Author: tianli

Safety of Pyridine-3,5-dicarbonitrile. So far, in addition to halogen atoms, other non-metallic atoms can become part of the aromatic heterocycle, and the target ring system is still aromatic. Compound: Pyridine-3,5-dicarbonitrile, is researched, Molecular C7H3N3, CAS is 1195-58-0, about Dihydropyridines. XVII. π-Electronic structure and reactivity of alkyl 3,5-dicyanopyridines.

The π-electronic structure of alkyl 3,5-dicyanopyridines was studied by the Hueckel M.O. L.C.A.O. method. The heteroatom model was used in the calculations The exptl. course of nucleophilic reactions was in agreement with the calculated superdelocalizabilities. Some of the exptl. excitation energies depended linearly on the calculated transition energies. Correlation was found between the values of proton shifts in the N.M.R. spectra of dicyanopyridines and the corresponding electron densities.

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Volke, J.; Skala, V. published an article about the compound: Pyridine-3,5-dicarbonitrile( cas:1195-58-0,SMILESS:N#CC1=CC(C#N)=CN=C1 ).Category: alcohols-buliding-blocks. Aromatic heterocyclic compounds can be classified according to the number of heteroatoms or the size of the ring. The authors also want to convey more information about this compound (cas:1195-58-0) through the article.

Electrochem. reduction of mono- and dicyanopyridines at a Hg electrode proceded via intermediates containing a cyclic π-electron septet formed after uptake of the 1st electron; these intermediates underwent either protonation, dimerization, or further 1-electron reduction, depending on the position of the cyano group(s), the acidity of the medium, and the electrode potential. This mechanism was substantiated by LCAO-MO and SCF calculations; the exptl. half-wave potentials were correlated to the energy of the lowest free MO of the substrate.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《Reaction of Grignard reagent with 3,5-dicyanopyridines》. Authors are Lukes, R.; Kuthan, J..The article about the compound:Pyridine-3,5-dicarbonitrilecas:1195-58-0,SMILESS:N#CC1=CC(C#N)=CN=C1).Application of 1195-58-0. Through the article, more information about this compound (cas:1195-58-0) is conveyed.

Et2O solutions of 3,5-dicyanopyridines reacted at 20-40° with MeMgI (Ia) or EtMgBr (Ib) in 4-6-fold excess to form NH.CR1:C(CN).CR2:C(CN).CHR3 or NH.CR1:C(CN).CHR2.C(CN):CR3. The following were prepared: R1 = R2 = R3 = H (I); R1 = R2 = H, R3 = Me (II); R1 = R3 = H, R2 = Et (III); R1 = Me, R2 = R3 = H (IV); R1 = R3 = Me, R3 = H (V); R1 = R3 = Me, R2 = H (VI); R1 = H, R2 = R3 = Me (VII); R1 = H, R2 = Me, R3 = Et (VIII); R1 = H, R2 = Et, R3 = Me (IX); R1 = R3 = Me, R2 = H (X); R1 = R2 = R3 = Me (XI); R1 = R2 = H, R3 = Me (XII); R1 = R3 = H, R2 = Et (XIII); R1 = R2 = Me, R3 = H (XIV); R1 = R2 = R3 = Me (XV). I with Ia gave 76% XII, I with Ib 65% XIII, II with Ia 66% VII, II with Ib 48% VIII, III with Ia 89% IX, IV with Ia about 43% X and XIV, V with Ia 82% XI, VI with Ia 35% XV.

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The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《o-Halogenated p-nitroaniline and its derivatives》. Authors are Korner, G.; Contardi.The article about the compound:3-Bromo-4-chloronitrobenzenecas:16588-26-4,SMILESS:BrC1=C(C=CC(=C1)[N+](=O)[O-])Cl).Product Details of 16588-26-4. Through the article, more information about this compound (cas:16588-26-4) is conveyed.

When p-NO2C6H4NH2 is dissolved or suspended in HCl and Cl or Br added a mixture, difficult to sep., of mono- and dihalogenated anilines with the halogen in the o-position is formed. If, however, gaseous Cl (mol. ratio 1 : 1) is passed into the b. HCl solution 2,4-Cl(O2N)C6H3NH2 is almost the sole product. This derivative mixed with some di-Cl derivative is obtained on chlorinating at -o°(Casella & Co., Ger. Pat., 109,189). At room temperature, on adding Cl slowly to the HCl solution, the di-Cl deriv, + quinone are formed. Chlorinating by Noelting’s method, using Ca(ClO)2, gave mixtures Similar results were obtained with Br. These derivatives are obtained by warming 1-nitro-3,4-dibromo (or dichloro) benzene with alc. NH3 in the scaled tube at 190°. The NH2 group substitutes p to NO2. By halogenating these monohalogen derivatives it is possible to get derivatives with 2 different halogens in the same ring. The action of ClI on a glac. AcOH solution of p-NO2C6H4NH2 gives mixtures from which the mono- and di-I derivatives can be separated by EtOH. 1-Nitro-3-chloro-4-aniline, bright yellow needles from hot H2O, m. 104.5°; acetyl derivative, straw-yellow flat prisms from EtOH, m. 139°. Diazotizing in H2SO4 or HNO3 suspension with gaseous HNO2 gives the diazo compound which, by way of the perbromide, goes into 1-nitro-3-chloro-4-bromobenzene, prisms from CHCl2, m. 62°. 1-Nitro-3-chloro-4-iodobenzene, almost colorless needles from EtOH, m. 103°, is obtained similarly, by way of the periodide. 1-Nitro-3-bromo-4-aniline, bright yellow needles, m. 104.5°, which with Ac2O gives the monoacetyl derivative, flat prisms, m. 114°, and the diacetyl derivative, short fat prisms, m. 132°. also from the mono derivative, by the action of Ac2O + traces of POCl3. Diazotizing and halogenating as above gives 1-nitro-3-bromo-4-chlorobenzene, white or colorless prisms, volatil with steam, m. 61°, is identical with the compound similarly obtained from 2,5-Cl(O2N)C6H3NH2. 1-Nitro-3-bromo-4-iodobenzene, prisms from AcOEt, m. 106°, was obtained similarly. 1-Nitro-3-iodo-4-aniline presents 2 forms: (1) stable yellow-red prisms, and (2) the labile forms golden yellow plates in C6H6, below 17°, m. 109°; monoacetyl derivative, bright yellow prisms; diacetyl derivative, more soluble than the mono compound, white needles. The diazo compound, on adding Cl, gives 1-nitro-3-iodo-4-chlorobenzene, needles, m. 78°, identical with the compound obtained similarly with I from 2,5-Cl(O2N)C6H2NH2. 1-Nitro-3,5-dichloro-4-aniline, yellow shining needles, m. 195°, slightly soluble in dilute and concentrate inorganic acids, unchanged by fuming HNO3 in the cold. To diazotize suspend in HNO3 (d. 1.38) and add gaseous HNO2 at o°; on diluting the explosive diazonium nitrate seps., fairly soluble in H2O. Ac2O + traces of POCl3 give the monoacetyl derivative, almost colorless needles, m. 215°, and the diacetyl derivative, monoclinic (Artini, Rend. ist. lombardo sci. lett., [2] 45, 1912), prisms, m. 142.5°, d. 1.565, more soluble than the mono compound In absolute EtOH + some concentrate H2SO4 + EtONO it gives 1-nitro-3,5-dichlorobenzene, plates, m. 65.4°, which on reducing with Sn + HCl gives 3,5-dichloroaniline, needles, m. 51.5°. The latter, by replacing NH3 with Cl, gives 1,3,4-trichlorobenzene, white needles, to. 63.5°, which is also obtained from 2,4,6-Cl3C8H2NH2, m. 77.5°, by replacing NH3, with H. 3,5-Cl2C4H3NH2 by replacing NH2 with Br gave 1-bromo-3,5-dichlorobenzene, needles, m. 75.8°. 1-Iodo-3,5-dichlorobenzene, m. 54°, was obtained similarly and is identical with that prepared similarly from 2,4,6-ICl2C6H2NH2, m. 84°. Anilines containing 3 identical halogen ats. in the 2,4,6-positions may be obtained by direct halogenation of PhNH2 of which they are the end products. The mixed halogenated anilines are made from anilines halogenated in p-position by adding two halogens (Br or ClI) in the o-position in glac. AcOH. o,p- or o,o-dihalogenanilines may even be used, but displacing of weak halogens may take place. All of the theoretically possible trihalogenbenzenes can be obtained by thus substituting halogen for NH2 in anilines. 2,6,4-Cl2(O2N)C6H2NH2 gives 1-nitro-3,4,5-trichlorobenzene, bright yellow prisms, m. 72.5°, volatil with steam; reduction and elimination of NH2 gives 1,2,3-C6H2Cl3, identical with that from 2,6-Cl2C6H3NH2 by the same method. 1-Nitro-3,5-dichloro-4-bromobenzene, from the above aniline, yellow. prisms, m. 88°, volatile with steam; similarly 1-nitro-3,5-dichloro-4-iodobenzene, yellow prisms, m. 154.8°, less volatile; reduction, etc., gives 1,3-dichloro-2-iodobenzene, thin plates, m. 68°, volatile with steam, also from 3,6-C;2C4H3NH2 with I. p-NO3 C4H4NH2 + Br gives 1-nitro-3,5-dibromo-4-aniline, yellow plates, m. 202.5°; Ac2O as above gives the monoacetyl derivative, colorless needles or triclinic prisms, isomorphous with the di-Cl compound, and the diacetyl derivative, prisms, m. 136°, triclinic pinacoidal, a : b : c = 1.0901 : 1 : 0.8325, a = 88° 43′ 4”. β = 70° 49′ 34”. γ = 93° 25′ 39”, d. 1.939.3 Diazotizing the above or 2,4.6-Br2(O2N)C5H2NH3 with EtONO, etc., gives 1-nitro-3,5-dibromobenzene, almost colorless needles, m. 104.5°; on reduction with Sn + HCl, etc., it gives sym.-dibromochlorobenzene, m. 119°, with Cl, or dibromoiodobenzene, m. 124.8°, with 1. Both are easily volatil with steam and may be prepared from the corresponding anilines and the latter also from 2,4,6-IBr2C6H2NH2. 1-Nitro-3,4,5-tribromobenzene, from the o,o-dibromoaniline by replacing NH3 with Br, yellowish prisms, m. 111.9° on reduction, etc., gives 1,2,3-C6H3Br3, m. 87.8°. 1-Nitro-3,5-dibromo-4-chlorobenzene from the same aniline, yellowish prisms, m. 92-7°, on reduction, etc., gives 2,6-Br2C6H3Cl, m. 71°, identical with the compound similarly obtained from 2,6-Br2C6H3NH2 by replacing NH2 with Cl. 1-Nitro-3,5-dibromo-4-iodobenzene, from 2,6,4-Br2(O2N)C6H2NH2, prisms, 135.5°, cannot be reduced to the aniline. The 2,6-Br2C6H2I was obtained from 2,6-Br2C6H3NH2, prisms, m. 72°. 1-Nitro-3,5-diiodo-4-aniline, from p-NO2C6H4NH2 + ClI in AcOH, yellow needles; m. 245°; monoacetyl derivative, yellow needles, m. 249°; diacetyl derivative, paler yellow prisms, m. 171°, triclinic pinacoidal, a : b : c = 0.9682 : 1 : O.7260, α = 83° 6’43”, β = 76°8’29”, γ = 99° 42′ 44”, d. 2.290. 1-Nitro-3,5-diiodobenzene, from the preceding, difficultly volatile with steam, yellowish prisms, m. 104.5°, on reducing with FeSO4 + NH3 gives 3,5-I2C6H2NH3, needles, m. 110°. 2,6,4-I2ClC6H2NH2 gave 1,3-diiodo-5-chlorobenzene, needles, m. 101°, discolors brown in the light. Similarly the 5-bromoaniline gave 1,3-diiodo-5-bromobenzene, m. 140°, slightly volatile with steam. 1,3,5-Triiodobenzene, from 2,4,6-I2C6H2NH2 or 3.5-I2C6H3NH2, opaque needle, m. 184.2°. Decompose of 2,6,4-I2(O2N)C6H2N2NO3 with b. aqueous Cu2Cl2 gave 1-nitro-3,5-diiodo-4-chlorobenzene, needles, m. 110°; reduction with FeSO4 + NH3 gives a poor yield, (NH4)2S gives a better yield of the aniline together with some S-containing compound The aniline gives 2,6-I2C6H3Cl, rhombic plates, m. 82°. 2,6,4-I2(O2N)(C6H2NH2 gives 1-nitro-3,5-diiodo-4-bromobenzene, white needles from EtOH, yellow prisms from CHCl3 m. 125.4°, and 1-nitro-3,4,5-triiodobenzene, yellow prisms from EtOH, contain C6H6 of crystallization when crystallized from C6H6; reduction with FeSO4 + NH3 gives 3,4,5-triiodoaniline with difficulty; (NH4)2S gives sym.-I2C6H2NH2. The I2C6H2NH2 gives 1,2,3-C6H2I2 on changing NH2 for H, m. 116°, which is identical with that from 2,3-I2C6H3NH2. 2,4-Cl(O2N)C6H3NH2 + Br gives 1-nitro-3-chloro-5-bromo-4-aniline, bright Yellow needles, m. 177.4°; monoacetyl derivative, straw-yellow needles, m. 224°; diacetyl derivative, prisms or plates, m. 139°, monoclinic, prismatic, a : b : c = 1.1127 : 1 : 0.8509, β = 70-36°, d. 1-749. 1-Nitro-3-chloro-5-bromobenzene, from the above aniline, plates, m. 81.2°. and this on reducing with Sn + HCl, etc., gives 3-chloro-5-bromoaniline, needles, or prisms. The latter, as well as 2,4,6-BrClIC6H2NH2, m. 110.5°, gives 1-chloro-3-bromo-5-iodobenzene, needles, m. 85.8°. 1-Nitro-3,4-dichloro-5-bromobenzene, yellowish prisms, m. 82.5°, 1-Nitro-3,4-dibromo-5-chlorobenzene, yellowish prisms, m. 99.5°, and 1-nitro-3-chloro-4-iodo-5 bromobenzene, needles, 159°, by replacing NH2 with a halogen in the preceding nitroaniline. 1,2-Dibromo-3-chlorobenzene, by reducing 3,4,5-Br2ClC6H2NO2, rhombic plates. m. 72.6°. 2,4-Cl(O2N)C6H2NH22, in HOAc + ClI gives 1-nitro-3-chloro-5-iodo-4-aniline, bright yellow needles, 195°; monoacetyl derivative, white prisms, m. 207°; diacetyl derivative, prisms, m. 113°, monoclinic, a : b : c = 1.038 :-1 : 0.799, β = 71.44°, d. 1.913. This aniline gives 1-nitro-3-chloro-5-iodobenzene, yellow prisms, m. 70.4° by replacing NH2 with Cl. 1-Nitro-3,4-dichloro-5-iodobenzene, from the aniline with Cl, bright yellow prisms, m. 59°, is not easily reduced by FeSO4 + NH3, but Sn + HCl gives 3,5-CHC6H3NH2, plates, m. 69.8°; with Br the aniline gives 1-nitro-3-chloro-4-bromo-5-iodobenzene, almost colorless needles, m. 95°; and with I it gives 1-nitro-3-chloro-4,5-diiodobenzene, almost colorless needles, m. 146.5°. 3,4,5-Cl2IC6H2NO2 + (NH4)2S in EtOH gives 3,4-Cl2C6H3NH2. 2,4-Br(O2N)C6H3NH2 + CH in HOAc gives 1-nitro-3-bromo-5-iodo-4-aniline, needles, m. 221°; monoacetyl derivative, yellowish prisms, m. 226°; diacetyl derivative, prisms, m. 134°, triclinic pinacoidal, a : b : C = 0.9470 : 1 : 0.7288, α = 83° 59′ 54”, β = 77° 30′ 18”, γ = 99° 6′ 14”, d.2.112. 1-Nitro-3-bromo-5-iodobenzene, by replacing NH2 with H in the preceding aniline, needles, m. 97.5°; 1-nitro-3-bromo-4-chloro-5-iodobenzene, by replacing NH2 with Cl, yellowish prisms or colorless needles, m. 84°.

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Recommanded Product: 6-Bromo-5-iodopyridin-3-amine. The reaction of aromatic heterocyclic molecules with protons is called protonation. Aromatic heterocycles are more basic than benzene due to the participation of heteroatoms. Compound: 6-Bromo-5-iodopyridin-3-amine, is researched, Molecular C5H4BrIN2, CAS is 697300-68-8, about 5-Substituted Derivatives of 6-Halogeno-3-((2-(S)-azetidinyl)methoxy)pyridine and 6-Halogeno-3-((2-(S)-pyrrolidinyl)methoxy)pyridine with Low Picomolar Affinity for α4β2 Nicotinic Acetylcholine Receptor and Wide Range of Lipophilicity: Potential Probes for Imaging with Positron Emission Tomography. Author is Zhang, Yi; Pavlova, Olga A.; Chefer, Svetlana I.; Hall, Andrew W.; Kurian, Varughese; Brown, LaVerne L.; Kimes, Alane S.; Mukhin, Alexey G.; Horti, Andrew G..

Potential positron emission tomog. (PET) ligands with low picomolar affinity at the nicotinic acetylcholine receptor (nAChR) and with lipophilicity (log D) ranging from -1.6 to +1.5 have been synthesized. Most members of the series, which are derivatives of 5-substituted-6-halo-A-85380, exhibited a higher binding affinity at α4β2-nAChRs than epibatidine. An anal., by mol. modeling, revealed an important role of the orientation of the addnl. heterocyclic ring on the binding affinity of the ligands with nAChRs. The existing nicotinic pharmacophore models do not accommodate this finding. Two compounds of the series, 6-[18F]fluoro-5-(3-pyridinyl)-A-85380 (I) and 6-chloro-3-[[2-(S)-azetidinyl]methoxy]-5-[(2-[18F]fluoro-5-pyridinyl)pyridine], were radiolabeled with 18F. Comparison of PET data for [18F]-I and 2-[18F]FA shows the influence of lipophilicity on the binding potential. Recent PET studies with [18F]-I demonstrated that its binding potential values in Rhesus monkey brain were ca. 2.5 times those of 2-[18F]FA. Therefore, [18F]35 and several other members of the series, when radiolabeled, will be suitable for quant. imaging of extrathalamic nAChRs.

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Application In Synthesis of Dichloro(1,5-cyclooctadiene)platinum(II). Aromatic compounds can be divided into two categories: single heterocycles and fused heterocycles. Compound: Dichloro(1,5-cyclooctadiene)platinum(II), is researched, Molecular C8H12Cl2Pt, CAS is 12080-32-9, about Synthesis, Coordination and Electrochemistry of a Ferrocenyl-Tagged Aminobisphosphane Ligand. Author is Navratil, Michal; Cisarova, Ivana; Stepnicka, Petr.

Group 10 element diphosphine square planar complexes [FcN(CH2PPh2)2MY2] (Fc = ferrocenyl; M = Ni, Pd, Pt; Y = Cl, Br), Group 11 tetraphosphine tetrahedral complexes [[FcN(CH2PPh2)2]2M]X (M = Cu, Ag, Au; X = BF4, SbF6) and gold binuclear complexes [FcN(CH2PPh2AuCl)2], [FcN(CH2PPh2)2Au]2[SbF6]2 were prepared and examined for their redox activity. Introducing a ferrocene moiety into a mol. results in the incorporation of a metal center and a redox active moiety. The ligand FcN(CH2PPh2)2 (1) was prepared by alkylation of ferrocenamine FcNH2 with hydroxymethylphosphine HOCH2PPh2 and converted to diselenide FcN(CH2P(Se)Ph2)2 (1-Se) for crystallog. identification. Furthermore, a pair of open and cyclic digold(I) complexes containing bis-phosphane 1 as a P,P-bridging ligand, were isolated. Ligand 1, the corresponding phosphane selenide 1-Se and all complexes (except for the poorly soluble [(μ(P,P’)-1)2Au2][SbF6] and unstable [Ag(1-κ2P,P’)2][SbF6]) were further analyzed by cyclic voltammetry.

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Most of the natural products isolated at present are heterocyclic compounds, so heterocyclic compounds occupy an important position in the research of organic chemistry. A compound: 1195-58-0, is researched, SMILESS is N#CC1=CC(C#N)=CN=C1, Molecular C7H3N3Journal, Article, ACS Omega called Thermodynamic Parameters of Elementary Steps for 3,5-Disubstituted 1,4-Dihydropyridines To Release Hydride Anions in Acetonitrile, Author is Zhao, Hui; Li, Yang; Zhu, Xiao-Qing, the main research direction is dihydropyridine hydride ion source thermodn.Computed Properties of C7H3N3.

A series of 3,5-disubstituted 1,4-dihydropyridine derivatives including the derivative with two chiral centers, 6H (R2 = CH3, CH2Ph), as a new type of organic hydride source were synthesized and characterized. The thermodn. driving forces (defined as enthalpy changes or standard redox potentials) of the 6 elementary steps for the organic hydrides to release hydride ions in acetonitrile were measured by isothermal titration calorimeter and electrochem. methods. The impacts of the substituents and functional groups bearing the N1 and C3/C5 positions on the thermodn. driving forces of the 6 elementary steps were examined and analyzed. Moreover, the results showed that the reaction mechanism between the chiral organic hydride and activated ketone (Et benzoylformate) was identified as the concerted hydride transfer pathway based on the thermodn. anal. platform. These valuable and crucial thermodn. parameters will provide a broadly beneficial impact on the applications of 3,5-disubstituted 1,4-dihydropyridine derivatives in organic synthesis and pharmaceutical chem.

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In organic chemistry, atoms other than carbon and hydrogen are generally referred to as heteroatoms. The most common heteroatoms are nitrogen, oxygen and sulfur. Now I present to you an article called Platinum(II) complexes bearing bulky Schiff base ligands anchored onto mesoporous SBA-15 supports as efficient catalysts for hydrosilylation, published in 2019, which mentions a compound: 12080-32-9, mainly applied to silica supported naphthalenolimine Schiff base platinum cyclooctadiene preparation catalyst; bulky Schiff base anchored mesoporous SBA 15 catalyst hydrosilylation; hydrosilylation terminal alkene styrene silane regioselectivity catalyst preparation, Synthetic Route of C8H12Cl2Pt.

Reported herein is an easy-to-prepare novel heterogeneous catalyst of platinum complexes bearing binary ligands of bidentate naphthalenolimine and cyclo-1,5-octadiene that are anchored onto mesoporous silica SBA-15. The presence of the binary ligands not only stabilized the platinum, but also enabled the platinum atoms to form nanoclusters with diameters of ca 1 nm, and led to high platinum loading (8.69 wt%). Moreover, the platinum catalyst exhibited high catalytic activity towards hydrosilylation of terminal alkenes and styrene with silanes under mild and solvent-free conditions, with excellent regioselectivity.

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Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 12080-32-9, is researched, Molecular C8H12Cl2Pt, about Photophysical Properties of Phosphorescent Mono- and Bimetallic Platinum(II) Complexes with C C* Cyclometalating NHC Ligands, the main research direction is imidazopyridinyl bimetallic platinum pyrazolate complex preparation electronic structure phosphorescence; crystal structure imidazopyridine bimetallic platinum pyrazolate complex; mol structure imidazopyridine bimetallic platinum pyrazolate complex; imidazopyridine cyclometalation platinum complex.Reference of Dichloro(1,5-cyclooctadiene)platinum(II).

Due to their square-planar geometry, Pt(II) complexes demonstrate an extraordinary and unique photophys. behavior. The photophys. properties of monometallic Pt(II) complexes depend on the concentration, while in bimetallic Pt(II) complexes they depend on the distance between the metal centers. The authors reveal a correlation between the electronic and photophys. properties of monomeric monometallic Pt(II) complexes and their aggregates with the corresponding bimetallic complexes.

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Heterocyclic compounds can be divided into two categories: alicyclic heterocycles and aromatic heterocycles. Compounds whose heterocycles in the molecular skeleton cannot reflect aromaticity are called alicyclic heterocyclic compounds. Compound: 1195-58-0, is researched, Molecular C7H3N3, about Alkylation of pyridine-3,5-dicarboxamide and pyridine-3,5-dicarbonitriles by radical substitution, the main research direction is alkylation pyridinedicarboxamide pyridinedicarbonitrile; radical substitution pyridinedicarboxamide pyridinedicarbonitrile.Reference of Pyridine-3,5-dicarbonitrile.

Structural modification of NAD(P) model compounds, N,N,N’,N’-tetramethylpyridine-3,5-dicarboxamide (1), pyridine-3,5-dicarbonitrile (2), and 4-methylpyridine-3,5-dicarbonitrile (3), have been explored by the reaction with alkyl radicals such as the 1-adamantyl, tert-Bu, and iso-Pr radicals. The alkyl substitutions of compounds 1, 2, and 3 with the 1-adamantyl and the tert-Bu radical gave both 2-mono and 2,6-disubstitution products, whereas the reaction of compound 2 with the iso-Pr radical gave 2-mono- I, 2,4-di-, 2,6-di-, and 2,4,6-trisubstitution products.

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