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A nucleophile is a chemical species that donates an electron pair to an electrophile to form a chemical bond in relation to a reaction. All molecules or ions with a free pair of electrons or at least one pi bond can act as nucleophiles. Because nucleophiles donate electrons, they are by definition Lewis bases. Nucleophilicity refers to a substance's nucleophilic character and is often used to compare the affinity of atoms.
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Many schemes attempting to quantify relative nucleophilic strength have been devised. The more basic the ion (the higher the pKa of the conjugate acid) the more reactive it is as a nucleophile. In a given group, polarizability is more important in the determination of the Nucleophilicity, The easier it is to distort the electron cloud around an atom or molecule the more readily it will react.
In nucleophilic reactions, the size of the nucleophile can be an important (steric) factor. Smaller is more effective. Thus, although the nucleophilic atom in the two species below is the same (oxygen) and they have similar structures, methoxide ion is a more effective nucleophile than t-butoxide ion, even though they are about equally effective as bases. The larger t-butoxide ion has more difficulty reaching an electrophilic center, which is typically a carbon buried at the core of the molecular structure. That is not a problem when it acts as a base because acidic protons usually lie in the periphery of the molecule and are easily accessible.
The most common type of nucleophiles are those containing atoms with unshared electron pairs. A negatively charged species is usually a stronger nucleophile or base than its neutral analog. Thus, hydroxide ion is stronger, both as a base and as a nucleophile, than water. Carbon bonded to a metal has strong negative character, revealed when writing resonance structures. The carbon atom in such molecules is considered a strong nucleophile. Recall the structures of n-butyllithium and Grignard (organomagnesium) reagents from previous notes. The pi bond is a region of high electron density. Pi bonds are not as strong as sigma bonds, which means that pi electrons are more available for reactions because pi bonds are more easily broken. Molecules containing pi bonds are considered weak nucleophiles or bases, because they can react with strong acids or electrophiles. Periodic trends in nucleophilicity are such that, other factors being similar, nucleophilicity increases from right to left across the same row, and from top to bottom across the same period or group. This trend is different from the basicity trend, which increases in the same way across a row, but from bottom to top within a period.
The market for nucleophilic substances is expected to grow at a significant rate. Global Market is expected to reach USD 2.56 Billion by 2022. Constant technological advancements pertaining to the development of nucleophiles which can be used to boost usage rates over the forecast period.
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