Lewis base in the context of Basicity

In chemistry, there are three definitions in common use of the word "base": Arrhenius bases, Brønsted bases, and Lewis bases. All definitions agree that bases are substances that react with acids, as originally proposed by G.-F. Rouelle in the mid-18th century.

In 1884, Svante Arrhenius proposed that a base is a substance which dissociates in aqueous solution to form hydroxide ions OH. These ions can react with hydrogen ions (H according to Arrhenius) from the dissociation of acids to form water in an acid–base reaction. A base was therefore a metal hydroxide such as NaOH or Ca(OH)₂. Such aqueous hydroxide solutions were also described by certain characteristic properties. They are slippery to the touch, can taste bitter and change the color of pH indicators (e.g., turn red litmus paper blue).

Methylmercury is an organometallic cation with the formula [CH₃Hg]. It is the simplest organomercury compound. Methylmercury is extremely toxic, and its derivatives are the major source of organic mercury for humans. It is a bioaccumulative environmental toxicant with a 50-day half-life.Methylmercury (derived biologically from dimethylmercury) is the causative agent of the infamous Minamata disease.

Methylmercury is designated as a "priority hazardous substance" according to the Directive on Environmental Quality Standards (Directive 2013/39/EU).

In chemistry, a nucleophile is a chemical species that forms bonds by donating an electron pair. All molecules and ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are Lewis bases.

Nucleophilic describes the affinity of a nucleophile to bond with positively charged atomic nuclei. Nucleophilicity, sometimes referred to as nucleophile strength, refers to a substance's nucleophilic character and is often used to compare the affinity of atoms. Neutral nucleophilic reactions with solvents such as alcohols and water are named solvolysis. Nucleophiles may take part in nucleophilic substitution, whereby a nucleophile becomes attracted to a full or partial positive charge, and nucleophilic addition. Nucleophilicity is closely related to basicity. The difference between the two is, that basicity is a thermodynamic property (i.e. relates to an equilibrium state), but nucleophilicity is a kinetic property, which relates to rates of certain chemical reactions.

In chemistry, an electron donor is a chemical entity that transfers electrons to another compound. It is a reducing agent that, by virtue of its donating electrons, is itself oxidized in the process. An obsolete definition equated an electron donor and a Lewis base.

In contrast to traditional reducing agents, electron transfer from a donor to an electron acceptor may be only fractional. The electron is not completely transferred, which results in an electron resonance between the donor and acceptor. This leads to the formation of charge transfer complexes, in which the components largely retain their chemical identities. The electron donating power of a donor molecule is measured by its ionization potential, which is the energy required to remove an electron from the highest occupied molecular orbital (HOMO).

A base anhydride is an oxide of a chemical element from group 1 or 2 (the alkali metals and alkaline earth metals, respectively). They are obtained by removing water from the corresponding hydroxide base. If water is added to a base anhydride, a corresponding hydroxide salt can be [re]-formed.

Base anhydrides are Brønsted–Lowry bases because they are proton acceptors. In addition, they are Lewis bases, because they will share an electron pair with some Lewis acids, most notably acidic oxides. They are potent alkalis and will produce alkali burns on skin, because their affinity for water (that is, their affinity for being slaked) makes them react with body water.

Electron-rich is jargon that is used in multiple related meanings with either or both kinetic and thermodynamic implications:

• with regard 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 regard to acid-base reactions, electron-rich species have high pKa's and react with weak Lewis acids.
• with regard 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 faster than in benzene. The electron-donating vs electron-withdrawing influence of various functional groups have been extensively parameterized in linear free energy relationships.
• with regard to Lewis acidity, electron-rich species are strong Lewis bases.

In chemistry, an adduct (from Latin adductus 'drawn toward'; alternatively, a contraction of "addition product") is a product of a direct addition of two or more distinct molecules, resulting in a single reaction product containing all atoms of all components. The resultant is considered a distinct molecular species. Examples include the addition of sodium bisulfite to an aldehyde to give a sulfonate. It can be considered as a single product resulting from the direct combination of different molecules which comprises all atoms of the reactant molecules.

Adducts often form between Lewis acids and Lewis bases. A good example is the formation of adducts between the Lewis acid borane and the oxygen atom in the Lewis bases, tetrahydrofuran (THF): BH₃·O(CH₂)₄ or diethyl ether: BH₃·O(CH₃CH₂)₂. Many Lewis acids and Lewis bases reacting in the gas phase or in non-aqueous solvents to form adducts have been examined in the ECW model. Trimethylborane, trimethyltin chloride and bis(hexafluoroacetylacetonato)copper(II) are examples of Lewis acids that form adducts which exhibit steric effects. For example: trimethyltin chloride, when reacting with diethyl ether, exhibits steric repulsion between the methyl groups on the tin and the ethyl groups on oxygen. But when the Lewis base is tetrahydrofuran, steric repulsion is reduced. The ECW model can provide a measure of these steric effects.