Structure of 4,4'-Bipyridine

 4,4'-Bipyridine is used in transition-metal complex catalyst chemistry for uniform polymerization, luminescence chemistry, and in spectrophotometric analysis. It plays an important role as a photosensitizer and luminescent material. It is also used as a precursor to paraquat viz. N,N'-dimethyl-4,4'-bipyridinium.

This Thermo Scientific brand product was originally part of the Alfa Aesar product portfolio. Some documentation and label information may refer to the legacy brand. The original Alfa Aesar product/item code or SKU reference has not changed as a part of the brand transition to Thermo Scientific.

Applications

4,4′-Bipyridine is used in transition-metal complex catalyst chemistry for uniform polymerization, luminescence chemistry, and in spectrophotometric analysis. It plays an important role as a photosensitizer and luminescent material. It is also used as a precursor to paraquat viz. N, N′-dimethyl-4,4′-bipyridinium.

Chemical Structure Description

A chemical structure of a molecule includes the arrangement of atoms and the chemical bonds that hold the atoms together. The 4,4'-Bipyridine molecule contains a total of 21 bond(s) There are 13 non-H bond(s), 12 multiple bond(s), 1 rotatable bond(s), 12 aromatic bond(s), 2 six-membered ring(s) and 2 Pyridine(s).

Images of the chemical structure of 4,4'-Bipyridine are given below:

2-dimensional (2D) chemical structure image of 4,4'-Bipyridine

 

3-dimensional (3D) chemical structure image of 4,4'-Bipyridine

The 2D chemical structure image of 4,4'-Bipyridine is also called the skeletal formula, which is the standard notation for organic molecules. The carbon atoms in the chemical structure of 4,4'-Bipyridine are implied to be located at the corner(s) and hydrogen atoms attached to carbon atoms are not indicated – each carbon atom is considered to be associated with enough hydrogen atoms to provide the carbon atom with four bonds.

The 3D chemical structure image of 4,4'-Bipyridine is based on the ball-and-stick model which displays both the three-dimensional position of the atoms and the bonds between them. The radius of the spheres is, therefore, smaller than the rod lengths in order to provide a clearer view of the atoms and bonds throughout the chemical structure model of 4,4'-Bipyridine.

The 4,4'-Bipyridine molecule shown in the visualization screen can be rotated interactively by keep clicking and moving the mouse button. Mouse wheel zoom is available as well – the size of the 4,4'-Bipyridine molecule can be increased or decreased by scrolling the mouse wheel.

The information of the atoms, bonds, connectivity, and coordinates included in the chemical structure of 4,4'-Bipyridine can easily be identified by this visualization. By right-clicking the visualization screen, various other options are available including the visualization of van der Waals surface and exporting to an image file.

Sodium amide

 Sodium amide, normally known as sodamide, is the chemical compound with the formulation NaNH2. This solid, that's dangerously reactive towards the water, is white while pure, however, industrial samples are generally grey because of the presence of small portions of metal iron from the production process. Such impurities do now no longer commonly have an effect on the software of the reagent. NaNH2 has been broadly hired as a robust base in natural synthesis.

Sodium Amide is mainly used as a strong base in organic chemistry, often in liquid ammonia solution. Sodium amide decomposes explosively in contact with water.

Preparation and structure

Sodium amide may be organized through the response of sodium with ammonia gas, however, additionally, it is organized through the response in liquid ammonia with the usage of iron(III) nitrate as a catalyst. The response is quickest on the boiling factor of the ammonia, ca. -33 °C.

2 Na + 2 NH3 → 2 NaNH2 + H2

NaNH2 is a salt-like cloth and as such, crystallizes as a limitless polymer. The geometry of sodium is tetrahedral.[4] In ammonia, NaNH2 bureaucracy conductive solutions, regular with the presence of Na(NH3)6+ and NH2- anions.

Uses

Sodium amide is used withinside the business manufacturing of indigo, hydrazine, and sodium cyanide. It is the reagent of desire for the drying of ammonia (liquid or gaseous) and is likewise broadly used as a robust base in natural chemistry, regularly in liquid ammonia solution. One of the primary benefits of the usage of sodamide is that it's far an extremely good base and infrequently serves as a nucleophile. It is but poorly soluble and its use has been outmoded through associated reagents together with sodium hydride, sodium bis(trimethylsilyl)amide (NaHMDS), and lithium diisopropylamide (LDA).

Preparation of alkynes

Sodium amide induces the lack of molecules of hydrogen bromide from a vicinal dibromoalkane to provide a carbon-carbon triple bond, as withinside the guidance of phenylacetylene below.

Hydrogen chloride and/or ethanol also can be removed in this way, as withinside the guidance of 1-ethoxy-1-butyne.

Cyclization reactions

Where there's no β-hydrogen to be removed, cyclic compounds can be formed, as withinside the guidance of methylenecyclopropane below.

2-Amino-6-methylpyridine based co-crystal salt formation using succinic acid

 The current work reports the formation methodology of the co-crystal between 2-amino-6-methylpyridine and succinic acid, its single-crystal characterization, and the computational study. The single-crystal analysis showed that the co-crystal molecules are interlinked by N···H−O and O···H−O bonds to form the R22 (8) loop and D22 (5) and D22 (8) finite pattern along with the formation of the infinite 2D network in the (1 0 1 bar) plane having base vectors [1 0 1] and [0 1 bar 0]. Moreover, the weak interactions of the π-π stacking type and Csbnd O-Cg interactions are found in the title compound helping further strengthen the crystal structure. 

The Hirshfeld surface analysis confirmed that H···H interatomic contacts are the most significant contributor to entire interatomic contacts with a contribution of 45.8%. 

The computational studies supported the presence of significantly strong hydrogen bonds within the title complex. The molecular orbital analysis suggested that both HOMO/HOMO-1 and LUMO/LUMO+1 could participate in the complex's oxidative-reductive processes.

The HOMO has dominating contributions from one succinate unit and minor contributions from the H-bonded NH2-group of the neighboring 2-amino-6-methyl pyridine-1-ium moiety. The calculated values of the global reactivity parameters suggest noticeable stability of the title complex. It was also shown to possess quite pronounced nonlinear optical properties.

Highlights

•Effective production of the novel 2-amino-6-methylpyridine co-crystal salt.

•Salt stabilization by ionic interactions, hydrogen bonds, and stacking interactions.

•DFT study supports the existence of quite strong intracomplex hydrogen bonding.

•Current compounds can have potential future applications in pharmacology.

Formula: C6H8N2

Molecular weight: 108.1411

IUPAC Standard InChI: InChI=1S/C6H8N2/c1-5-3-2-4-6(7)8-5/h2-4H,1H3,(H2,7,8) Copy

InChI version 1.06

IUPAC Standard InChIKey: QUXLCYFNVNNRBE-UHFFFAOYSA-N Copy

CAS Registry Number: 1824-81-3

Chemical structure: C6H8N2

This structure is also available as a 2d Mol file or as a computed 3d SD file

The 3d structure may be viewed using Java or Javascript.

Other names: 2-Picoline, 6-amino-; 2-Amino-6-methylpyridine; 2-Amino-6-picoline; 6-Amino-2-methylpyridine; 6-Amino-2-picoline; 6-Methyl-2-pyridinamine; 6-Methyl-2-pyridylamine; Pyridine, 2-amino-6-methyl-; 6-Methyl-2-aminopyridine; NSC 1488; NSC 6971

Reagent Friday: Sodium Amide (NaNH2)

 

NaNH2 (Sodium amide) 

 What it’s used for: NaNH2 is a strong base. In the rare cases when its strong basicity doesn’t cause side reactions, it can be an excellent nucleophile  It’s used for deprotonation of weak acids and also for elimination reactions.

The NH2- anion is the conjugate base of ammonia (NH3). If you’ll recall, the weaker the acid, the stronger the conjugate base – and since NH3 has a pKa of 38, NH2 is a strong base indeed. (Note that although I’m talking about NaNH2 here, the bases LiNH2 and KNH2 essentially behave the same way.)

As a strong base, NaNH2 will deprotonate alkynes, alcohols, and a host of other functional groups with acidic protons such as esters and ketones.

As a base, it’s often used in situations where a strong, small base is required. Like a piranha, NaNH2 is small, fast, has razor-sharp teeth, and can find its way into tight, enclosed spaces.

Mechanism Of NaNH2: Double Elimination To Give Alkynes

How it works.

Deprotonation of functional groups such as OH and even alkyne C-H should hopefully be straightforward, but the use of bases to make alkenes may require some explanation. This is what is known as an elimination reaction, in that the elements H and Br (in this example) are removed in order to form the alkene. Specifically, this is an example of an E2 reaction. 

Since the alkene still has a halide attached, this too can be removed to generate a second double bond (π bond). This is another example of the E2 in that the hydrogen has to be anti to the bromine that is eliminated, but is unusual in that it is sp2 hydrogen that is affected here:

A note of caution on the use of NaNH2 as a nucleophile. My trusty copy of March has the following to say:

“The conjugate base of ammonia  is sometimes used as a nucleophile, but in most cases offers no advantage over ammonia, since the latter is basic enough.”

Furthermore, since NaNH2 is a strong base, it has the significant disadvantage of promoting side reactions from elimination (this can occur when attempting an SN2 with NaNH2 as the nucleophile, for example). Therefore, it is generally wise to avoid using NaNH2 as a nucleophile in organic synthesis. Sodium azide (followed by reduction) is the usual substitute.

I suppose one could use NaNH2 as a nucleophile in a case like this one (below) but again it offers no significant advantage over NH3:

Complications from Dual Roles of Sodium Hydride as a Base and as a Reducing Agent

 Sodium hydride is a not unusualplace reagent for substrate activation in nucleophilic substitution reactions. Sodium hydride can behave each as a base and as a supply of hydride. This twin capacity withinside the presence of an electrophile which includes benzyl bromide affects withinside the formation of byproducts while dimethylformamide or acetonitrile are used as solvents for those reactions. The structural nature of those byproducts is found in this record.

Sodium hydride is a generally used base for deprotonation of alcohols, phenols, amides, ketones, esters, and different useful corporations for advertising in their nucleophilic substitution.1 Typically, sodium hydride and the reagents are jumbled in polar aprotic solvents which include DMSO, DMF, or acetonitrile for those SN2-kind reactions. Whereas the literature is replete with examples of using those solvents in such reactions, our hazard discovery of reactivity of sodium hydride with those generally used solvents, DMF and acetonitrile, suggests that sure undesired aspect reactions concerning those solvents are probably not unusualplace, however unrecognized. As is disclosed on this record, the foundation reason for those complicating aspect-reactions is the twin position that sodium hydride is famous as a base and as a supply of hydride.

The form of byproducts on the way to be disclosed on this record are usually hard to stumble on with not unusualplace visualization techniques and are smooth to overlook. Using benzyl bromide because the electrophile helped us to isolate the byproducts through UV detection and the systems had been at the end assigned through X-ray evaluation of unmarried crystals.

During benzylation of compound 1 withinside the presence of NaH and benzyl bromide in DMF, we diagnosed an uncommon stable byproduct. The 1H NMR spectrum of this byproduct becomes simple and becomes without resonances originating from the glucal substrate. Assignment of shape becomes achieved through X-ray evaluation. This compound crystallized withinside the monoclinic area institution P21/c. Once in hand, the X-ray shape amazed us, because it confirmed that the stable, compound 3, become a by-product of dimethylamine. At the beginning of the dimethylamine, moiety becomes absolutely DMF, which is served because of the solvent for the response. We are aware that DMF becomes freshly distilled earlier to apply withinside the response and that there has been no hint of dimethylamine in DMF as discerned through a poor ninhydrin assay.

Sodium Ethoxide Preparation and Formula

 Sodium ethoxide, additionally called sodium to ethylate, is the natural compound with the formulation C2H5ONa, or NaOEt. It is a white strong, even though impure samples seem yellow or brown. It dissolves in polar solvents including ethanol. It is typically used as a robust base

Chemical Formula

The chemical formulation for Sodium ethoxide is C2H5ONA.

Here is a study of the distribution of ions in Sodium Ethoxide. The left picture is the ball and stick version of the ethoxide anion whilst the only the proper is that of sodium cation.

Sodium ethoxide Preparation

Synthesis of Sodium ethoxide may be accomplished with the aid of using chemically reacting sodium hydroxide or sodium steel with ethyl alcohol. This allows for the creation of Sodium ethoxide in a liquid shape.

2 C2H5OH + 2 Na → 2 C2H5ONa + H2

A response among sodium hydroxide and anhydrous ethanol offers us Sodium ethoxide mixed with water. We can then take away the water with the aid of using the use of a drying agent and it's going to go away with Sodium ethoxide having extra purity.

C2H5OH + NaOH ⇌ C2H5ONa + H2O

The strong or powdered shape of Sodium ethoxide is yellow in color.

Sodium ethoxide in Ethanol

When sodium is introduced to ethanol, the chemical response produces hydrogen GAS which paperwork bubbles and leaves a sodium ethoxide answer. Sodium ethoxide is a shape of an alkoxide. The answer of sodium ethoxide in ethanol is colorless. Sodium ethoxide while introduced to water reacts to shape ethyl alcohol or ethanol.

Sodium ethoxide Boiling Point

The boiling factor of Sodium ethoxide is ninety-one ranges Celsius.

Sodium ethoxide MSDS

Sodium ethoxide is unsafe for human fitness if it comes in touch with the pores and skin and eyes. Exposure of the pores and skin to this chemical can deliver an upward push to blisters and inflammations. The chemical, in touch with the eyes, might also result in blindness. Inhaling or eating this chemical compound would possibly bring about critical fitness troubles like

Damage to the mucous membranes

• Irritation of breathing and gastrointestinal tracts
• Choking
• Unconsciousness
• Lung damage
• In intense cases, it is able to additionally result in death.

In case there may be a touch of this chemical with the bodily body, ok care has to be taken to keep away from any critical fitness troubles. If the eyes are available touch with sodium ethoxide, the eyes have to be washed fastidiously with smooth water for numerous mins and a physician is to be consulted simply to be on the secure side.

The equal holds real for any pores and skin touch. Skin ointments have to be used to assuage the pores and skin from chemical burns and inflammations.

Inhaling those chemical fumes would possibly reason critical respiration troubles. The patient, in this case, has to be straight away taken to a sector of sparkling air, and tight garments if any have to be loosened. Artificial respiratory and oxygen is probably vital for buying lower back to everyday respiration.

Sodium ethoxide is a strong chemical compound. However, it's far especially volatile and could react violently if it comes in touch with acids, water or moisture, chlorinated solvents, air, dirt, and light. Sodium ethoxide is especially flammable. It is a hygroscopic chemical compound, which means that it's far touchy to air, moisture, or light. It is consequently really useful to preserve Sodium ethoxide far from open flames or something that would reason sparks and reasons the chemical to trap hearthplace. In case there may be a hearth place, dry chemical powders can be used to extinguish small fires and a sprig for a big hearth place.

Sodium ethoxide would possibly trap hearthplace if it comes in touch with air. So it has to be saved in a dry, tight, airless box and saved in a fab place.

Special sodium ethoxide protection measures are had to comply with whilst handling this chemical. While coping with this chemical, unique safety equipment like splash goggles, vapor/dirt respirator, gloves, suit, etc. have to be used with the purpose to make a certain absence of direct exposure.

Sodium ethoxide is classed as Hazard Class 4.2.

While disposing of wastes of sodium ethoxide, has to be accomplished in methods that might be according to state, federal, and neighborhood environmental rules to keep away from ability unsafe conditions.

Sodium Hydride (Properties, Uses)

 In oil, sodium hydride is a silvery to whitish powder or slurry. It is the chemical compound with the empirical formula NaH. This alkali metal hydride is largely utilized in organic synthesis as a powerful but flammable base. In contrast to molecular hydrides such as borane, methane, ammonia, and water, NaH is a saline (salt-like) hydride made up of Na+ and H− ions. Ionic crystals, salt compositions in which the hydrogen is negative monovalent ions, include sodium hydride.

When heated, NaH decomposes without melting, and sodium hydride is hydrolyzed with water to produce sodium hydroxide and hydrogen. It’s an ionic substance that’s insoluble in organic solvents (yet soluble in molten Na), indicating that there are no H- ions in the solution. Because of NaH’s insolubility, all reactions involving it takes place at the solid’s surface. Pure sodium hydride is silver needle-like crystals, but commercially available sodium hydride commerce is usually a mild gray crystalline powder with a 25 percent to 50 percent sodium hydride concentration dispersed in oil. The relative density is 0.92.

The direct interaction of hydrogen and liquid sodium Hyderide produces NaH. Although pure NaH is colorless, samples usually seem grey. NaH (0.968 g/cm3) is about 40% denser than Na. Sodium hydride has a crystalline rock salt structure (lattice constant a = 0.488nm), and hydrogen ion exists in anion form as lithium hydride in ionic crystalline. It decomposes explosively in water; reacts violently with lower alcohols; dissolves in molten sodium and molten sodium hydroxide; insoluble in liquid ammonia, benzene, carbon tetrachloride, and carbon disulfide; has a heat of production of 69.5kJ mol-1; and decomposes into metallic sodium and hydrogen at a high temperature of 800 °C.