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![Page 1: To contents page A-level and Undergraduate Bridging between Proton NMR Created by Chris Phillips whilst a final year MChem student in the Department of.](https://reader035.fdocuments.in/reader035/viewer/2022062304/56649d095503460f949db5ba/html5/thumbnails/1.jpg)
To contents page
A-level and Undergraduate
Bridging between
Proton NMRCreated by Chris Phillips whilst a final year MChem student in the Department of Chemistry at the
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Click on the topic you wish for information on:
Magnetic resonance
Spectra Splitting patterns
Interpreting spectra quiz
ShieldingEquipment
Change page
Return to contents
Text More information on that term
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Magneticresonance
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• One of the main features of NMR is the use of magnetic fields• Moving charges produce their own magnetic fields. This
means nuclei have a field. • Nuclei align in a magnetic field, in a similar way to bar
magnets aligning when next to other magnets.• You would have to apply force to move the magnet against the
fields of the other magnets, making the alignment shown below, the most stable alignment
• Without the other field, the magnet can lie in any direction
N
S
Externalmagnetic field
S
N
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• A nucleus’ alignment in a field is described through the quantum property named ‘spin’.
• The quantum property of spin can be represented by saying a nucleus can align in 2 directions (‘up’ and ‘down’), as a bar magnet can in another magnetic field.
• For protons, these 2 directions or spin states are described by quantum numbers +1/2 and -1/2.
• Without a field, the spin state does not matter, they are equally energetically favourable, like a bar magnet without other magnets nearby.
+1/2 -1/2
‘up’ ‘down’
N
S
Direction of field
Externalmagnetic field
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When a magnetic field is applied (B0), one spin state becomes higher
in energy, and one lower
States are separated in energy by an amount, ΔE
The fields of the nuclei align with or against the applied magnetic field
The stronger the field, the greater the energy gap between ‘up’ and ‘down’ states
Larger separation means more nuclei are in the lower energy state
‘Magnetic resonance’ is using radiowaves to swap nuclei between different spin states; changing the alignment of nuclei within the field
+1/2
-1/2
B0
ΔE
‘Against’ is higher in energy
‘With’ is lower in energy
N
S
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In NMR, radiofrequency pulses can change alignments to an excited energy state, the higher energy state
The frequency required is unique to the particular energy gap, depending on a proton’s environment
After a pulse, protons release energy as they settle back to their natural state; this is relaxation
Radiofrequency emissions during relaxation are recorded against time
A mathematical process, called a Fourier Transformation, converts the signal into the NMR spectrum
How does NMR use spin?
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https://www.youtube.com/watch?v=1CGzk-nV06g
The principles of magnetic resonance, from the perspective of MRI:
https://www.youtube.com/v/1CGzk-nV06g
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1. Apply magnetic field
2. Begin pulses3. Stop pulses
Outside of a field – random orientations
Field applied – separates spin up and down states
Try your own magnetic resonance experiment!
Fourier transformation
Detector
Radiofrequency pulse excites nuclei so they can spin flip
Excited spin state relaxes to original alignment. Radiofrequency emitted.
4. Restart
B0
B0
Population of energy levels
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1. Apply magnetic field
2. Begin pulses3. Stop pulses
Outside of a field – random orientations
Field applied – separates spin up and down states
Try your own magnetic resonance experiment!
Fourier transformation
Detector
Radiofrequency pulse excites nuclei so they can spin flip
Excited spin state relaxes to original alignment. Radiofrequency emitted.
B0
B0
Population of energy levels
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Equipment
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The main principle of NMR, is the use of
A field is applied to a proton, which causes
alignment with, or against, the magnetic field A radiofrequency pulse, specific to the nucleus
involved, ‘flips’ the alignment Radiofrequency emissions are recorded, and are
unique to the nucleus being observed.
Magnetic resonance is the excitation of nuclei using radiofrequencies while a magnetic field is applied
x
magnetic resonance
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How to run an NMR experiment:
https://www.youtube.com/v/kPx6BlJj5DU
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Click on a label for more information:
Radiowavegenerator Detector
Magnetic field (B0)
Magnet
Produces pulses of radiowaves which change the alignment of protons
Generates applied magnetic field which creates an energy difference in spin states and causes alignment More
The detector picks up energy emitted as protons relax
Signal is then converted into NMR spectrum for analysis, using Fourier Transformation
A Basic NMR schematic
The magnets are superconductors, cooled to 4K (as close as possible), and submerged in liquid helium
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Fourier Transformation• The Fourier Transformation is a mathematical function
• It converts the signal produced by relaxing nuclei into the NMR spectrum which is analysed
• The time based signal is converted into a frequency based signal
• More environments result in a more complicated signal as characteristic frequencies superimpose
Chemical shift/ ppm
Time / s
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Spectra
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Each peak (or ) represents a unique proton environment
An environment is a group of equivalent protons in a molecule.
Equivalent protons are identical All equivalent protons give the same signal
Multiplets are groups of peaks on a spectrum which collectively represent a single proton environment
Here, there are 2 proton environments: a CH3 group, and a CH2
group
multipletx
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The spectra have 'chemical shift' along the x-axis Chemical shift is related to a proton’s resonant
frequency and gives information about a proton's environment, such as the electronegativity of neighbouring atoms
Intensity, on the y-axis, is rarely marked on NMR spectra, but gives information on the number of protons within an environment
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In order to produce a value for chemical shift, tetramethylsilane (TMS) is used
TMS is a standard, assigned a chemical shift of 0 All other signals are therefore compared to TMS
Why is TMS used?
This works by comparing the frequency required for resonance in the observed environment with the resonant frequency of TMS
Chemical shift is therefore a frequency value, relative to the standard
TMS has the following key properties:
- 12 hydrogens, all identical, provides a very clear, strong signal to compare against
- Protons in TMS’s C-H bonds have the greatest electron cloud of almost all other C-H bonds, ensuring all other signals are to the left of the TMS signal
x
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NMR spectra have a 'downfield' and an 'upfield'.
As a peak's chemical shift increases in value, it moves downfield, having been
Downfield Upfield
Did you know?
Deshielding is the reduction of a proton’s electron cloud. One example of this is a neighbouring electronegative atom withdrawing electron density.As a signal is found further downfield, it means the electron cloud around the proton is less than the cloud around protons in TMS.
x
deshieldedSome protons are so well shielded, that they are more heavily shielded than TMS.This gives them a negative shift.
The protons labelled here are shielded by the delocalised electrons opposing the magnetic field.
x
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Proton NMR gives the number of hydrogen atoms present
The size of the peaks gives the relative number of protons in each environment
When a peak has been split, the area under a group of peaks is taken. This is an integrated value
Therefore, the peak will give the correct number of protons within the environment, even if the intensity has been reduced by being split into a multiplet
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• The values don't always have to be integers, the relative sizes are what's important!
• These values can sometimes be found in several locations, but are always near the peak they are assigned to
• This may be:
• Beside a line indicating which peaks have been included
• Below the peak
• On a ‘normalised’ y-axis
2.3
4.6
2.3
1
2
1
Click here for some alternate peak values.Notice they follow the same 1:2:1 ratio between the peaks
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Shielding
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Shielding determines how far , or , a peak is shifted
As a proton becomes deshielded, it is shifted further downfield, as the magnetic field is
able to affect it more
Shielding determines how nuclei interact with the magnetic field and the of the signal
The electron cloud surrounding a nucleus opposes the applied field
The more electrons, the greater the shielding around a proton, so the field is more strongly opposed
Downfield is an increasing chemical shift, as a proton is more deshielded
downfieldupfield
Upfield is the decreasing chemical shift, as a proton is more shielded
x
x
chemical shift
The resonant frequency of a proton, compared to the standard in NMR of tetramethylsilane (TMS)See section: Spectra
x
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Electronegative atoms (eg. oxygen or chlorine) will draw electron density away from the protons, deshielding them.
Less electronegative atoms like carbon will not pull electron density, leaving the proton shielded, so it is not shifted.
How does an electronegative atom
affect the cloud?Click to see
How much is a weakly withdrawing atom going
to affect the cloud?Click to see
• The electron cloud is pulled away from the proton
• The electron cloud is left mostly unchanged
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• As the proton’s electron cloud reduces, the nucleus is exposed to more of the external magnetic field (B0)
• The energy gap increases causing magnetic resonance frequency to change. This changes the emissions frequency from relaxation
• This results in a greater chemical shift and the signal appears further downfield
Downfield Upfield
Click to see how far each proton will be shifted
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• Signals tend to fall within particular ranges, depending on the environment the proton is in
• This helps identify the signal based on the chemical shift
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Splittingpatterns
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In the spectrum below, there is a signal for each environment, however, they appear split.
These split peaks are multiplets.The number of peaks in a multiplet provides information about neighbouring protons.
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Splitting is caused by the interaction between inequivalent protons, called coupling
Proton-proton coupling usually takes place 3 bonds away from each other
The number of peaks, or multiplicity, comes from the number of protons interacting
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The number of peaks follows an n+1 pattern, where n is the number of protons in the interacting environment
The number of peaks observed is the multiplicity The intensity of the peaks in a multiplet follows the
pattern of Pascal’s triangle eg. If a group of protons has 2 neighbouring
equivalent protons, it will be split into a triplet.
Singlet
Triplet
Doublet
Quartet
0 neighbouring protons
1 neighbouring proton
2 neighbouring protons
3 neighbouring protons
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The CH3 is coupled
with the CH2. There
are 2 protons, so CH
3 is split into a
triplet
The CH2 is coupled
with the CH3. There
are 3 protons and therefore split CH
2
into a quadruplet
Intensity = 1:3:3:1Intensity = 1:2:1
Click on the group to see how it will appear on the spectrum:
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Origin of the Pascal’s triangle pattern Starting simple: doublets
C CH H
Observing the signal of H, it will be split by H H interacts with H's magnetic field, H
0
The magnetic field interactions cause splitting between higher and lower energy levels
H0
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There are two possible interactions that H's field can have with H's field (H
0)
One possibility will be with, and one against the interacting field
As these states are interacting with another field, the states have different energies
C CH H
There is a 1:1 ratio distributed between these levels
This gives the doublet
1:1H0
Down(Against)
Up(With)
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As a more complicated example: quartet
This time, H interacts with H3 – three equivalent protons
Each of the spins of the three protons can be aligned with or against H0
Due to the interaction being between different magnetic fields, the different possible alignments have different energies, some of them are equivalent
C CH H3
H0
1
3 of equal energy
3 of equal energy
1
4 (n+1) peaks1:3:3:1 intensity pattern
Quartet splitting pattern
All with All against2 with, 1 against
1 with, 2 against
• Complete alignment ‘with’ is the most favourable, so is lowest in energy• The next most favourable is 2 with. But there are 3 possible combinations
which give 2 ‘with’ alignments and 1 ‘against’. These are equal in energy.
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Interpreting spectra quiz
(You may want pen and paper for this!)
With each structure, identify the correct NMRClick on the circle to confirm your answer
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?
?
?
2
6
6
2
1 1
3 3
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Good try, but have another go and see if you can work out the correct spectrum
Return to question
Try this:Identify the equivalent protons and their environments
Look to see which environment is coupling with others, how many hydrogens is it coupling to (remember: n+1)?
Check to see that the integrated intensity matches the group on the molecule
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Well done!
Click for the next question
You should have noticed that:There are two groups of equivalent protons; the single protons, and the methyl groups
The single proton split the methyl signal into a doublet
The methyl group split the single proton signal into a quartet
The single proton signal is closer to the double bond, making the signal more downfield
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Note: In solvent, due to proton exchange, the OH group does not couple
?
?
?
2
1
3
21
3
21
3
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Good try, but have another go and see if you can work out the correct spectrum
Try this:Work out how many different environments there are
Look to see which environment is coupling with others, how many hydrogens is it coupling to (remember: n+1)?
Check to see that the integrated intensity matches the group on the molecule
Return to question
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Well done!
Click for the next question
You should have noticed that:There are three environments; the methyl group, the OH group, and the pair of protons on the centre carbon
The methyl group will be split into a triplet by the pair or centre protons
The pair of protons will give a signal which is split into a quartet by coupling with the methyl group
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Note: TMS reference signal occurs at a shift of 0 Hz when present
?
?
?
4 6 6
66
4
46 6
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Good try, but have another go and see if you can work out the correct spectrum
Try this:With the integrated peaks, remember the ratio of number of protons is provided, not an absolute number of protons. Try changing the numbers while maintaining the ratio.
Consider likely chemical shifts for the signals and see how it compares with what is present
Return to question
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Well done!
Click for the end the quiz
You should have noticed that:There are three environments, excluding the TMS’s signal at 0 ppm.
The ratio of peak intensities can be easily simplified to 3:2:3, fitting the number of protons in the molecule.
The pair of protons will be more downfield due to being closer to the ester functional group, than the methyl group it couples with
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Congratulations!This is the end of the quiz
Return to the contents page
You can find some more advanced problems through the following link:http://sasc-specialists.ucdavis.edu/jim/118A/ProtonNMR.Probs.html