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Mesomeric E!ect
Oct 19, 2015 • Download as PPT, PDF
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Mesomeric (or resonance) e!ect refers to the

polarity produced in a molecule throughRead
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Practical
Solutions for

Mesomeric E!ect
1. 1
2. MesomericMesomeric E!ect/Resonance
E!ectE!ect/Resonance E!ect Amina Tariq Pharm-D 15987 RIPS 2
3. INTRODUCTION OFINTRODUCTION OF
MESOMERISMMESOMERISM THE CONCEPT OF MESOMERISM
MESOMER AND MESOMERIC EFFECT WERE INTRODUCE BY INGOLD
IN 1938. IT IS ALSO KNOWN AS OLD FASHIONED TERM FOR
RASONANCE 3
4. 4
5. EXAMPLEEXAMPLE
6. Mesomeric E!ect ( M-E!ect)Mesomeric E!ect ( M-E!ect) It
refers to the polarity produced in a molecule as a result of
interaction between two pi bonds or a pi bond and lone pair of
electrons. The electron withdrawing or releasing e!ect attributed
to a substituent through delocalization of π electrons, which can be
visualized by drawing various canonical forms, is known as
mesomeric e!ect or resonance e!ect. It is symbolized by M or R. 6
7. TYPESTYPES Negative mesomeric e!ect (-M or -R): It is
shown by substituents or groups that withdraw electrons by
delocalization mechanism from rest of the molecule and are
denoted by -M or -R. The electron density on rest of the molecular
entity is decreased due to this e!ect. E.g. -NO2, Carbonyl group
(C=O), -C N,≡ -COOH, -SO3H etc. 7
8. Negative mesomeric e!ect (-M or -R):Negative mesomeric e!ect
(-M or -R): Example: 1) The negative resonance e!ect (-R or -M) of
carbonyl group is shown below. It withdraws electrons by
delocalization of π electrons and reduces the electron density
particularly on 3rd carbon. 8
9. Negative mesomeric e!ectNegative mesomeric e!ect (-M or -R):
(-M or -R): 2) The negative mesomeric e!ect (-R or -M) shown by
cyanide group in acrylonitrile is illustrated below. The electron
density on third carbon decreases due to delocalization of π
electrons towards cyanide group. 9
10. 10
11. Positive resonance orPositive resonance or mesomeric e!ect
(+M or +R):mesomeric e!ect (+M or +R): The groups show
positive mesomeric e!ect when they release electrons to the rest of
the molecule by delocalization. These groups are denoted by +M or
+R. Due to this e!ect, the electron density on rest of the molecular
entity is increased. E.g. -OH, -OR, -SH, -SR, -NH2, -NR2 etc 11
12. Positive resonance orPositive resonance or mesomeric e!ect
(+M or +R):mesomeric e!ect (+M or +R): The -NH2 group in aniline
also exhibits +R e!ect. It releases electrons towards benzene ring
through delocalization. 12
13. Positive mesomeric e!ect (+M or +R):Positive mesomeric e!ect
(+M or +R): 1).In phenol, the -OH group shows +M e!ect due to
delocalization of lone pair on oxygen atom towards the ring. Thus
the electron density on benzene ring is increased particularly on
ortho and para positions. 13
14. 14
15. 15
16. 16
17. SIGNIFICANCESIGNIFICANCE It describe the charge
distribution in a molecule ,thus provide an e!ective way of
determing the point of attack of electrophiles and nucleophiles.
Useful in explaining physical characteristics i.e bond
length,dipole moment. 17
18. 18

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