Introduction

The physical properties of a compound mainly depend on the type of

links that hold the atoms of a molecule together. These can indicate the
type of structure and predict its physical properties. Next, the following will be given to
to know the theory of resonance, which is nothing more than the accumulation of the
knowledge that one has about physical and chemical properties and
spectroscopic of millions of organic compounds.

In addition to the inductive effect, which is known as the effect of a substituent.

due to the permanent polarization of a bond; that is, if in a molecule
it establishes a dipole, its action is transmitted through the carbon chain.

Inductive effect

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 It is the one that prevails in the normal state of the molecule. It is a phenomenon associated
essentially to simple covalent bonds. The electronic pair (:), which is the bond
covalent bond, shifts slightly when there is an atom in the molecule that
exerts a greater or lesser attraction on the electronic pair than the rest of the
atoms.
The inductive effect is then, the effect of a substituent due to the
permanent polarization of a bond; that is, if a dipole is established in a molecule,
its action is transmitted through the carbon chain. It is represented with a date
whose tip is directed towards the most electronegative atom.

The inductive effect is the displacement of electric charge in a bond.

simple towards the atom or the most electronegative group of the molecule.
Depending on whether there is a transfer or attraction of electric charge, the inductive effect is
It is called +I or -I and it is determined by the functional group or type of molecule.
for example, the alkyl groups increase the +I effect (donation) the more carbon atoms there are.
having, that is to say, the more carbons, the greater the capacity to give up the load will increase
electric a atoms o groups more electronegative.
The following figure shows the different atoms and groups arranged according to
its ability to transfer or attract electric charge, or in other words, its effect
inductive.

It can be seen that those more electronegative groups (capable of attracting

electric charge) are those that have the greatest inductive effect -I, while those that
to yield the electrons son the what they have effect +I.
The inductive effect is very important as it helps to understand how they will
organic reactions occur according to the charge density present in the
molecules and therefore know if they will be attacked by electrophiles or nucleophiles.
The inductive effect allows us to compare the acidity of different compounds.
organic.

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Influence of the inductive effect on acidity and
basicity of compounds

Comparing the acidity of a carboxylic acid with its corresponding acids

replaced we determined the influence of the inductive effect on acidity. The property
characteristic chemistry of carboxylic acids in acidity according to Bronsted-Lowry,
they are acidic because each carboxylic group (due to the present OH- group) has the
ability to donate a proton (hydrogen nucleus) in an acid-base exchange.
In an aqueous solution of any carboxylic acid, water acts as a receptor.
of proton, that is to say as a base, establishing an equilibrium between organic acid,
water, carboxylate ion and hydronium ion:

R—COOH + H2O R—COO- + H3O+

Acid Base

The extent to which this reaction produces ions is determined by the degree of acidity.
from the acid. With stronger acids, there is a higher concentration of ions in equilibrium.

The equilibrium constant (ionization or acidity) for the previous reaction Ka, given by
the expression:

Ka = [R—COO-] x [H3O+]
[R—COOH]

It serves as a measure of the strength of the acid; the greater the magnitude of Ka, the stronger the acid.

the acid is strong.

CCl3—COOH> CHCl2 —COOH> CH2Cl —COOH> CH3 -COOH

The presence of the substituents (Chlorine) causes a shift in the

electronic density towards the neighborhood, with the consequent decrease in density
electronics in the carboxyl group —COOH. This is the reason why the atom of
hydrogen —COOH remained looser and, for this reason, the attraction force that
the polar solvent (water) acting on that hydrogen atom produces a greater

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dissociation.

Ethanoic CH3 -COOH Ka= 1.75 x 10-5

Monochloroacetic acid CH2Cl -COOH Ka= 136 x 10-5
Dichloroacetic Dichloromethane
--COOH Ka= 5530 x 10-5
Trichloroacetic CCl3 —COOH Ka= 23200 x 10-5

Now, if we move the inductive substituent away from the —COOH group, it is logical to think that the
inductive effect will be weaker as the substituent moves away from the group —
Induced COOH.

Example:
Butanoic CH3 -CH2 -CH2 —COOH Ka= 1.52 x 10-5
4 chloro-butanoic CH2Cl -CH2 -CH2 —COOH Ka= 2.96 x10-5
3 cloro-Butanoico CH3 -CHCl -CH2 —COOH Ka= 8,9 x 10-5
2-chloro-Butanoic acid CH3 -CH2 -CHCl —COOH Ka= 139 x 10-5
This effect is closely related to the electronegativity of the elements.
for this reason, alpha-fluoroacetic acid is more acidic than alpha-iodoacetic acid.

Example:
FCH2 —COOH Ka= 260 x 10-5
ClCH2 —COOH Ka= 136 x 10-5
BrCH2 —COOH Ka= 125 x 10^-5
ICH2 —COOH Ka= 67 x 10-5

Basicity:

This effect also influences alkalinity: According to Bronsted-Lowry, a base

it is a proton receptor. In an aqueous solution of ammonia, water acts as
a proton donor, that is, like an acid, this proton is accepted by ammonia,
acting accordingly as a basis, establishing a balance between
ammonia, water, ammonium ion and hydroxide ion

NH3 + H2O ⇌ NH4+ + OH-

Acid-base base
Kb= [R —NH3+] x [OH-]
Ammonia

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We say that amines (R —NH2; R2 —NH; R3 N) have basic character because in
accusatory solution, both primary and secondary, act like ammonia.

R—NH2 + H2O → R—NH3 + OH−CH3

The presence of the —CH3 group, an electron donor, increases the electron density.
from nitrogen (N= 3.0) which makes it more suitable to accept more protons in
primary amines and even more so in secondary amines, but as the increase of the
Basicity depends, in addition to the electronic density of hydrogen, on solvation.
from the amine by the water, it certainly results that dimethylamine is more basic than the
methylamine and that trimethylamine (which should be the most basic of the three, due to
inductive effect), it is the least basic because the inductive effect is countered by
the difficulty of solvating, as it does not have any hydrogen bonded to the nitrogen atom.

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 Resonance
Resonance is a linking system between the atoms of a molecule that,
due to the complex distribution of its electrons, it achieves greater stability than
with a simple link. This distribution of electrons does not fluctuate, contrary to what its
The name makes one think. Numerous organic compounds exhibit resonance, as in
the case of thearomatic compounds.

Examples of substituents -R/-M:acetyl- nitrile- nitro

Examples of +R/+M substituents:alcohol- amina

Molecular resonance is a key component in the theory oflink

covalentFor its existence, the presence of double or triple bonds is essential.
in the molecule. The net flow of electrons from or towards the substituent is
determined also by theinductive effectThe mesomeric effect as a result
of the overlap oforbitalp(resonance) has no effect on this inductive effect,
since the inductive effect is exclusively related to the
electronegativityof the atoms, and their structural chemistry (which atoms are
connected to which ones).
Numerous organic compounds exhibit resonance, as in the case of
thearomatic compounds.

Examples

Scheme 2. Examples of resonance in the molecule ofozone, benzeneand the cation

of thealilo group.
The resonance of ozoneit is represented by two resonant structures in the
top part of Scheme 2. In fact, the two terminal oxygen atoms are
equivalents and form a hybrid structure that is represented on the right with -1/2
indicating that the charge is distributed between the two oxygen atoms and the double bonds
partials.

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 The concept of benzene as a hybrid of two conventional structures
(medium in the scheme 2) was one of the important milestones in chemistry devised
forKekulé, de tal forma que las dos formas del anillo que representan la resonancia
The total of the system is often referred to as Kekulé structures. In the hybrid structure
to the right, the circle replaces the three double links of thebenzene.
Thecationof theGrupo alilo (lower part of scheme 2) has two forms
resonant through the double bond that causes the positive charge to be delocalized
throughout the entire cation of the allyl group.
Some organic molecules can be represented by two or more
Lewis structures, which differ from each other only in the distribution of the
electrons, which are referred to as resonant structures. In these cases, the molecule
it will have characteristics of both structures and it is said that the molecule is a hybrid
of resonance of resonant structures. The resonance method allows
to know, in a qualitative way, the stabilization that a molecule can achieve by
electronic delocalization. The greater the number of resonant structures
The greater the ability to describe a chemical species, the greater its stability.

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 Resonance Structures
The Lewis Structure is a graphical representation that shows the bonds.
entre los átomos de una molécula y los pares de electrones solitarios que puedan
exist; it can be used to represent molecules formed by the union of their
atoms through covalent bonding. The Lewis structure was proposed by Gilbert
Lewis, who introduced it for the first time in 1915.

Lewis structures show the different atoms of a given

molecule using its chemical symbol and lines that are drawn between the atoms that are joined
between each other. Sometimes, pairs of points are used to represent each link instead.
of lines. The unpaired electrons are represented by a line or with a pair
of points, and are placed around the atoms to which they belong.

For some molecules and ions, it is difficult to determine which lone pairs.
they must be moved to form double or triple bonds. That is, sometimes, the
case when multiple atoms of the same type surround the central atom.

When this occurs, the Lewis structure for the molecule is a structure
of resonance, and the molecule exists as a resonance hybrid. The structures of
resonance is the different structures of the same molecule due to the
delocalization of electrons, the most common example is benzene, ozone and the
ethylene; the more structures the molecule has, the more stable it is and the harder it is that
react why the electrons they are less available.
Each of the different possibilities overlaps with the others, and is considered
that the molecule has a Lewis structure equivalent to the average of these
states.

When comparing the resonance structures for the same molecule,

usually those with the least formal burden contribute more to the total hybrid of the
resonance. When formal charges are necessary, resonance structures
that have negative charges in the most electronegative elements and positive charges
the less electronegative elements are favored.

Structures of Resonance
Link system between the atoms of a molecule that, due to the complex
the distribution of its electrons, achieves greater stability than with a bond
simple. This distribution of electrons does not fluctuate, contrary to what its name suggests.
thinking. Numerous organic compounds exhibit resonance, as in the case of the

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compounds aromatic.

Resonance structures exist only on paper. They do not exist as such.

Resonance structures are useful because they allow the representation of molecules, ions, and
radicals for which a single Lewis structure is inadequate. They are written
so two or more of these structures are called resonance structures or
resonance contributors. The structures are connected with a double-headed arrow
(↔), and it is said that the real molecule, radical, or ion is like a hybrid of all of them.

The writing of resonant structures only allows the movement of

electrons. The positions of the nuclei of the atoms must remain the same in
all the structures.

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Basic criteria adapted to analyze the
stability of each resonance structure
Resonance structures exist only on paper. They do not exist as
such. Resonant structures are useful because they allow representation
molecules, ions, and radicals for which a single one is inadequate
Lewis structure. Then two or more of these structures are written and
they are called resonance structures or resonance contributors. The
structures are connected with a double-headed arrow («), and it is said that the
A molecule, radical, or real ion is like a hybrid of all of them.
The writing of resonant structures only allows the movement of
electrons. The positions of the atomic nuclei must remain
the same in all structures. Structure 3, for example, is not a
resonant structure of the allylic cation, because to form it would be necessary
move a hydrogen atom, and this is not allowed.

3. All structures must be proper Lewis structures. They should not be

They must write structures in which carbon has five bonds.
example:

Ésta no es una estructura resonante adecuada para el metano porque el

carbon has five bonds. The elements of the first row (period)
important elements of the Periodic Table can have more than eight electrons in their
Valencia cape.
4. All resonance structures must have the same number of
unpaired electrons. The following structure is not a structure
resonant for the allyl radical, because it contains three unpaired electrons and
the alilo radical has only one.

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5. All the atoms that are part of the delocalized system must be
find in the same plane or be nearly planar. For example, the 2,3-di-tert-
1,3-butadiene behaves like a non-conjugated diene because the
huge tert-butyl groups distort the structure and prevent the bonds
doubles are not in the same plane. Because they are not in the same plane, the
the orbitals of C-2 and C-3 do not overlap, which prevents the
offshoring and, therefore, resonance.

The energy of the real molecule is lower than what could be estimated for
any contributing structure. For example, the real allyl cation is more
established that what any of the resonant structures would indicate
separated. Structures 4 and 5 resemble primary carbocations, and even the
Allyl cation is more stable, has lower energy, than a secondary carbocation.
It is frequent what the chemicals call them a this type from
stabilization by resonance.

Benzene has a strong stabilization due to resonance, because it is a

hybrid of the two equivalent forms that follow:

7. The equivalent resonance structures make the same contribution.

for the hybrid, and the systems they represent have great stabilization
through resonance. Structures 4 and 5 contribute equally to the cation.
alílico because they are equivalent. They also provide a contribution
important stabilizer and explains the unusual stability of the
allylic cations.
8. Structures that are not equivalent do not make the same contribution.

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general terms, the more stable the structure by itself,
greater is your contribution to the hybrid. For example, the following cation is
a hybrid of structures 6 and 7. Structure 6 makes a contribution
greater than 7 because 6 resembles a tertiary carbocation, while
It resembles a primary cation, and tertiary cations are more stable.

The fact that it makes a greater contribution means that the partial burden
the positive charge of the hybrid carbon will be greater than the partial positive charge of
carbonod. It also means that the bond between the carbons will be stronger.
similar to a double bond that the union between the carbons.

The following rules help make decisions about stabilities

relative to resonance structures.

The more covalent bonds a structure has, the more

stable. This is exactly what is expected, because it is known that the
The formation of a covalent bond decreases the energy of the atoms.
This means that, among the following structures for 1,3-
butadiene, the most stable one, and the one that carries out the
greater contribution because it contains an additional link.

b. The structures in which all the atoms have the electrons

The complete Valencia layer is especially stable and makes

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 greater contributions for the hybrid (it is what is expected based on the
What is known about links). This means, for example, that12hace
a greater stabilizing contribution to the cation below than 11, because
all its atoms have a complete shell. It is also worth noting
What has more covalent bonds than (ver rulea).

c. The separation of charge decreases stability. The separation of

the supposed load requires energy; therefore, the structures in which
the opposite charges are separated, they have greater energy,
less stability than those without charge separation. This
it means that between the two following structures of vinyl chloride, the
structure13 makes the greatest contribution because it has no loads
separated.

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 Conclusion

The inductive effect can be exerted by a substituent, which will polarize in a manner
a permanent link. This action is transmitted through the carbon chain.

The inductive effect occurs when atoms or molecules join a carbon atom.
atomic groups that accept electrons (electrophilic agents); the most notable exception
important are the alkyl groups (-R) which are electron donors
(neutrophilic agents).

Resonance structures are interconvertible through one or more

displacements of electrons.

All canonical structures must have the same number of electrons.

disappeared. Not all canonical forms contribute equally to the hybrid.

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 Bibliography
Web portals:

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