Agua y Efecto Hidrofóbico

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 The Water Environment

• 70% of cell is water

• Hydrogen bond
• Hydrophilic and hydrophobic
• Acid and base
• Proton and hydroxyl
• Non-covalent interactions in water: Ionic
bonds, hydrogen bonds, van der waals
attractions, hydrophobic “effect” (force)

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Acid
Donate a proton

Base
Absorb a proton or donate OH-
NH3+H2O->NH4++OH-
NaOH->Na++OH-

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Ionic bonds in Water

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Introduction to Organic Molecules and Functional Groups
Physical Properties—Solubility
• Since butane and acetone are both organic compounds having a C—
C and C—H backbone, they are soluble in the organic solvent
CCl4. Butane, which is nonpolar, is insoluble in H2O. Acetone is
soluble in H2O because it contains only three C atoms and its O
atom can hydrogen bond with an H atom of H2O.

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Introduction to Organic Molecules and Functional Groups
Physical Properties—Solubility
• To dissolve an ionic compound, the strong ion-ion interactions must
be replaced by many weaker ion-dipole interactions.

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Introduction to Organic Molecules and Functional Groups
Physical Properties—Solubility
• The size of an organic molecule with a polar functional group determines
its water solubility. A low molecular weight alcohol like ethanol is water
soluble since it has a small carbon skeleton of  five C atoms), compared
to the size of its polar OH group. Cholesterol has 27 carbon atoms and
only one OH group. Its carbon skeleton is too large for the OH group to
solubilize by hydrogen bonding, so cholesterol is insoluble in water.

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Introduction to Organic Molecules and Functional Groups
Physical Properties—Solubility
• The nonpolar part of a molecule that is not attracted to H2O is said to be
hydrophobic.
• The polar part of a molecule that can hydrogen bond to H2O is said to be
hydrophilic.
• In cholesterol, for example, the hydroxy group is hydrophilic, whereas the
carbon skeleton is hydrophobic.

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Introduction to Organic Molecules and Functional Groups

Application—Vitamins
Vitamins are either lipid or water soluble.

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• Water is an effective
solvent as it can form
hydrogen bonds.
– Water clings to

polar molecules
causing them to be
soluble in water.
 Hydrophilic -

attracted to
water
– Water tends to

exclude nonpolar
molecules.
 Hydrophobic -

repelled by water 15
• Water transports molecules dissolved in it
– Blood, a water-based solution, transports

molecules of nutrients and wastes

organisms
– Nutrients dissolved in water get

transported through plants

– Unicellular organisms that live in water

absorb needed dissolved substances

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Introduction to Organic Molecules and Functional Groups
Application—Soap

Soap:
Soap molecules have
two distinct parts—a
hydrophilic portion
composed of ions
called the polar head,
and a hydrophobic
carbon chain of
nonpolar C—C and
C—H bonds, called
the nonpolar tail.

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Introduction to Organic Molecules and Functional Groups
Application—The Cell Membrane

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Introduction to Organic Molecules and Functional Groups
Application—The Cell Membrane
Transport Across a Cell Membrane:
• Polar molecules and ions are transported across cell membranes encapsulated
within molecules called ionophores.
• Ionophores are organic molecules that complex cations. They have a hydrophobic
exterior that makes them soluble in the nonpolar interior of the cell membrane, and
a central cavity with several oxygens whose lone pairs complex with a given ion.

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Introduction to Organic Molecules and Functional Groups
Application—The Cell Membrane
Transport Across a Cell Membrane:

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Introduction to Organic Molecules and Functional Groups
Application—The Cell Membrane
Several synthetic ionophores have also been prepared, including one group
called crown ethers.
Crown ethers are cyclic ethers containing several oxygen atoms that bind
specific cations depending on the size of their cavity.

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 Properties of Liquids

Surface tension is the amount of energy required to stretch or

increase the surface of a liquid by a unit area.

Strong
intermolecular
forces

High surface
tension

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11.3
 Properties of Liquids

Cohesion is the intermolecular attraction between like molecules

Adhesion is an attraction between unlike molecules

Adhesion

attracted to glass

Cohesion

attracted to each other

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11.3
 Cohesion

• Water clings to polar

molecules through
hydrogen bonding
– Cohesion refers to

attraction to other
water molecules.
 responsible for

surface tension
 a measure of the
force necessary to
stretch or break
the surface of a
liquid
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 Adhesion

– Adhesion refers
to attraction to
other
substances.
 Water is

adhesive to
any substance
with which it
can form
hydrogen
bonds.
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 water evaporates from
Capillary action leaves = transpiration

adhesion,
cohesion and
capillary action
water taken up by
roots

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•trees have specialized structures to transport water:
xylem and phloem “plumbing”
• water molecules are “dragged” from the roots to the
top of the tree by capillary action and cohesion:
hydrogen bonds help water molecules to each other 27
 Properties of Liquids

Viscosity is a measure of a fluid’s resistance to flow.

Strong
intermolecular
forces

High
viscosity

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11.3
 Water is a Unique Substance

Maximum Density
40C
Density of Water

Ice is less dense than water

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11.3
La naturaleza
dipolar de la
molécula de agua
 en modelos: (a) de esferas y
varillas, y (b) espaciales.
 hay un ordenamiento
tetraédrico de las uniones O—H
y de los pares de electrones
libres del oxígeno.
 los H tienen cargas parciales
positivas y el O carga parcial
negativa.
 (c) dos moléculas de agua
formando un puente hidrógeno.
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Estructura del hielo
 Cada molécula de agua forma el
máximo de 4 puentes hidrógeno en
una red cristalina regular.
 En el agua líquida, cada
molécula forma un promedio de
3.4 puentes hidrógeno con otras
moléculas de agua.
 La red cristalina del hielo ocupa
mas espacio que el mismo número
de moléculas de agua líquida. El
hielo es menos denso que el agua
líquida y por eso flota.
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Fatty Acids

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Phospholipid (amphipathic)

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La unión hidrofóbica (1)

Los compuestos
apolares
restringen la
movilidad de los
puentes
hidrógeno
del agua y
producen
cambios
energéticos
desfavorables en
la estructura del
agua

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La unión hidrofóbica
(2)

Los ácidos grasos de

cadena larga tienen
cadenas alquílicas
hidrofóbicas, que al ser
introducidas en el agua,
se rodean de moléculas
de agua altamente
ordenadas

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La unión hidrofóbica
(3)
 Cuando las moléculas de ácidos
grasos se agrupan lateralmente
disminuye el número de moléculas
de agua “ordenadas”
 Similarmente al agruparse en
micelas, los acidos grasos exponen
una superficie hidrofílica y
minimizan el ordenamiento de las
moléculas de agua. La micela se
estabiliza por el efecto entrópico de
aumentar el agua desordenada

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Vista superior de la generación de una unión hidrofóbica
Cada cadena hidrocarbonada (de 9 C) está rodeada por 4
columnas de 6 moléculas de agua cada una. La asociación de
dos moléculas de ácido cáprico (10 C) elimina 2 columnas de
moléculas agua de la “celda del solvente”

G = H – T S H = H2 –H1 y S = S2 – S1

Cálculo de H (para el complejo molecular descripto):

Ruptura de 12 uniones H2O/CH2= + 120 kJ
Formación de 9 uniones =H2C/H2C= - 36 kJ
Formación de 6 uniones H2O/H2O - 120 kJ
H = - 36 kJ
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 Cálculo de S:
Asimilando el cambio a agua(s) => agua (l)
con S = 22 J/K . mol de agua y 12 moles de agua
(22 J/K x 12 x 300 K) = 79.2 kJ TS = - 79 kJ
G = H – T S
G = - 36 kJ – 79 kJ
G = - 115 kJ
Proceso espontáneo

A los dominios (espacios) hidrofóbicos compartidos entre moléculas,

que excluyen a las moléculas de agua, se los denomina unión
hidrofóbica. En realidad, no hay una unión hidrofóbica, sino una serie
de atracciones tipo van der Waals y tipo London sumados a los
puentes hidrógeno del solvente (agua). Las uniones hidrofóbicas son
responsables de la formación de micelas, monocapas y bicapas
lipídicas, membranas biológicas y plegamientos de proteínas.
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 Membranas Biológicas
Constituidas por una bicapa de fosfolípidos y proteínas
integrales y periféricas (Singer y Nicholson, 1961)

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Nobel de Química 2003: hallazgos sobre diminutos canales
de la membrana celular

La Nación, jueves 9 de octubre de 2003

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