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In chemistry, an electrophile is a chemical species that forms bonds with nucleophiles by accepting an electron pair. [1] Because electrophiles accept electrons, they are Lewis acids . [ 2 ] Most electrophiles are positively charged , have an atom that carries a partial positive charge, or have an atom that does not have an octet of electrons.
Electrostatic potential map of a water molecule, where the oxygen atom has a more negative charge (red) than the positive (blue) hydrogen atoms. Electronegativity, symbolized as χ, is the tendency for an atom of a given chemical element to attract shared electrons (or electron density) when forming a chemical bond. [1]
tert-Butoxide, on the other hand, is a strong base, but a poor nucleophile, because of its three methyl groups hindering its approach to the carbon. Nucleophile strength is also affected by charge and electronegativity : nucleophilicity increases with increasing negative charge and decreasing electronegativity.
The negative oxygen was 'forced' to give electron density to the carbons (because it has a negative charge, it has an extra +I effect). Even when cold and with neutral (and relatively weak) electrophiles, the reaction still occurs rapidly. The phenolate has a negatively charged oxygen.
In chemistry, a nucleophilic substitution (S N) is a class of chemical reactions in which an electron-rich chemical species (known as a nucleophile) replaces a functional group within another electron-deficient molecule (known as the electrophile). The molecule that contains the electrophile and the leaving functional group is called the ...
First, as the energy that is released by adding an electron to an isolated gaseous atom. The second (reverse) definition is that electron affinity is the energy required to remove an electron from a singly charged gaseous negative ion. The latter can be regarded as the ionization energy of the –1 ion or the zeroth ionization energy. [1]
Nevertheless, one can generally examine acid dissociation constants to qualitatively predict or rationalize rate or reactivity trends relating to variation of the leaving group. Consistent with this picture, strong bases such as OH −, OR 2 and NR − 2 tend to make poor leaving groups, due their inability to stabilize a negative charge.
Carbon–fluorine bonds can have a bond dissociation energy (BDE) of up to 130 kcal/mol. [2] The BDE (strength of the bond) of C–F is higher than other carbon–halogen and carbon–hydrogen bonds. For example, the BDEs of the C–X bond within a CH 3 –X molecule is 115, 104.9, 83.7, 72.1, and 57.6 kcal/mol for X = fluorine, hydrogen ...