Espectroscopía

AFM images (FOTOs de moléculas!!!!)

Real-Space Imaging of a Single-Molecule Monoradical Reaction
Shaotang Song et al., J. Am. Chem. Soc. 2020
https://doi.org/10.1021/jacs.0c05337
ESPECTRO ELECTROMAGNÉTICO
excites vibrational energy levels
 APARIENCIA DEL ESPECTRO IR

wavenumber = v Zona de huellas digitales y de grupos funcionales

An absorption band due to a particular functional group

always appears in the same general region.
 Generalizations
1 k
 =
2c M
k = force constant of bond (proportional to bond strength)

M = reduced mass of atoms (proportional to mass of atoms)

1. stronger bonds absorb at higher wavenumber (larger k)

2. stretches absorb at higher wavenumber than bends (larger k)
3. bonds to H absorb at higher wavenumber (smaller mass)
4. polar bonds have more intense absorptions (smaller %T)
 Enlaces sencillos a Hidrógeno
decreasing bond strength

O
O-H > N-H > CspH > Csp2H > Csp3H > CH
3000 2830
3550-3200 cm-1 3400-3200 3300 3100
-2850 -2700
intense (polar) less intense -3000
less broad two
very broad
NH2 has 2 bands
(H bonding)
H NH has 1
O H O
3000 cm-1 divides
sp2 and sp3
Double Bond Region
O N C
C C C

~1700 cm-1 lower 1660-1640

very intense (polar) wavenumber less intense
very useful (uncommon) (nonpolar)

four bands near 1600, 1580, 1500, and 1450

variable position and intensity (use caution)
Triples enlaces
C N C C

2260-2200 2150-2100
more intense less intense
less polar
For symmetrical alkynes,
this band can be very weak.

CH3CH2 C C CH2CH3
Csp3-H (<3000)
3000 divides Csp2-H and Csp3-H
Csp-H
 Csp3-H
Csp2-H
2. 13C Magnetic Resonance Spectroscopy

Apariencia
La densidad
electrónica protege
C-O vs C-N
Cuántas señales debe dar?
Simule el espectro
 CH3 CH3 CH3
CH3

A cuál xileno
CH3
corresponde? CH3
 Integral
area under a peak is
proportional to the
number of H’s

multiplicity
number of peaks in group
info about nearby H’s

RMN 1H Chemical shift

position on x-axis
info about C to which the H is bonded
Inductive Effects
Electronegative X pulls electrons away from H;
X C H H is deshielded; appears more downfield

C is slightly more electronegative than H

Simule el espectro del siguiente compuestos
 Qué compuesto es?
Cómo se calcula el IDH?

DU = 1
 Cómo vamos a usar esta información
• El tolueno se oxida a alcohol bencílico

Que no sea gato no significa que sea perro.

¿Puede juzgar por ausencia?

Qué señales caracterizan al producto que no tiene el reactivo.

Imagine que lo hace en el laboratorio, qué señales buscaría?

A veces funciona mejor el IR a veces RMN

Ud. debe saber qué escoger