An NMR Machine reports on molecules to chemists.

4.42 4.40 4.38

4.42 4.40 4.38

spectrum

Specifically, its the nucleus of 1H that responds to the magnetic field of the NMR machine.
radio wave

Spectra Appear complicated at first glance, however, when separated into their three orthogonal dimensions...
2.27 2.26 2.25 2.24 2.23 2.22 1.97 1.96 1.95 1.90 1.90 1.88 1.88 1.87 1.85 1.64 1.61 1.61 1.61 1.58

2.27 2.26 2.25 2.24 2.23 2.22

1.97 1.96 1.95 1.90 1.90 1.88 1.88 1.87 1.85

1.64 1.61 1.61 1.61 1.58

Interpreting 1H NMR
O O

3
4.8 2.0 4.6 4.4

?
4.2 4.0

2.0 3.8 3.6 3.4 3.2 3.0 2.8 2.6 2.4 0.9 2.2 2.0

2.1 2.1 1.8 1.6 1.4 4.8 4.6 2.0 4.4 4.2 4.0 3.8 3.6 3.4 3.2

2
2.0 3.0 2.8 2.6 2.4 0.9 2.2 2.0 2.1 2.1 1.8 1.6 1.4

m Che ft Shi
4.42 4.40 4.38

ical

Chemical shift reports on the energy needed to flip a spin (relative to TMS).

The Location along the horizon tells us mostly about its electron density.
E More upfield ed shield

2.27 2.26 2.25 2.24 2.23 2.22

TMS

1.97 1.96 1.95 1.90 1.90 1.88 1.88 1.87 1.85

only some parts of the molecule are reported. 1H, everywhere in organic molecules, is happily also one that Reports AND gives simple reports.

F2C CF2 F3C

1.64 1.61 1.61 1.61 1.58

Jon Chui / jkwchui@uvic.ca

...Can often tell us Everything we need to solve a mystery molecule.

N.B.: Details accompanying this overview in upcoming spreads. Stay tuned!

to Which inductive and resonance effects both contribute additively

higher edensity upfield, shielded, moves right

less e downfield Deshielded

the remainder is mostly from circulating current - like those from aromatic rings and alkynes.
2. Induces 2. Induces

2.27 2.26 2.25 2.24 2.23 2.22

1.97 1.96 1.95 1.90 1.90 1.88 1.88 1.87 1.85

1.64 1.61 1.61 1.61 1.58

Elect ro enviro nic nment

Center of 0 ppm cluster

4.42 4.40 4.38

3. Ar-H deshielded

3. yne-H shielded

2.0 2.0 4.8 4.6 4.4 4.2 4.0 3.8 3.6 3.4 3.2 3.0 2.8 2.6 2.4 2.2 0.9 2.0

2.1 2.1 1.8 1.6 1.4

small; measured in parts per million (PPM)

1. moving electrons

1. moving electrons

Common Functional Groups can be identified by comparing to reference charts.

2.1 1.8

H H H H H H H

The peak area is proportional to the number of protons.

pe

Exceptions! 2.0

2.1 1.6

in

g
2.0 4.6 4.4 4.2 4.0 4.8

a ar k ea
3.8

1 :3
3.0 2.8

1 :3

2.6

2.4

3.6

3.4

3.2

exchangeable protons in 2.0 protic 2.2 solvents show up less than the formula would predict.
e.g.

0.9

1.4

one set of peaks

This is integrated by the spectrometer and is thus also called the integration.

height

:
Coupling (and Multiplicity) tells us about the relationships between a proton and its (spin-active) neighbours. Lets look at its origins.

= 1 :3

pr

to

ns

O O F2C CF2 F3C

Ne

ig

ur

one set of protons If As neighbours are spin-silent (like 12C), then they do not affect the energy required to flip As spin. B But if As neighbour B is spin-active, i.e., B has a little magnetic field of its own, then A will experience the normal field plus or minus Bs contribution. In the spectrum, A would be split into two lines, centering around where the original line would be. The number of lines (N) A displays tells us the number of neighbour Bs it has. For proton neighbours its always

N = #B + 1

(Can you explain why?)

Proton A

Each proton requires a particular energy to flip its spin.

And thus in a population of A, half the spin would take more energy to flip, and the other half less.

The size of the gap, i.e., the coupling constant J, tells us how strongly A and B interact with one another, and thereby their relationship. Relationship between protons can tell us a great deal, and we will dedicate a full spread to its study.