S tructural & A cid-Base

Roldan M. de Guia
Department of Biochemistry Faculty of Pharmacy University of Santo Tomas

Structural Effects
ele ct ron d eloca li zati on
CH2 .. CH Cl : ..
.. O C .. .. NH2 .. NH2

.. Cl : ..

:O: CH3 C .. O H ..

electron delocalization (Resonance)

Structural Effects

electron delocalization (Resonance)

Structural Effects

electron delocalization (Resonance)

Structural Effects
:O: C H

:O:

H

.. :O

.. :O: N+

.. NH2

Hyp ercon jugat io n

Structural Effects
H H C CH CH2 H

H

+

H C CH CH2 H

..-

..+ H C CH CH2 H

H

..H C CH CH2 H
+

H

Hyperconjugation

Structural Effects

Dienes

CH2

CH CH CH2
conjugated

cumulative

isolated

Hyperconjugation
H H C H

Structural Effects
H H C H
+

H H C H
+

..

..
-

Hyperconjugation
H H C C H

Structural Effects
O H
H O H C C H H +

O

O

Structural Effects
+

CH3

CH3

+

CH2

+

CH2 H3C

CH3 C
+

CH3

H
-

:CH3

O2N

C: H H

-

. CH

3

C. H

Induct ive Eff ect

Structural Effects

Ele ct ron at tr ac ti ng in duc ti ve
with excess positive charges R N R R those with electronegative atoms NH2 OH OCH3 F
+ +

NH3

+

NO2

Cl Br groups exhibiting orbital electronegativity C N N N

those with easily polarizable valence electrons I
-

Induct ive Eff ect

Structural Effects
δ+ δ−

Ele ct ron at tr ac ti ng in duc ti ve
H3C Cl
δ+ CH3 δ++ CH2 δ− Cl
CH3 H3C N CH3
-+

CH3

δ+ CH2

δ− O H δ+

Induct ive Eff ect
alkyl groups CH3 negative groups COO
-

Structural Effects

Ele ct ron re pe lling i nd uct ive effec t

S

-

O

-

O H3C C O
--

H3C

S

-

H3C CH C N H3C

St eric Ef fe ct

Structural Effects

Hyd ro gen B ond ing +
F H δ O N H δ+ H δ+

Structural Effects
F O N H H H δ+ δ+ δ+

H O H R O H O H H H O R

O

H
OH OH

O H O R C O H O C R

F

H C O O H

Brønsted–Lowry Acids and Bases
• An acid is a proton donor • A base is a proton acceptor

Acids and Bases

acid

base

base

acid

Note that water can act as an acid or a base

Brønsted–Lowry Acids and Bases

Acids and Bases

acid

base

conjugate base

conjugate acid

Every acid–base reaction involving proton transfer has two conjugate acid–base pairs.

Lewis Acids and Bases
• A Lewis acid is an electron pair (think empty orbital) acceptor.

Acids and Bases

A Lewis base is an electron pair (think filled donor. orbital)
The result of a Lewis acid–base reaction is often called an adduct.

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