NMR Phenomenon. Nuclear Magnetic Resonance. µ A spinning charged particle generates a magnetic field.
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1 NMR Phenomenon Nuclear Magnetic Resonance µ A spinning charged particle generates a magnetic field. A nucleus with a spin angular momentum will generate a magnetic moment (μ). If these tiny magnets are placed in an applied magnetic field (Bo), they will adopt two different states - one aligned with the field and one aligned against the field. The energy difference between these two states is what we are observing with NMR. B 0 1
2 Nuclear Spin States aligned against B 0 E Energy difference between the states at a particular magnet strength. In the R f range of the EM Spectrum. aligned with B 0 B 0 When EM waves at this energy are directed at the nuclei - it will absorb. Spins will flip from lower energy to higher energy. At that energy, nuclei are In Resonance. 2
3 NMR Active Nuclei Many nuclei are NMR Active Spin Quantum Number I I = ½; I = ½ 12, I = 0 -- an t be observed ther nuclei that are NMR active 2 (D), 14 N, 19 F, 31 P 3
4 NMR Instrumentation 4
5 Magnetic Resonance Imaging NMR is the basis for MRI 5
6 To summarize µ A spinning charged particle generates a magnetic field. A nucleus with a spin angular momentum will generate a magnetic moment (m). When placed in a magnetic field (Bo), they will adopt two different states - one aligned with the field and one aligned against the field. B 0 aligned against B 0 E Energy difference between the states at a particular magnet strength. In the R f range of the EM Spectrum. aligned with B 0 B 0 6
7 Methyl Acetate - Proton NMR 3 3 7
8 Methyl Acetate - arbon NMR 3 3 solvent 8
9 Electronic Shielding - Local Environments B local µ B effective = B 0 - B local Actual magnetic field felt by the nucleus B 0 B effective 9
10 Methyl Acetate - Proton NMR
11 Methyl Acetate - arbon NMR 3 3 solvent 11
12 hemical Shift The difference in resonance frequency of a nuclei relative to a standard Most Shielded Relatively Inert Volatile 3 3 Si 3 Resonance of standard is set to 0 3 TMS TetraMethylSilane 12
13 NMR Scale X-Axis - frequency axis NMR Spectrum Low Field Little electron shielding (more electron withdrawing groups) igh Field More electron shielding (less electron withdrawing groups) peaks measured as a shift (in z) away from TMS Reference TMS 10 z 0 13
14 Different Spectrometer Frequencies Each specific instrument has it s own magnetic field strength - resonace occurs at different frequencies. aligned against B Mz NMR 300 Mz NMR E B 0 Energy difference between the states at a particular magnet strength. In the R f range of the EM Spectrum. aligned with B 0 Reference TMS 300 z 100 z 0 14
15 Standard Scale δ = ppm = hemical Shift from TMS (z) Spectrometer Frequency (Mz) 100 Mz NMR 300 Mz NMR 100 z 100 Mz 300 z 300 Mz = 1.0 ppm = 1.0 ppm Reference TMS 1.0 ppm 0 15
16 NMR Scale 16
17 13 NMR Difficult - arbon 13 only 1.1% of all carbon. Number of different carbons Functional Group Regions 13 NMR R R R R R NR 2 N X δ ppm 17
18 13 NMR 18
19 Symmetry Symmetry in molecules can make carbons hemically Equivalent l 3 3 same electronic environment Br 19
20 Symmetry Some molecules have more than one mirror plane
21 Symmetry
22 Symmetry
23 Substitution of arbon The intensity of the peaks roughly correlates with the number of hydrogens on the carbon. 23
24 13 NMR Regions 13 NMR R R R R R NR 2 N X δ p 24
25 Bromooctanol Br 25
26 Bromooctanal Br 26
27 Alanine Me-Ester l 3 3 N 3 l 27
28 Alaninol 3 N 2 28
29 Alaninol - phthalimide 3 N 29
30 DEPT-13 A - normal 13 B - carbons only - dd # up (3 and ) Even # down (2) 30
31 Example from 13.7 l K ethanol or 31
32 A Real Example N N R N N N N 2, Pd/ 2, Pd/ N N R N N N In the alkane region there would only be 4 peaks due to symmetry N In the alkane region there would be 6 different peaks 32
33 The Answer Is... N N N N 33
34 Proton NMR Number of chemically different hydrogens Relative Ratios of protons (peak size) ow many neighboring hydrogens hemical shifts and functional groups 34
35 Proton Equivalency omotopic Diastereotopic 3 3 replace 's - same Enantiotopic 3 3 l replace 's - diastereomers X X X 3 3 X l 3 3 l replace 's - enantiomers X X
36 Proton NMR Scale Range 0-10 ppm 1 NMR X δ ppm 36
37 NMR orrelation hart Typical NMR hemical Shifts Functional Group Type 1 hemical Shift (ppm) 13 hemical Shift (ppm) Alkane Allylic or next to carbonyl X next to halogen or alcohol next to oxygen of an ester vinylic aromatic X aldehyde alcohol carbonyl of ester, amide, or carboxylic acid (X =, N) varies widely will exchange with D 2 N/A N/A carbonyl of ketone or aldehyde N/A
38 Methyl Acetate 3 3 Area under peak corresponds to the number of s for that resonance 38
39 Triphenyl Methanol 39
40 Ethyl Acetate
41 Spin Spin Splitting Protons on adjacent carbons also have an effect Resonances will split into n+1 number of peaks a b 1 NMR (without coupling) a b b 1 NMR (with coupling) J J 41
42 Spin Spin Splitting Two hydrogens split neighbors into a triplet a b b 1 NMR (without coupling) a b b 1 NMR (with coupling) J J J 1 : 2 : 1 42
43 Spin Spin Splitting Every splitting can be broken down into a series of doublets a b b 1 NMR (without coupling) a b J NMR (with coupling) J J 1 : 2 : 1 43
44 Spin Spin Splitting Three neighbors - Quartet a b b b 1 NMR (without coupling) a b b 1 NMR (with coupling) J J J J 1 1 : 3 : 3 :
45 igher Spin Spin Splitting Pascal s Triangle b a b b b b b a will split into 7 peaks 64 different combinations of 6 spins singlet 1 doublet triplet quartet quintet sextet septet
46 Summary of Spin Spin Splitting Proton resonance split into n+1 number of peaks Relative ratio of peaks depends on number of spin states of the neighbors. Adjacent protons will couple with the same coupling constant. Protons farther away usually do not couple. hemically equivalent protons cannot couple (eg. l l)
47 Doublet Splitting 3 Methyl sees 1 neighbor, Methine sees 3 3 N 3 l 47
48 Ethanol Note that the (and N) usually don t couple. 48
49 1,1,2-Trichloroethane 49
50 2-Bromopropane 50
51 Butanone 51
52 para-methoxypropiophenone 52
53 Toluene Sometimes peaks overlap 53
54 innamaldehyde Multiple oupling 54
55 Spin Spin Splitting Every splitting can be broken down into a series of doublets a b b 1 NMR (without coupling) a b J NMR (with coupling) J J 1 : 2 : 1 55
56 oupling with the same J a J a-b = 5 z J a-c = 5 z b a c coupling with b 5 coupling with c
57 oupling with different J values a J a-b = 5 z J a-c = 10 z coupling with b 5 b a c coupling with c a coupling with c 10 coupling with b
58 innamaldehyde Multiple oupling J 1-2 = 6 z, 2-3 = 12 z 58
59 innemaldehyde 59
60 Multiple oupling - Identical J a J a-b = 5 z J a-c = 5 z b a c coupling with b 5 c coupling with c coupling with c
61 Multiple oupling - Different J J a-b = 10 z J a-c = 5 z a b a c c coupling with c 5 coupling with c coupling with b
62 Nitropropane 62
63 Strategies for Determining Unknows Given the Molecular Formula - calculate degrees of unsaturation. Identify functional groups Identify pieces of the structure Put the pieces together in a reasonable way Double check that your structure matches all the data given. 63
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