Activating group
Encyclopedia
In organic chemistry
, a functional group
is called an activating group (or electron donating group) if a benzene
molecule
to which it is attached more readily participates in electrophilic substitution
reactions. Benzene itself will normally undergo substitutions by electrophiles, but additional substituents can alter the reaction rate or products by electronically or sterically affecting the interaction of the two reactants.
Activating groups are generally ortho/para directing for electrophilic aromatic substitution (though the deactivating halogens are also ortho/para directing as they have unshared lone pairs of electrons that are shared with the aromatic ring)
Functional groups are typically divided into three levels of activating ability. Deactivating groups
are assigned to similar groupings.
R = alkyl
Strongly activating substituents favor electrophilic substitution about the ortho and para positions.
This is illustrated by drawing the resonance structures of aniline
: http://s60.photobucket.com/albums/h6/adamboygenius/?action=view¤t=scan0001.jpg
Organic chemistry
Organic chemistry is a subdiscipline within chemistry involving the scientific study of the structure, properties, composition, reactions, and preparation of carbon-based compounds, hydrocarbons, and their derivatives...
, a functional group
Functional group
In organic chemistry, functional groups are specific groups of atoms within molecules that are responsible for the characteristic chemical reactions of those molecules. The same functional group will undergo the same or similar chemical reaction regardless of the size of the molecule it is a part of...
is called an activating group (or electron donating group) if a benzene
Benzene
Benzene is an organic chemical compound. It is composed of 6 carbon atoms in a ring, with 1 hydrogen atom attached to each carbon atom, with the molecular formula C6H6....
molecule
Molecule
A molecule is an electrically neutral group of at least two atoms held together by covalent chemical bonds. Molecules are distinguished from ions by their electrical charge...
to which it is attached more readily participates in electrophilic substitution
Electrophilic substitution
Electrophilic substitution reactions are chemical reactions in which an electrophile displaces a group in a compound, typically but not always hydrogen. Electrophilic aromatic substitution is characteristic of aromatic compounds and is an important way of introducing functional groups onto benzene...
reactions. Benzene itself will normally undergo substitutions by electrophiles, but additional substituents can alter the reaction rate or products by electronically or sterically affecting the interaction of the two reactants.
Activating groups are generally ortho/para directing for electrophilic aromatic substitution (though the deactivating halogens are also ortho/para directing as they have unshared lone pairs of electrons that are shared with the aromatic ring)
Functional groups are typically divided into three levels of activating ability. Deactivating groups
Deactivating groups
In organic chemistry, a deactivating group is a functional group attached to a benzene molecule that removes electron density from the benzene ring, making electrophilic aromatic substitution reactions slower and more complex relative to benzene...
are assigned to similar groupings.
Strongly Activating Groups
- -NNitrogenNitrogen is a chemical element that has the symbol N, atomic number of 7 and atomic mass 14.00674 u. Elemental nitrogen is a colorless, odorless, tasteless, and mostly inert diatomic gas at standard conditions, constituting 78.08% by volume of Earth's atmosphere...
HHydrogenHydrogen is the chemical element with atomic number 1. It is represented by the symbol H. With an average atomic weight of , hydrogen is the lightest and most abundant chemical element, constituting roughly 75% of the Universe's chemical elemental mass. Stars in the main sequence are mainly...
2 -NHR -NR2
- -OOxygenOxygen is the element with atomic number 8 and represented by the symbol O. Its name derives from the Greek roots ὀξύς and -γενής , because at the time of naming, it was mistakenly thought that all acids required oxygen in their composition...
H -O-
R = alkyl
Strongly activating substituents favor electrophilic substitution about the ortho and para positions.
This is illustrated by drawing the resonance structures of aniline
Aniline
Aniline, phenylamine or aminobenzene is an organic compound with the formula C6H5NH2. Consisting of a phenyl group attached to an amino group, aniline is the prototypical aromatic amine. Being a precursor to many industrial chemicals, its main use is in the manufacture of precursors to polyurethane...
: http://s60.photobucket.com/albums/h6/adamboygenius/?action=view¤t=scan0001.jpg
Weakly Activating Groups
- -CH3 -C2H5 -R
- -C6H5