spin-spin splitting
DESCRIPTION
Spin-Spin Splitting. At higher resolution, we see that the -CH 2 and -CH 3 peaks are split: Why? shielding is also affected by nuclear spin orientations of protons on adjacent carbons. Let’s look at this in more detail!. Chemistry Department, University of Isfahan. - PowerPoint PPT PresentationTRANSCRIPT
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Spin-Spin Splitting
At higher resolution, we see that the -CH2 and -CH3 peaks are split:
Why?shielding is also
affected by nuclear spin
orientations of protons
on adjacent carbons
Chemistry Department, University of Isfahan
Let’s look at this in more detail!
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More Spin-Spin Splitting CH3 Protons
split by the spins of the 2 adjacent CH2 protons:
↑↑ ↓↑ ↓↑ ↓↓ 1 2 1
3 peaks CH2 Protons
split by the spins of the 3 adjacent CH3 protons:
↑↑↑ ↑↑↓ ↑↓↑ ↓↑↑ ↓↓↑ ↓↑↓ ↑↓↓ ↓↓↓ 1 3 3 1
4 peaksChemistry Department, University of Isfahan
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Quantifying Spin-Spin Splitting Spin-spin splitting is quantified by:
J: Coupling Constant J is reported in absolute units (frequency, Hz) and
is typically 1-20 Hz
J depends only on the electronic and steric
relationships between interacting nuclei
Thus, J is independent of spectrometer B0
Chemistry Department, University of Isfahan
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More on Spin-Spin More on Spin-Spin SplittingSplitting
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Chemistry Department, University of Isfahan
Spin-Spin Coupling Spin-Spin Coupling Nuclei experiencing the same chemical environment or Nuclei experiencing the same chemical environment or
chemical shift are called equivalent. chemical shift are called equivalent. Those nuclei experiencing different environment or Those nuclei experiencing different environment or
having different chemical shifts are nonequivalent. having different chemical shifts are nonequivalent. Nuclei which are close to one another exert an influence Nuclei which are close to one another exert an influence
on each other's effective magnetic field. on each other's effective magnetic field. This effect shows up in the NMR spectrum when the This effect shows up in the NMR spectrum when the
nuclei are nonequivalent. nuclei are nonequivalent. If the distance between non-equivalent nuclei is less If the distance between non-equivalent nuclei is less
than or equal to three bond lengths, this effect is than or equal to three bond lengths, this effect is observable. This effect is called spin-spin coupling or J observable. This effect is called spin-spin coupling or J couplingcoupling. .
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Chemistry Department, University of Isfahan
Spin-Spin Coupling Spin-Spin Coupling Consider A and B, which are three bonds away from one Consider A and B, which are three bonds away from one
another in a molecule. another in a molecule. The spin of each nucleus can beThe spin of each nucleus can be
either aligned with the external field either aligned with the external field
the fields are N-S-N-S, called spin upthe fields are N-S-N-S, called spin up
or opposed to the external field or opposed to the external field
The fields are N-N-S-S, called spin down The fields are N-N-S-S, called spin down
The magnetic field at nucleus A will be either greater than B0 or less than B0 by a constant amount due to the influence of nucleus B.
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Chemistry Department, University of Isfahan
Spin-Spin Coupling Spin-Spin Coupling The NMR spectrum for nuclei A and B reflects the splittings The NMR spectrum for nuclei A and B reflects the splittings
observed in the energy level diagram. observed in the energy level diagram. The A absorption line is split into 2 absorption lines centered The A absorption line is split into 2 absorption lines centered
on on AA, and the B absorption line is split into 2 lines centered , and the B absorption line is split into 2 lines centered
on on BB. .
The distance between two split absorption lines is called the The distance between two split absorption lines is called the J coupling constant or the spin-spin splitting constant and is J coupling constant or the spin-spin splitting constant and is a measure of the magnetic interaction between two nuclei. a measure of the magnetic interaction between two nuclei.
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Chemistry Department, University of Isfahan
Spin-Spin Coupling Spin-Spin Coupling For the next example, consider a molecule with For the next example, consider a molecule with
three spin 1/2 nuclei, one type A and two type B. three spin 1/2 nuclei, one type A and two type B.
The type B nuclei are both three bonds away from The type B nuclei are both three bonds away from the type A nucleus. the type A nucleus.
The magnetic field at the A nucleus has three The magnetic field at the A nucleus has three possible values due to four possible spin possible values due to four possible spin configurations of the two B nuclei. configurations of the two B nuclei.
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Chemistry Department, University of Isfahan
Spin-Spin Coupling Spin-Spin Coupling The magnetic field at a B nucleus has two possible values.The magnetic field at a B nucleus has two possible values.
The energy level diagram for this molecule has six states or The energy level diagram for this molecule has six states or levels because there are two sets of levels with the same levels because there are two sets of levels with the same energy.energy.
Energy levels with the same energy are said to be Energy levels with the same energy are said to be degenerate. The vertical lines represent the allowed degenerate. The vertical lines represent the allowed transitions or absorptions of energy. transitions or absorptions of energy.
Note that there are two lines drawn between some levels Note that there are two lines drawn between some levels because of the degeneracy of those levels. because of the degeneracy of those levels.
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Chemistry Department, University of Isfahan
Spin-Spin Coupling Spin-Spin Coupling The resultant NMR spectrum is depicted in the animation The resultant NMR spectrum is depicted in the animation
window. window.
Note that the center absorption line of those centered at Note that the center absorption line of those centered at AA is is
twice as high as the either of the outer two. twice as high as the either of the outer two. This is because there were twice as many transitions in the This is because there were twice as many transitions in the
energy level diagram for this transition. The peaks at energy level diagram for this transition. The peaks at BB are are
taller because there are twice as many B type spins than A taller because there are twice as many B type spins than A type spins. type spins.
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Chemistry Department, University of Isfahan
Spin-Spin Coupling Spin-Spin Coupling The complexity of the splitting pattern in a spectrum The complexity of the splitting pattern in a spectrum
increases as the number of B nuclei increases. The increases as the number of B nuclei increases. The following table contains a few examples. following table contains a few examples.
Configuration Peak Ratios
A 1
AB 1:1
AB2 1:2:1
AB3 1:3:3:1
AB4 1:4:6:4:1
AB5 1:5:10:10:5:1
AB6 1:6:15:20:15:6:1
This series is called Pascal's triangle and can be calculated from the coefficients of the expansion of the equation:
(x+1)n
where n is the number of B nuclei in the above table.
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Chemistry Department, University of Isfahan
Spin-Spin Coupling Spin-Spin Coupling When there are two different types of nuclei three bonds When there are two different types of nuclei three bonds
away there will be two values of away there will be two values of JJ, one for each pair of , one for each pair of nuclei. nuclei.
By now you get the idea of the number of possible By now you get the idea of the number of possible configurations and the energy level diagram for these configurations and the energy level diagram for these configurations, so we can skip to the spectrum. configurations, so we can skip to the spectrum.
In the following example In the following example JJABAB is greater than is greater than JJBCBC..
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Effects of Magnetic Field on Spectrum?
J:unaffected
δ:unaffected
Resolution:
(Hz / ppm)
∝ B0
Chemistry Department, University of Isfahan
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CH3CH2OHA ( ) + HOHB ( ) CH3CH2OHB ( ) + HOHA ( )
CH3CH2OHA ( ) + HOHB ( ) CH3CH2OHB ( ) + HOHA ( )
CH3CH2OHA ( ) + HOHB ( ) CH3CH2OHB ( ) + HOHA ( )
CH3CH2OHA ( ) + HOHB ( ) CH3CH2OHB ( ) + HOHA ( )
Chemical Exchange
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Chemistry Department, University of Isfahan
NMR SolventsAcetone CD3COCD3
Chloroform CDCl3
Dichloromethane CD2Cl2
Benzene C6D6
Water D2O
N,N-Dimethylformamide (DMF) (CD3)2NCDO
Dimethyl Sulfoxide (DMSO) CD3SOCD3
Ethanol CD3CD2OD
Methanol CD3OD
Tetrehydrofuran (THF) C4D8O
Toluene C6D5CD3
Pyridine C5D5N
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1313C-NMR SpectroscopyC-NMR Spectroscopy Each nonequivalent Each nonequivalent 1313C gives a different C gives a different
signalsignal A A 1313C is split by the C is split by the 11H bonded to it H bonded to it
according to the (n + 1) rule according to the (n + 1) rule Coupling constants of 100-250 Hz are Coupling constants of 100-250 Hz are
common, which means that there is often common, which means that there is often significant overlap between signals, and significant overlap between signals, and splitting patterns can be very difficult to splitting patterns can be very difficult to determinedetermine
The most common mode of operation of a The most common mode of operation of a 1313C-NMR spectrometer is a hydrogen-C-NMR spectrometer is a hydrogen-decoupled modedecoupled mode
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1313C-NMR SpectroscopyC-NMR Spectroscopy In a hydrogen-decoupled mode, a sample is In a hydrogen-decoupled mode, a sample is
irradiated with two different radio irradiated with two different radio frequenciesfrequencies one to excite all one to excite all 1313C nucleiC nuclei a second is a broad spectrum of frequencies that a second is a broad spectrum of frequencies that
causes all hydrogens in the molecule to undergo causes all hydrogens in the molecule to undergo rapid transitions between their nuclear spin rapid transitions between their nuclear spin statesstates
On the time scale of a On the time scale of a 1313C-NMR spectrum, C-NMR spectrum, each hydrogen is in an average or each hydrogen is in an average or effectively constant nuclear spin state, with effectively constant nuclear spin state, with the result that the result that 11H-H-1313C spin-spin interactions C spin-spin interactions are not observed; they are decoupledare not observed; they are decoupled
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Carbon – 13 shiftsCarbon – 13 shifts
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Continuous-Wave NMRContinuous-Wave NMR
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Dr. S. M. Condren
Continuous-Wave NMRContinuous-Wave NMR““Block diagram of Continuous-Wave Block diagram of Continuous-Wave NMR.”NMR.”
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Dr. S. M. Condren
Instrumentation - CW-Instrumentation - CW-NMRNMR
R-F transmitterR-F transmitter
R-F receiver & detectorR-F receiver & detector
samplesample
magnetmagnet
recorderrecorder
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Dr. S. M. Condren
Instrumentation CW-Instrumentation CW-NMRNMR
R-F transmitterR-F transmitter irradiate sample with resonant radio irradiate sample with resonant radio
frequencyfrequency less than 1 W output but reproducible less than 1 W output but reproducible
to 1 part in 10to 1 part in 1099
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Dr. S. M. Condren
Instrumentation CW-Instrumentation CW-NMRNMR
R-F receiver & detectorR-F receiver & detector detect the radio frequency detect the radio frequency amplify 10amplify 105 5 timestimes integratorintegrator
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Dr. S. M. Condren
Instrumentation CW-Instrumentation CW-NMRNMR
sweep generator => sweep coilsweep generator => sweep coil modify the applied magnetic fieldmodify the applied magnetic field ““scans” through slight (ppm) scans” through slight (ppm)
changes in magnetic field which changes in magnetic field which produces variations in position of produces variations in position of resonant frequencyresonant frequency
modifies magnetic field to give modifies magnetic field to give spectrumspectrum
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Dr. S. M. Condren
Instrumentation CW-Instrumentation CW-NMRNMR
samplesample sample suspended between pole sample suspended between pole
faces of magnetfaces of magnet sample is spunsample is spun
air driven turbine - average out effects air driven turbine - average out effects of in homogeneities in the fieldof in homogeneities in the field
5 mm O.D. tube5 mm O.D. tube
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Dr. S. M. Condren
Instrumentation CW-Instrumentation CW-NMRNMR
magnetmagnet causes the nuclear spin states to causes the nuclear spin states to
splitsplit allows sample to absorb energy allows sample to absorb energy
equal to the difference between spin equal to the difference between spin statesstates
most expensive componentmost expensive component must be reproducible & must be reproducible &
homogeneoushomogeneous
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Dr. S. M. Condren
MagnetsMagnets
type of magnettype of magnet max. field max. field strengthstrength
permanentpermanent 14,092 G 14,092 G
conventional electromagnetconventional electromagnet 23,49023,490
superconducting solenoidssuperconducting solenoids<169,000<169,000
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Dr. S. M. Condren
MagnetsMagnets
type of magnettype of magnet max. field max. field strengthstrength
permanentpermanent 1.41 T 1.41 T
conventional electromagnetconventional electromagnet 2.35 2.35
superconducting solenoidssuperconducting solenoids<16.9 <16.9
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Dr. S. M. Condren
Sample HandlingSample Handling
solutionsolution solvents should be free of hydrogensolvents should be free of hydrogen
deuterated solvents used where necessarydeuterated solvents used where necessary should contain standardshould contain standard
most commonly tetramethyl silane (TMS)most commonly tetramethyl silane (TMS) TMS signal position set at 0 ppmTMS signal position set at 0 ppm other peaks relative to TMSother peaks relative to TMS
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Dr. S. M. Condren
FT-NMRFT-NMR
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Dr. S. M. Condren
Components of FT Components of FT SpectrometersSpectrometers
"Block diagram "Block diagram of a Fourier of a Fourier transform NMR transform NMR spectrometer."spectrometer."
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Dr. S. M. Condren
MagnetMagnet
in the past, electromagnets or in the past, electromagnets or superconducting solenoidssuperconducting solenoids
today, permanent magnets or today, permanent magnets or superconducting solenoidssuperconducting solenoids
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Dr. S. M. Condren
Locking the Magnetic Locking the Magnetic FieldField
field/frequency lock systemfield/frequency lock system reference nucleus is continuously reference nucleus is continuously
irradiated and monitored at a frequency irradiated and monitored at a frequency corresponding to its resonance corresponding to its resonance maximum at the rated field strength of maximum at the rated field strength of the magnetthe magnet
provided by deuterium in the solvent, provided by deuterium in the solvent, with second transmitter coil set to the with second transmitter coil set to the frequency for deuteriumfrequency for deuterium
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Dr. S. M. Condren
ShimmingShimming
coils which provide some changes in the coils which provide some changes in the magnetic field by carefully controlling magnetic field by carefully controlling the current flowing through the coilsthe current flowing through the coils
used to correct for inhomogeneities of used to correct for inhomogeneities of magnetmagnet
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Dr. S. M. Condren
Sample SpinningSample Spinning
sample is spun along its longitudinal sample is spun along its longitudinal axis to counteract some of the field axis to counteract some of the field inhomogeneitiesinhomogeneities
"A minor disadvantage of spinning is "A minor disadvantage of spinning is that the magnetic field is modulated at that the magnetic field is modulated at the spinning frequency, which may lead the spinning frequency, which may lead to to sidebandssidebands on each side of absorption on each side of absorption peaks?"peaks?"
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Dr. S. M. Condren
Sample ProbeSample Probe1.1. holds sample in the magnetic holds sample in the magnetic
fieldfield
2.2. spins the samplespins the sample
3.3. houses the coil or coils that houses the coil or coils that permit excitation and detection of permit excitation and detection of the NMR signal and preamp the NMR signal and preamp
4.4. coil for lockingcoil for locking
5.5. coil for decouplingcoil for decoupling
6.6. variable temperature capabilityvariable temperature capability
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Dr. S. M. Condren
Transmitter/Receiver Transmitter/Receiver CoilsCoils
early instruments, separate coils, at early instruments, separate coils, at right angles to each otherright angles to each other
FT-NMRs, normally same coilFT-NMRs, normally same coil
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Dr. S. M. Condren
Pulse GeneratorPulse Generator
1. a continuous crystal oscillator1. a continuous crystal oscillator
2.2. a gate to switch the pulse on a gate to switch the pulse on and offand off
3.3. a power amplifier to amplify a power amplifier to amplify the pulse to perhaps 50 - 100 Wthe pulse to perhaps 50 - 100 W
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Dr. S. M. Condren
Receiver SystemReceiver System
nanovolt - microvolt signal amplified to nanovolt - microvolt signal amplified to 10 V 10 V
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Dr. S. M. Condren
Detector and Data Detector and Data Processing SystemProcessing System
high-frequency radio signal converted high-frequency radio signal converted to audio-frequency signal to digitizedto audio-frequency signal to digitized
carrier signal with superimposed NMR carrier signal with superimposed NMR signal, 10 ppm PMR spectrum at 270 signal, 10 ppm PMR spectrum at 270 MHz would have a frequency range of MHz would have a frequency range of 2700 Hz2700 Hz
subtract the carrier signal from NMR subtract the carrier signal from NMR signalsignal
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Dr. S. M. Condren
Sampling the Audio Sampling the Audio SignalSignal
digitize signal, must sample signal digitize signal, must sample signal at least twice per cycleat least twice per cycle
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Dr. S. M. Condren
Single-Channel Single-Channel DetectionDetection
disadvantage, does not know if disadvantage, does not know if difference between carrier signal difference between carrier signal and NMR signal is positive or and NMR signal is positive or negative, can produce a false negative, can produce a false signalsignal
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Dr. S. M. Condren
Quadrature Detection Quadrature Detection SystemsSystems
NMR signal is split and fed to two NMR signal is split and fed to two identical detectorsidentical detectors in one detector the signal is treated in in one detector the signal is treated in
the normal manner, carrier signal the normal manner, carrier signal subtracted from NMR signal for subtracted from NMR signal for digitizingdigitizing
in the second detector the carrier in the second detector the carrier signal is altered 90signal is altered 9000 before subtraction before subtraction
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Dr. S. M. Condren
Quadrature Detection Quadrature Detection SystemsSystems
the two audio signal are the same the two audio signal are the same except for phase, the first produces a except for phase, the first produces a cosine wave while the second produces cosine wave while the second produces a sine wavea sine wave
the two signals are digitized, the two signals are digitized, transformed separately into frequency transformed separately into frequency domain signals and combined to domain signals and combined to produce the spectrumproduce the spectrum
folded signal disappears because it is folded signal disappears because it is of opposite sign in the cosine and sine of opposite sign in the cosine and sine wave formswave forms