The NMR Spectrum - 13 C. NMR Spectroscopy. Spin-Spin Coupling 13 C NMR. A comparison of two 13 C NMR Spectra. H Coupled (undecoupled) H Decoupled

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Transcription:

Spin-Spin oupling 13 NMR A comparison of two 13 NMR Spectra 1 oupled (undecoupled) 1 Decoupled 1

Proton Decoupled 13 NMR 6. To simplify the 13 spectrum, and to increase the intensity of the observed signals, a decoupler is used to remove the spin effects of the 1 nucleis 7. A second RF generator irradiates at the 1 resonance frequency causing the saturation effectively averaging all their spin states to zero 1 channel- 13 channel 13 n pulse 13 FID 2

Nuclear Overhauser Effect (NOE) 1. A phenomenon observed with proton-decoupled 13 -NMR is that the intensity of the signal for a given 13 increases versus the proton-coupled spectrum roughly proportional to the number of protons attached 2. The degree of this signal enhancement is called the Nuclear Overhauser Enhancement (NOE) and is a heteronuclear effect 6. This effect is general, and appears anytime when one of two types of atoms is irradiated, while the spectrum of the other is observed In this case, while the 1 population is irradiated to saturation, the 13 is observed 3

Nuclear Overhauser Effect (NOE) 4. The effect can be a positive or negative one, but for the case of 1-13, the effect is positive 5. The maximum enhancement is given by: noe max = 1 (g irradiated ) 2 (g observed ) This value is what is added to the observed intensity in the coupled spectrum to give the intensity observed in the decoupled spectrum: total predicted intensity = 1 + NOE max 4

Nuclear Overhauser Effect (NOE) 6. For 1 13, noe = ½ (267.5/67.28) = 1.988 7. This indicates a maximum enhancement of almost 200% is possible 8. NOE operates in both directions 13 nuclei (if decoupled) would enhance the signal of 1 however, this signal would be weak due to the low prevelance of 13 9. Because NOE for 13 1 operates in the opposite direction (a rare nuclei always bound to an abundant one) it is a useful probe into structural assignments 10. The NOE effect is very short-ranged, falling off as 1/r 3 the distance between the nuclei 5

Nuclear Overhauser Effect (NOE) Origin of the effect Observe the following energy diagram: ere, we see an isolated two spin system between a single carbon and single hydrogen atom N 4 The effects of coupling are left out for simplicty N 3 N 2 Shown are the four combinations of spin states of these two nuclei, N 1-4 As expected, the two energy states where both are spin up or spin down are the lowest and highest energy states N 1 The mixed states are roughly degenerate in energy 6

Nuclear Overhauser Effect (NOE) Origin of the effect Quantum mechanics dictates that allowed transitions involve only one change of spin at a time single quantum transitions N 4 The allowed transitions are shown in red N 3 N 2 N 1 7

Nuclear Overhauser Effect (NOE) Origin of the effect Let s set the equilibrium population of the two degenerate states to be B The N 1 level would be lower than B by a small amount, d N 4 The N 4 level would be higher than B by a the same amount, d The signal for a 13 in this case would be proportional to d at equilibrium N 3 N 2 The two 13 transitions are N 1 N 2 and N 3 N 4 N 1 8

Nuclear Overhauser Effect (NOE) Origin of the effect When a decoupler is used, the 1 populations are disturbed from their equilibrium values Relaxation processes restore these disturbed populations to their equilibrium values One such process is a doublequantum transition, where both the and nuclei relax simultaneously (blue line) N 4 double N quantum 3 transition N 2 This leak in the upper state enhances the population of the lower energy state for carbon the excess population is larger and the signal intensifies N 1 9

Relaxation Processes 1. The generation of the FID from either 1 or 13 nuclei comes from the relaxation of the excess population from the excited to the ground equilibrium population in the magnetic field 2. There are two mechanisms for this relaxation: 3. T 1 process called spin-lattice relaxation or longitudinal here spins lose their energy by transferring it to the surroundings (lattice) as heat in the direction of the field 4. T 2 process called spin-spin relaxation here the spin is transferred to another nuclei in the plane in which the signal is detected It is an entropy process, and causes the signal of the proton population to lose phase with the other excited nuclei 10

Relaxation Processes 5. The importance of these two relaxation types is low for 1 NMR, the relaxation times are generally fast, and any information from them is usually lost 6. 13 has a long relaxation period and the effect of T 2 type decay is pronounced for a nuclei such as a quaternary carbon which has no adjacent nuclei capable of transferring spin to 7. Ipso, quaternary and carbonyl carbons have low intensities due to this effect since many hundreds of pulses are used to generate a 13 spectrum, the delay between pulses is often short for time constraints 8. These carbons therefore do not decay effectively before the next pulse, weakening the signal 11

DEPT Distortionless Enhancement by Polarization Transfer 1. This is the first advanced 1-D technique we will consider 2. As we just pointed out, the relaxation times for 13 are strongly a factor of T 2 processes where spin is transferred and the resulting signal shifts out of phase with what is being detected 3. If different pulse widths are applied in a 13 determination, the resulting phase shift (and signal intensity) will be different depending on how many 1 atoms the 13 can transfer its spin to 4. In a typical DEPT experiment, a 45, 90 and 135 pulse are applied successively to the sample and the results compared to the original carbon spectrum 12

DEPT Distortionless Enhancement by Polarization Transfer 5. At each pulse angle, a different effect is observed for quaternary, methine, methylene and methyl carbons: DEPT Pulse Sequence methyl methylene methine quaternary DEPT-45 Positive peak Positive peak Positive peak Not observed DEPT-90 No obs. peak No obs. peak Positive peak Not observed DEPT-135 Positive peak Negative Peak Positive Peak Not observed 13

DEPT Distortionless Enhancement by Polarization Transfer 6. The spectra are typically illustrated together to allow the operator to find the substitution of each carbon in the spectrum: O DEPT 135 DEPT 90 DEPT 45 14

Integration 1. For reasons of long relaxation times, NOE, and low population abundance, 13 spectra are not integrated 2. For 1 NMR most nuclei relax in a second or two, the intensity of the signal is only proportional to the observation of the excess population 3. Relaxation times for 13 are prohibitively long given the number of pulses needed to generate a spectrum signal intensity, already low is more a factor of T 1, T 2 and NOE 15