylated products in high yield on a gram scale (up to 20 mmol). The CuCF₃ reagent is destabilized by CuX coproduced in the reaction, the magnitude of the effect paralleling the Lewis acidity of CuX: CuCl > CuBr > CuI. While S_NAr and S_RN1 mechanisms are not operational, there is a well-pronounced ortho effect, i.e., the enhanced reactivity of ortho-substituted aryl halides 2-RC₆H₄X toward CuCF₃. Intriguingly, this ortho-effect is observed for R = NO₂, COOH, CHO, COOEt, COCH₃, OCH₃, and even CH₃, but not for R = CN. The fluoroform-derived CuCF₃ reagent and its reactions with haloarenes provide an unmatched combination of reactivity, selectivity, and low cost. In the experiment, the researchers used many compounds, for example, 2-(Trifluoromethyl)nicotinaldehyde (cas: 116308-35-1Related Products of 116308-35-1).

2-(Trifluoromethyl)nicotinaldehyde (cas: 116308-35-1) belongs to pyridine derivatives. Pyridine has a conjugated system of six π electrons that are delocalized over the ring. The molecule is planar and, thus, follows the Hückel criteria for aromatic systems. One of the examples of pyridines is the well-known alkaloid lithoprimidine, which is an A3 adenosine receptor antagonist and N,N-dimethylaminopyridine (DMAP) analog, commonly used in organic synthesis.Related Products of 116308-35-1

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

A metabolomic approach to investigate effects of ocean acidification on a polar microalga Chlorella sp. was written by Tan, Yong-Hao;Lim, Phaik-Eem;Beardall, John;Poong, Sze-Wan;Phang, Siew-Moi. And the article was included in Aquatic Toxicology in 2019.Related Products of 626-64-2 This article mentions the following:

Ocean acidification, due to increased levels of anthropogenic carbon dioxide, is known to affect the physiol. and growth of marine phytoplankton, especially in polar regions. However, the effect of acidification or carbonation on cellular metabolism in polar marine phytoplankton still remains an open question. There is some evidence that small chlorophytes may benefit more than other taxa of phytoplankton. To understand further how green polar picoplankton could acclimate to high oceanic CO₂, studies were conducted on an Antarctic Chlorella sp. Chlorella sp. maintained its growth rate (∼0.180 d^-1), photosynthetic quantum yield (Fv/Fm = ∼0.69) and chlorophyll a (0.145 fg cell^-1) and carotenoid (0.06 fg cell^-1) contents under high CO₂, while maximum rates of electron transport decreased and non-photochem. quenching increased under elevated CO₂. GCMS-based metabolomic anal. reveal that this polar Chlorella strain modulated the levels of metabolites associated with energy, amino acid, fatty acid and carbohydrate production, which could favor its survival in an increasingly acidified ocean. In the experiment, the researchers used many compounds, for example, Pyridin-4-ol (cas: 626-64-2Related Products of 626-64-2).

Pyridin-4-ol (cas: 626-64-2) belongs to pyridine derivatives. In contrast to benzene, Pyridine’s electron density is not evenly distributed over the ring, reflecting the negative inductive effect of the nitrogen atom. Reduced pyridines, namely tetrahydropyridines, dihydropyridines and piperidines, are found in numerous natural and synthetic compounds. The synthesis and reactivity of these compounds have often been driven by the fact many of these compounds have interesting and unique pharmacological properties. Related Products of 626-64-2

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem

Different bonds cleavage of arenesulfonates: access to diverse aryl ethers was written by Fang, Yongsheng;Li, Wenhui;Lin, Jianying;Li, Xing. And the article was included in Huaxue Xuebao in 2021.Computed Properties of C5H5NO This article mentions the following:

Aryl alkyl ethers and diaryl ethers represent ubiquitous structural motifs in natural products, medicinally relevant compounds, biol. active compounds, agrochems. and organic materials, and they are also useful building blocks in organic synthesis. Therefore, many transformations have been reported for the synthesis of these two kinds of compounds Among these versatile methods, transition-metal-free approaches using different reagents as starting materials have been developed as promising and alternative protocols. Although one example for transition-metal-catalyzed transformation of arenesulfonates into aryl alkyl ethers and diaryl ethers has been reported, there are no reports about the formation of aryl ethers utilizing arenesulfonates as starting materials via a transition-metal-free protocol, and existing methods for providing sterically hindered ortho-substituted diaryl ethers using electrophiles substituted by electron-deficient groups, particularly by a bulky one at the ortho-position as starting materials are very rare. We will report a K₂CO₃-mediated method for the synthesis of aryl alkyl ethers using arenesulfonates as starting materials via two alternative paths. One path is the cross-coupling of aryl arenesulfonates with alcs. through their S-O bond cleavage, and the other uses the reactions of alkyl arenesulfonates with phenols via their C-O bond cleavage. Addnl., we also report the K₃PO₄^–promoted preparation of bulky ortho-substituted diaryl ethers via the C-S bond cleavage of aryl arenesulfonates or arenesulfonyl chlorides bearing electron-withdrawing groups at 2-, 2,4- or 2,6-position of the Ph ring in the presence of phenols, resp. General procedure for the reactions of aryl arenesulfonates with various alcs.: to an oven-dried glass tube, aryl arenesulfonate 1 (0.2 mmol), K₂CO₃ (2 equivalent) and 0.5 mL alc. 2 were added in turn. The reaction system was then stirred at 65°C until the aryl arenesulfonate 1 was completely consumed as determined by thin layer chromatog. Finally, the reaction mixture was purified by silica gel column chromatog. to afford the desired product 3. General procedure for the reactions of aryl o-substituted arenesulfonates with the corresponding phenols: to an oven-dried glass tube, aryl o-substituted arenesulfonate 7 (0.2 mmol), K₃PO₄ (3 equivalent), the corresponding phenol 5 (1.2 equivalent) and 1.0 mL toluene were added in turn. The reaction system was then stirred at 100°C until the reaction was over as determined by TLC. Finally, the reaction mixture was purified by silica gel column chromatog. to afford the desired product 8. In the experiment, the researchers used many compounds, for example, Pyridin-4-ol (cas: 626-64-2Computed Properties of C5H5NO).

Pyridin-4-ol (cas: 626-64-2) belongs to pyridine derivatives. Pyridine’s the lone pair does not contribute to the aromatic system but importantly influences the chemical properties of pyridine, as it easily supports bond formation via an electrophilic attack. Pyridine, its benzo and pyridine-based compounds play diverse roles in organic chemistry. Pyridine-based materials are valued for their optical and physical properties as well as their medical potential. Computed Properties of C5H5NO

Referemce:
Pyridine – Wikipedia,
Pyridine | C5H5N – PubChem