Inductive effect

The inductive effect or I effect in organic chemistry, a charge- changing effect both I effect ( " electron-donating " ) as well as I effect ( " electron withdrawing " ) occurs. It is by electrostatic induction by means of functional groups along one or more chemical bonds triggered. the concept was developed by chemists Gilbert Newton Lewis and Christopher Kelk Ingold.

Basis

The cause of this effect is an asymmetry in the distribution of electrons in an electron- pair bond between two identical, but differently substituted atoms, or between two different atoms. Two atoms that are bound by an electron pair bond, there are two electrons share. This electron is assigned a fixed location, but they are free to move within this binding. The electrons are drawn in the event of asymmetry in the distribution of electrons on the atom, the electronegativity is higher.

There are two types of I- effects: the I effect (read: positive inductive effect) and the - I effect (read: negative inductive effect). An electronegative atom exerts a - I effect, so that the electron density is reduced at the other atom. With a I effect, the electrons are pushed away from the a atom, and thereby increasing the electron density at the other atom. The bond now has a dipole character, which is characterized by δ on the atom with the lower charge density and δ - on the atom with the high charge density. To compare the strength of the inductive effect of atoms or groups of atoms, the electronegativity of the substituent of the electronegativity of the hydrogen is compared. The greater the difference in the electronegativity, the stronger is the inductive effect.

General

Atomic bonds, depending on the electronegativity of the binding partners, be polarized, that is present as polar atomic bonds. If one of the elements more electronegative than its binding partner, so to keep the electrons more frequently in its vicinity. As a result, shifts the charge distribution, so that the electronegative element is polarized in a more or less negative. Along the bond there is a Bindungsdipolmoment.

As an example here is to lead (H2O) water. Due to the higher electronegativity, the electrons keep frequently on the oxygen atom. This is expressed by δ - close to the O atom, and by each one δ next to each of the two H atoms in the water molecule. Often, the δ - when written slightly larger oxygen. This is common because the δ - charge of the oxygen atom is double as high as that of each hydrogen atom. By vector addition of the individual Bindungsdipolmomente gives the electric dipole moment of the molecule. Bindungsdipolmomente and electric dipole moment should not be confused with each other: Thus, symmetrically built molecules, such as carbon dioxide ( O = C = O) polar bonds but no electric dipole moment.

The inductive effect can disregard affect other atoms or groups of atoms over several bonds. However, the strength decreases with the square of the distance. It is estimated that affect inductive effects no more than three adjacent bonds. If an inductive effect in a molecule such as 1 - fluoropropane, so the inductive force acts on a chain in the following atoms:

The fluorine atom triggers an induction effect, which affects the following three carbon atoms. Most is the induction effect on the first carbon atom directly bonded to the fluorine atom, this is indicated by symbol δ . However, the strength decreases, the more the affected carbon atom is removed from the fluorine atom. The second carbon atom in the alkyl chain of the induction effect is lower, which is expressed by the mark δδ . In turn, is much lower, the inductive effect of the fluorine atom affects the further away from the fluorine atom third carbon atom, which is expressed by the mark δδδ .

In general, I considered effects in more complex compounds. This makes it possible to analyze the behavior of the compounds. For example, the - I effect has wider implications in trichloroacetic acid. In practice this connection three chlorine atoms on the carbon atom a -I effect. This makes the C atom attracts the electrons of the carbon atom adjacent to it to be, which makes this C atom attracts electrons from neighboring and singly bound oxygen to him. The bond between the O atom and its related H atom is weakened and the H ion ( proton) very easily be split off.

I effect

A I effect have particles that act electron-donating. This happens for example when the particle is negatively charged and has a low electronegativity. Similarly, the I effect can be observed in the formation of hybrid orbitals, acts such as the methyl group CH3, even though this is due to the C- C single bond no reason electron-donating.

The I effect also has an influence on the position of the second substituents in electrophilic aromatic substitution. A first deputy with I effect pushes electrons into the system. However, the inductive effect increases in the distance quickly. If substituents are attached in the ortho- or para-position, it is formed as a transitional state is a cation which can be represented in a number of resonance forms. In this case, there is always a resonance formula where the positive charge of the cation is in the C- atom has the Erstsubstituenten bound. Characterized in that the electrons are shifted in directly next to the positive charge at this resonance formula, the cation is stabilized. The more stable the transition states for the ortho or para position have a relatively low energy and are therefore also reached relatively quickly (see Hammond postulate ). It is also said that Erstsubstituenten conduct with I effect in the ortho or para position. The para position is preferred because of less steric hindrance prior to the ortho position.

- I effect

The - I effect have atoms, the electron-withdrawing effect. This comes about usually by high electronegativity or a positive charge. Strongly electronegative particles attract particularly strong on electrons.

Effects of the induction effect

The effects of the induction effect are that other polar molecules now they focus on the said molecule and can attack it. In addition, the induction effect has an influence on the position of the second substituent on the benzene. Radicals or carbenium ions ( carbocations ), ie particles with electron deficiency are stabilized by substituents with I effect and destabilized by those with - I effect. Apart from the inductive effect has a significant influence on the acid strength of a molecule. If a molecule, for example, over a strongly electronegative ( electron-withdrawing ) substituents, the elimination of a proton easier (-I effect), the acid strength is correspondingly large. Conversely, an electron-donating substituent in a low acid strength ( I effect ).

Inductive acting groups

Here are some inductively acting groups are listed:

I (positive inductive effect)

• T-butyl -C (CH3) 3
• I-propyl -CH (CH3) 2
• Alkyl -R

I = 0 (no inductive effect)

• Hydrogen atom H

-I ( negative inductive effect)

• Oxygen in the carbonyl -C = O
• Hydroxyl group -OH
• Iodine -I
• Bromine -Br
• Chlorine atom Cl
• Nitro group - NO2
• Amino group - NH2
• Carboxy group -COOH
• Fluorine atom -F
• Cyano group -CN