MASS SPECTROMETRY. Intro to Spectroscopy, 3 rd ed., Pavia et al. Mass Spec – Ionization.
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Transcript of MASS SPECTROMETRY. Intro to Spectroscopy, 3 rd ed., Pavia et al. Mass Spec – Ionization.
MASS SPECTROMETRY
MASS SPECTROMETRY
(m a in lib ) Eth yl A c e ta te10 20 30 40 50 60 70 80 90 100
0
50
100
1529
43
45 6170
73 88
O
O
(m a in lib ) 1,6-He p ta d ie n e -3,5-d io n e , 1,7-b is(4-h yd ro xy-3-m e th o xyp h e n yl)-10 40 70 100 130 160 190 220 250 280 310 340 370
0
50
100
15 28 39 51 6577
89103
137
177
190
203
217 232 272
298 320
350 368
O
O
O
HO
O
O H
Intro to Spectroscopy, 3rd ed., Pavia et al.
Mass Spec – Ionization
Table 8.2, p 399 Intro to Spectroscopy, 3rd ed., Pavia et al.
Mass Spec – Molecular Formula
Table 8.3, p 401 Intro to Spectroscopy, 3rd ed., Pavia et al.
Mass Spec – Molecular Formula
(m a in lib ) Pro p yla m in e10 15 20 25 30 35 40 45 50 55 60 65 70
0
50
100
28
30
31 3941
4359
NH2
(m a in lib ) Be n ze n e , n itro -10 20 30 40 50 60 70 80 90 100 110 120 130
0
50
100
30 39
51
63
6574
77
93
107
123O
N
O
Mass Spec – Molecular Formula
(m a in lib ) Be n zo n itrile20 30 40 50 60 70 80 90 100 110
0
50
100
26 39
50
63
76
99
103
N
Mass Spec – Molecular Formula
Unknown: Contains C, H and one other element. Determine the MF and propose a structure.
(m a in lib ) Be n zyl c h lo rid e20 30 40 50 60 70 80 90 100 110 120 130 140
0
50
100
3945 51
65
91
126
C l
Table 8.6, p 403 Intro to Spectroscopy, 3rd ed., Pavia et al.
Mass Spec – Molecular Formula
(m a in lib ) Pro p a n e , 1-b ro m o -10 20 30 40 50 60 70 80 90 100 110 120 130
0
50
100
15
27
2939
41
43
93 107122
Br
Mass Spec – Molecular Formula
Unknown: Contains C, H and one other element. Determine the MF and propose a structure.
(m a in lib ) Be n ze n e , c h lo ro -20 30 40 50 60 70 80 90 100 110 120 130
0
50
100
3851
56 75
77
112
114
C l
Mass Spec – Fragmentation
Mass Spec – Fragmentation
Appendices p A39-A44, Intro to Spectroscopy, 3rd ed., Pavia et al.
Mass Spec – Functional Groups
Intro to Spectroscopy, 3rd ed., Pavia et al., p. 406
(m a in lib ) He xa n e0 10 20 30 40 50 60 70 80 90 100
0
50
100
15
27
29
39
41
43
57
71
86
(m a in lib ) Pe n ta n e , 2-m e th yl-0 10 20 30 40 50 60 70 80 90 100
0
50
100
15
27
39
43
57
71
86
Mass Spec – Alkanes
(m a in lib ) 1-He xe n e10 20 30 40 50 60 70 80 90 100
0
50
100
27
29
39
41
53
56
67
6984
(m a in lib ) 2-He xe n e10 20 30 40 50 60 70 80 90 100
0
50
100
15
29 39
42
53
55
67
69
84
Mass Spec – Alkenes
(m a in lib ) 1-He p tyn e10 20 30 40 50 60 70 80 90 100 110
0
50
100
27
29
39
41
51
55
57
65
67
79
81
95
(m a in lib ) 2-He p tyn e10 20 30 40 50 60 70 80 90 100 110
0
50
100
15
27
29
39
41
43
51
54
65
67
77
79
81
91
96
(m a in lib ) 3-He p tyn e10 20 30 40 50 60 70 80 90 100 110
0
50
100
15
27
29
39
41
51
53
55
63
65
67
77
79
81
91
96
Mass Spec – Alkynes
(m a in lib ) Eth ylb e n ze n e10 20 30 40 50 60 70 80 90 100 110 120
0
50
100
15 2739
51 65 77
91
106
(m a in lib ) o -Xyle n e10 20 30 40 50 60 70 80 90 100 110 120
0
50
100
2739
4351 65
74
77
91
103
106
(m a in lib ) Be n ze n e , 1,3-d im e th yl-10 20 30 40 50 60 70 80 90 100 110 120
0
50
100
1527
39
41
5165
74
77
91
103
106
(m a in lib ) p -Xyle n e10 20 30 40 50 60 70 80 90 100 110 120
0
50
100
2739 51 65
74
77
91
103
106
Mass Spec – Aromatic Hydrocarbons
(m a in lib ) Be n ze n e , b u tyl-10 20 30 40 50 60 70 80 90 100 110 120 130 140 150
0
50
100
27 3943
51 63
6578
89
91
105115
134
MS – Aromatic Hydrocarbons
(m a in lib ) Be n ze n e , b u tyl-10 20 30 40 50 60 70 80 90 100 110 120 130 140 150
0
50
100
27 3943
51 63
6578
89
91
105115
134
MS – Aromatic Hydrocarbons McLafferty Rearrangement
Intro to Spectroscopy, 3rd ed., Pavia et al., p. 416
(m a in lib ) 1-He xe n e10 20 30 40 50 60 70 80 90 100
0
50
100
27
29
39
41
53
56
67
6984
McLafferty ion
McLafferty ion
(m a in lib ) Be n ze n e , p ro p yl-
10 20 30 40 50 60 70 80 90 100 110 120 1300
50
100
27 39 5165 78
89
91
105
120
(m a in lib ) Be n ze n e , (1-m e th yle th yl)-10 20 30 40 50 60 70 80 90 100 110 120 130
0
50
100
15 2739
51
63 74
77
91
105
115
120
C9H12 - Unknown monosubstituted aromatic hydrocarbons.
MS – Aldehydes
(m a in lib ) Be n za ld e h yd e20 30 40 50 60 70 80 90 100 110 120
0
50
100
27 39
51
6374
77105
O
(m a in lib ) He xa n a l10 20 30 40 50 60 70 80 90 100 110
0
50
100
15
27
39
41
44
53
56
67
7282
O
MS – Ketones
(m a in lib ) 2-Bu ta n o n e10 20 30 40 50 60 70 80
0
50
100
1527
29
39 42
43
4457
71
72
73
O
(m a in lib ) 2-He p ta n o n e10 20 30 40 50 60 70 80 90 100 110 120 130
0
50
100
15
2741
43
55
58
71
85 99 114
O
MS – Ketones:1-phenyl-1-butanone vs 1-phenyl-2-butanone
(m a in lib ) 1-Bu ta n o n e , 1-p h e n yl-10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160
0
50
100
27 39
51
55 65
77
91
105
120
133
148
O
(m a in lib ) 1-Ph e n yl-2-b u ta n o n e10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160
0
50
100
27
29
39 51
57
65
91
148
O
MS – Esters
(m a in lib ) M e th yl p ro p io n a te10 20 30 40 50 60 70 80 90 100
0
50
100
15
27
29
3139 42 45 55
57
59
88
O
O
(m a in lib ) Be n zo ic a c id , e th yl e ste r10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160
0
50
100
27 39 45
51
77
105
122
150
O
O
MS – Esters
(m a in lib ) Bu ta n o ic a c id , e th yl e ste r10 20 30 40 50 60 70 80 90 100 110 120 130
0
50
100
15
27
29
41
43
45
4755
60
71
73
88
101116
O
O
(m a in lib ) Bu ta n o ic a c id , m e th yl e ste r10 20 30 40 50 60 70 80 90 100 110
0
50
100
15
27
29
39
41
43
45
55
57
59
69
71
74
87
102
O
O
MS –EstersUnknown: C8H16O2 Propose a structure and draw structures for defining fragment ions
(m a in lib ) He xa n o ic a c id , e th yl e ste r0 10 20 30 40 50 60 70 80 90 100 110 120 130 140 150
0
50
100
15
27
29
39
41
43
45 55
60
73
88
99
115144
O
O
(m a in lib ) Be n ze n e b u ta n o ic a c id
10 20 30 40 50 60 70 80 90 100 110 120 130 140 150 160 170 1800
50
100
2739
45 5160 65
78
91
104
117146
164
O H
O
(m a in lib ) Bu ta n o ic a c id10 20 30 40 50 60 70 80 90 100
0
50
100
2739
4145
55
60
71
73
88
O H
O
MS – Carboxylic Acids
MS-Amines
(m a in lib ) 1-Bu ta n a m in e10 20 30 40 50 60 70 80
0
50
100
28
30
31 39 41 44 5673
NH2
(m a in lib ) 1-Bu ta n a m in e , N ,N -d im e th yl-10 20 30 40 50 60 70 80 90 100 110
0
50
100
15 30 42
58
101
N
(m a in lib ) A c e ta m id e , N -p h e n yl-20 30 40 50 60 70 80 90 100 110 120 130 140 150
0
50
100
2839
43
5166
77
93
135
NH O
(m a in lib ) N ,N -Dim e th ylb u tyra m id e10 20 30 40 50 60 70 80 90 100 110 120 130
0
50
100
15
18
27
39
44
58
69
72
87
100
115
O
N
MS - Amides
(m a in lib ) Pe n ta n a l, 2-m e th yl-10 20 30 40 50 60 70 80 90 100 110
0
50
100
15
2939
41
43
53
58
71
100
O
MS – Unknown Aldehyde
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