Electron Releasing Group
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Electron Releasing Group
Electron-rich is jargon that is used in multiple related meanings with either or both kinetic and thermodynamic implications: * with regards to electron-transfer, electron-rich species have low ionization energy and/or are reducing agents. Tetrakis(dimethylamino)ethylene is an electron-rich alkene because, unlike ethylene, it forms isolable radical cation. In contrast, electron-poor alkene tetracyanoethylene is an electron acceptor, forming isolable anions. * with regards to acid-base reactions, electron-rich species have high pKa's and react with weak Lewis acids. * with regards to nucleophilic substitution reactions, electron-rich species are relatively strong nucleophiles, as judged by rates of attack by electrophiles. For example, compared to benzene, pyrrole is more rapidly attacked by electrophiles. Pyrrole is therefore considered to be an electron-rich aromatic ring. Similarly, benzene derivatives with electron-donating groups (EDGs) are attacked by electrophiles faste ...
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Electron-transfer
Electron transfer (ET) occurs when an electron relocates from an atom, ion, or molecule, to another such chemical entity. ET describes the mechanism by which electrons are transferred in redox reactions. Electrochemical processes are ET reactions. ET reactions are relevant to photosynthesis and respiration and commonly involve transition metal complexes. In organic chemistry ET is a step in some industrial polymerization reactions. It is foundational to photoredox catalysis. Classes of electron transfer Inner-sphere electron transfer In inner-sphere ET, two redox centers are covalently linked during the ET. This bridge can be permanent, in which case the electron transfer event is termed intramolecular electron transfer. More commonly, however, the covalent linkage is transitory, forming just prior to the ET and then disconnecting following the ET event. In such cases, the electron transfer is termed intermolecular electron transfer. A famous example of an inner sphere ET proces ...
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Ionization Energy
In physics and chemistry, ionization energy (IE) is the minimum energy required to remove the most loosely bound electron of an isolated gaseous atom, Ion, positive ion, or molecule. The first ionization energy is quantitatively expressed as :X(g) + energy ⟶ X+(g) + e− where X is any atom or molecule, X+ is the resultant ion when the original atom was stripped of a single electron, and e− is the removed electron. Ionization energy is positive for neutral atoms, meaning that the ionization is an endothermic process. Roughly speaking, the closer the outermost electrons are to the atomic nucleus, nucleus of the atom, the higher the atom's ionization energy. In physics, ionization energy (IE) is usually expressed in electronvolts (eV) or joules (J). In chemistry, it is expressed as the energy to ionize a Mole (unit), mole of atoms or molecules, usually as Joule per mole, kilojoules per mole (kJ/mol) or Kilocalorie per mole, kilocalories per mole (kcal/mol). Comparison of ion ...
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Oxidation Potential
Redox potential (also known as oxidation / reduction potential, ''ORP'', ''pe'', ''E_'', or E_) is a measure of the tendency of a chemical species to acquire electrons from or lose electrons to an electrode and thereby be reduced or oxidised respectively. Redox potential is expressed in volts (V). Each species has its own intrinsic redox potential; for example, the more positive the reduction potential (reduction potential is more often used due to general formalism in electrochemistry), the greater the species' affinity for electrons and tendency to be reduced. Measurement and interpretation In aqueous solutions, redox potential is a measure of the tendency of the solution to either gain or lose electrons in a reaction. A solution with a higher (more positive) reduction potential than some other molecule will have a tendency to gain electrons from this molecule (i.e. to be reduced by oxidizing this other molecule) and a solution with a lower (more negative) reduction potential w ...
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Tetrakis(dimethylamino)ethylene
Tetrakis(dimethylamino)ethylene (TDAE) is an organic compound with the formula , It is a colorless liquid. It is classified as an enamine. Primary and secondary enamines tend to isomerize, but tertiary enamines are kinetically stable. One unusual feature of TDAE is that it is a tetra-enamine. The pi-donating tendency of the amine groups strongly enhances the basicity of the molecule, which does exhibit properties of a typical alkene. Reactions TDAE reacts with oxygen in a chemiluminescent reaction to give tetramethylurea. The initial intermediate is (2+2) adduct, a 1,2-dioxetane. This species decomposes to electronically excited tetramethylurea. This returns to the ground state is accompanied by emission of green light with a maximum at 515 nm. TDAE is an electron donor with E = 1.06 V vs Fc+/0. TDAE has been examined as a reductant in coupling reactions. As one of many of examples of its redox behavior forms a charge-transfer salt with buckminsterfullerene: :C2(N(CH3 ...
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Ethylene
Ethylene (IUPAC name: ethene) is a hydrocarbon which has the formula or . It is a colourless, flammable gas with a faint "sweet and musky" odour when pure. It is the simplest alkene (a hydrocarbon with carbon–carbon bond, carbon–carbon double bonds). Ethylene is widely used in the chemical industry, and its worldwide production (over 150 million tonnes in 2016) exceeds that of any other organic compound. Much of this production goes toward creating polyethylene, which is a widely used plastic containing polymer chains of ethylene units in various chain lengths. Production greenhouse gas emissions, emits greenhouse gases, including methane from feedstock production and carbon dioxide from any non-sustainable energy used. Ethylene is also an important natural plant hormone and is used in agriculture to induce ripening of fruits. The hydrate of ethylene is ethanol. Structure and properties This hydrocarbon has four hydrogen atoms bound to a pair of carbon atoms that are con ...
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Radical Cation
Radical cations are denoted M^. Salts of these species have been isolated in the cases of dibenzocyclooctatetraene, various tertiary amines, and some polymethylated derivatives of azulene. Radical cations, like radical anions, have one unpaired electron, i.e. they are paramagnetic. Mass spectrometry Radical cations appear prominently in mass spectrometry. When a gas-phase molecule is subjected to electron ionization one electron is abstracted by an electron in the electron beam to create a radical cation M+.. This species represents the molecular ion or parent ion. A typical mass spectrum shows multiple signals because the molecular ion fragments into a complex mixture of ions and uncharged radical species. For example, the methanol radical cation fragments into a methenium cation and a hydroxyl radical. In naphthalene the unfragmented radical cation is by far the most prominent peak in the mass spectrum. Secondary species are generated from proton gain (M+1) and proton loss ...
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