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La Química,

la catálisis y la vida

Ernesto Carmona Guzmán

Universidad de Sevilla – Consejo Superior de Investigaciones Científicas

O

O

H

H

H

H

O

O

O

O

Fe Fe

O

O

C

C

O

O

C

C

Si

Si

O

O

O

O

O

O

O

O

C

C

O

O

(2)
(3)
(4)

1H +1H =2H + e+ +Q

2H +1H =3H +J

3H +3H =4H + 21H

41H 4He + 2e+ + 2Q (26,72 MeV)

(1)

(2)

(5)
(6)
(7)

« Before the word for it (in any language)

came to be, there was chemistry.

For one defining aspect of human

beings has always been

the meld of mind and hands

in transforming matter. »

Roald Hoffmann

Premio Nobel de Química 1981.

The New Chemistry. N. Hall, Ed.

Cambridge Univ. Press, 2000

D. Hodgkin

(8)

Nature, 2002, 418, 515

(9)

A. Corma, et al. Nature 2009, 458, 1154

(10)

La Química de

la Vida

SíNTESIS

QUÍMICA

Átomos,

Moléculas

Otras Moléculas,

Compuestos, materiales,...

N2(g) + 3H2(g) [cat] 2NH3(g)

Industria

(11)

““

““

A

A

catalyst

catalyst

is

is

a

a

substance

substance

which

which

affects

affects

the

the

rate

rate

of

of

a

a

chemical

chemical

reaction

reaction

without

without

being

being

part

part

of

of

its

its

end

end

products

products

””

””

W.

W.

Ostwald

Ostwald

,

,

1900.

1900.

Premio

Premio

Nobel

Nobel

de

de

Qu

Qu

í

í

mica,

mica,

1909.

1909.

““

““

A

A

catalyst

catalyst

is

is

a

a

substance

substance

which

which

increases

increases

the

the

rate

rate

at

at

which

which

a

a

chemical

chemical

reaction

reaction

approaches

approaches

equilibrium

equilibrium

without

without

becoming

becoming

itself

itself

permanently

permanently

involved

involved

””

””

P.

W.

N.

M.

van

P.

W.

N.

M.

van

Leewen

Leewen

,

,

Homogeneous

Homogeneous

Catalysis

Catalysis

Kluwer

(12)

W.

W.

Crooks

Crooks

,

,

1898

1898

(68th

(68th

meeting

meeting

of

of

the

the

British

British

Association

Association

for

for

the

the

Advancement

Advancement

of

of

Science

Science

):

):

““

““

……

……

all

all

civilized

civilized

nations

nations

stand

stand

in

in

deadly

deadly

peril

peril

of

of

not

not

having

having

enough

enough

to

to

eat

eat

……

……

the

the

fixation

fixation

of

of

atmospheric

atmospheric

nitrogen

nitrogen

is

is

one

one

of

of

the

the

great

great

discoveries

discoveries

awaiting

awaiting

the

the

ingenuity

(13)

““

““

forhisstudiesofchemicalprocessesonsolid

for

his

studies

of

chemical

processes

on

solid

surfaces"

surfaces"

.

.

"in

recognition

of

their

contributions

to

the

invention

"inrecognitionoftheircontributionstotheinvention

and

development

of

chemical

high

pressure

methods"

anddevelopmentofchemicalhighpressuremethods"

"for

the

synthesis

of

ammonia

from

its

"forthesynthesisofammoniafromits

elements"

elements"

G.

G. ErtlErtl, Premio Nobel de Qu, Premio Nobel de Quíímica 2007mica 2007

C. Bosch, Premio Nobel de Qu

C. Bosch, Premio Nobel de Quíímica 1931 (F. mica 1931 (F. BergiusBergius))

F. Haber, Premio Nobel de Qu

(14)

Catalizadores

de

tres

v

Catalizadoresdetresv

í

í

as

as

(15)
(16)

A. Werner.

Premio Nobel de Química, 1913

M

L

L

L

L

L

L

M L

6

(O h)

M

L

L

L

L

M L

4

(T d)

CoCl

3

(N H

3

)

6

(am arillo)

CoCl

3

(N H

3

)

5

(púrpura)

CoCl

3

(N H

3

)

4

(verde y violeta)

CoCl

3

(N H

3

)

3

(dos isóm eros)

Cr

Fe

CH

3

W

CH

3

H

3

C

CH

3

CH

3

H

3

C

CO

Cr

CO

I

C

OC

CO

CH

3

Ta CH2 CH3

(17)

NH

3

Ru

NH

3

H

3

N

N

H

3

N

NH

3

N

2+ PCy3 W PCy3 OC OC CO H H

Cl

Ti

Cl

P

P

Cl

CH

2

H CH

2

Xe

Au

Xe

Xe

Xe

2+

H

SiH

3

Mo

R

2

P

R

2

P

CO

PR

2

PR

2

O

Co

NH3

H3N NH3 H3N

CH3

5+ NH3

Co

O

H3N NH3 H3N

CH3

Algunos procesos catalíticos homogéneos

Catálisis Ziegler – Natta para la producción de poliolefinas (metalocenos como catalizadores).

Hidroformilación de alquenos catalizada mediante complejos de cobalto (CoH(CO)4), o de rodio (RhH(CO)(PPh3)3). Síntesis de diversos productos oxigenados (alcoholes detergentes….).

Síntesis del ácido acético: Monsanto (Rh) y Cativa (Ir)

(18)

La Quiralidad es un fenómeno común en la naturaleza: Proteínas, Carbohidratos, Acidos Nucleicos

Las moléculas, como los objetos macroscópicos, tienen una estructura tridimensional. La quiralidad de una molécula es una consecuencia de su estructura espacial.

Productos Quirales: Efecto Biológico

H

X

Z

Y

Y' X'

H

X Y

Z

Y' X'

Z' Z'

A B

Enantiómeros y Propiedades Biológicas

>

Naproxeno

CO2H

MeO

Tóxico

CO2H

MeO

(19)

(R)-limonene (S)-limonene

mirror plane

Rh PPh3

Ph3P Cl

PPh3 M P S S P + O O PPh2 PPh2 P Ph OMe P Ph MeO (Rh, Ir) (Osborn, Schrock) DIOP (Kagan)

Di PAMP (Knowles)

PPh2

PPh2

BINAP (Noyori)

(20)

P Ph OMe P Ph MeO Di PAMP (Knowles)

HO OH H C C N(H)C(O)R C(O)OR

1. H2, [Rh(DiPAMP)(S)2] +

2. H3O +

HO

OH CH2

C

H3N H

CO2

-L-dihidroxifenilalanina (L-DOPA)

W. Knowles, Monsanto (1974)

+

(21)

W. Knowles, R. Noyori, B. Sharpless, Premio Nobel de Química, 2001.

Importancia de los

Productos Quirales

en la Industria Farmacéutica

N OH HO COO -F NH O Ca2+ 2 H O O HO O O N H N SO N

O CF3 N

H N SO N

O O

Total ventas productos 1-5:

17.600 millones

(22)

P Ph OMe P Ph MeO Di PAMP (Knowles)

HO OH H C C N(H)C(O)R C(O)OR

1. H2, [Rh(DiPAMP)(S)2] +

2. H3O +

HO

OH CH2

C

H3N H

CO2

-L-dihidroxifenilalanina (L-DOPA)

W. Knowles, Monsanto (1974)

+ NH2 HO HO

Dopamina

NH2 COOH HO HO

L-Dopa

H2N

HOOC OH

OH

D-Dopa

(23)

OH O

OH

HO NH2

[dopamina descarboxilasa]

NH2

OH HO

+ CO2

L-dopa dopamina

OH O

HO H N CH3

HO

NH2

(24)

Richard F.

Richard F. HeckHeck

Ei

Ei--ichiichiNegishiNegishi

Akira Suzuki

Akira Suzuki

PREMIO NOBEL DE QU

Figure

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Referencias

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