3 Use of Mass Spectra to Obtain Structural Information
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1 3 Use of Mass Spectra to Obtain Structural Information 1
2 Mass Spectrometry One of the most sensitive and versatile analytical tools More sensitive than other spectroscopic methods (e.g. IR spectroscopy) Only a microgram or less of materials is required for the analysis 2
3 Mass Spectrometry In a mass spectrometric analysis, it involves: 1. the conversion of molecules to ions 2. separation of the ions formed according to their mass-to-charge (m/e) ratio m is the mass of the ion in atomic mass units and e is its charge 3
4 Mass Spectrometry Finally, the number of ions of each type (i.e. the relative abundance of ions of each type) is determined The analysis is carried out using a mass spectrometer 4
5 Mass Spectrometry Components of a mass spectrometer 5
6 Mass Spectrometry In the vaporization chamber, the sample is heated until it vaporizes changes to the gaseous state 6
7 Mass Spectrometry The molecules in the gaseous state are bombarded with a beam of fast-moving electrons Positively-charged ions called the molecular ions are formed One of the electrons of the molecule is knocked off 7
8 Mass Spectrometry Molecular ions are sometimes referred to as the parent ion 8
9 Mass Spectrometry!one of the electrons is removed from the molecules during the ionization process the molecular ion contains a single unpaired electron the molecular ion is not only a cation, it is also a free radical 9
10 Mass Spectrometry e.g. if a molecule of methanol (CH 3 OH) is bombarded with a beam of fast-moving electrons the following reaction will take place: 10
11 Mass Spectrometry The molecular ions formed in the ionization chamber are energetically unstable undergo fragmentation Fragmentation can take place in a variety of ways depend on the nature of the particular molecular ion 11
12 Mass Spectrometry The way that a molecular ion fragments give us highly useful information about the structure of a complex molecule 12
13 Mass Spectrometry The positively charged ions formed are then accelerated by electric field and deflected by magnetic field causes the ions to arrive the ion detector The lighter the ions, the greater the deflection 13
14 Mass Spectrometry Positively charged ions of higher charge have greater deflection Ions with a high m/e ratio are deflected to smaller extent than ions with a low m/ e ratio 14
15 Mass Spectrometry In the ion detector, the number of ions collected is measured electronically The intensity of the signal is a measure of the relative abundance of the ions with a particular m/e ratio 15
16 Mass Spectrometry The spectrometer shows the results by plotting a series of peaks of varying intensity each peak corresponds to ions of a particular m/e ratio The graph obtained is known as a mass spectrum 16
17 Mass Spectrum Generally published as bar graphs. 17 Mass spectrum of methanol
18 Mass Spectrum Corresponding ion m/e ratio H 15 H C 29 H 31 CH 32 Interpretation of the mass spectrum of methanol 18
19 Formation of Fragments The molecular ions formed in the ionization chamber are energetically unstable Some of them may break up into smaller fragments Called the daughter ions 19
20 Formation of Fragments These ionized fragments are accelerated and deflected by the electric field and magnetic field Finally, they are detected by the ion detector and their m/e ratios are measured explains why there are so many peaks appeared in mass spectra 20
21 Formation of Fragments 21 Mass spectrum of methanol The peak at m/e 31 the most intense peak Arbitrarily assigned an intensity of 100% Called the base peak Corresponds to the most common ion formed
22 Formation of Fragments The peak at m/e 31 corresponds to the ion H 2 C = OH + formed by losing one hydrogen atom from the molecular ion 22
23 Formation of Fragments The ion H 2 C = OH + is a relatively stable ion!the positive charge is not localized on a particular atom it spreads around the carbon and the oxygen atoms to form a delocalized system 23
24 Formation of Fragments The peak at m/e 29 corresponds to the ion HC O + formed by losing two hydrogen atoms from the ion H 2 C = OH + 24
25 Formation of Fragments The ion HC O + has two resonance structures: 25
26 Formation of Fragments The peak at m/e 15 corresponds to the ion H 3 C + formed by the breaking of the C O bond in the molecular ion 26
27 Formation of Fragments Mass spectrum of pentan-3-one 27
28 Formation of Fragments Corresponding ion m/e ratio CH 29 CH 57 CH 86 Interpretation of the mass spectrum of pentan-3-one 28
29 Formation of Fragments The fragmentation pattern of pentan-3-one is summarized below: 29
30 Fragmentation Pattern 1. Straight-chain Alkanes Simple alkanes tend to undergo fragmentation by the initial loss of a CH 3 to give a peak at M 15 This carbocation can then undergo stepwise cleavage down the alkyl chain 30
31 1. Straight-chain Alkanes Take hexane as an example: 31
32 2. Branched-chain Alkanes Tend to cleave at the branch point more stable carbocations are formed 32
33 2. Branched-chain Alkanes e.g. 33
34 3. Alkyl-substituted Aromatic Hydrocarbons Undergo loss of a hydrogen atom or alkyl group yield the relatively stable tropylium ion Gives a prominent peak at m/e 91 34
35 3. Alkyl-substituted Aromatic Hydrocarbons e.g. 35
36 4. Aldehydes and Ketones Frequently undergo fragmentation by losing one of the side chains generate the substituted oxonium ion often represents the base peak in the mass spectra 36
37 4. Aldehydes and Ketones 37
38 5. Esters, Carboxylic Acids and Amides Often undergo cleavage that involves the breaking of the C X bond form substituted oxonium ions as shown below: (where X = OH, OR, NH 2, NHR, NR 2 ) 38
39 5. Esters, Carboxylic Acids and Amides For carboxylic acids and unsubstituted amides, characteristic peaks at m/e 45 and 44 are observed respectively 39
40 6. Alcohols In addition to the loss of a proton and the hydroxyl radical, alcohols tend to lose one of the α alkyl groups (or α hydrogen atoms) form oxonium ions 40
41 6. Alcohols For primary alcohols, the peak at m/e 31, 45, 59 or 73 often appears depends on what the R 1 group is 41
42 7. Haloalkanes Haloalkanes simply break at the C X bond 42
43 7. Haloalkanes In the mass spectra of chloroalkanes, two peaks, separated by two mass units, in the ratio 3 : 1 will be appeared 43
44 7. Haloalkanes In the mass spectra of bromoalkanes, two peaks, separated by two mass units, having approximately equal intensities will be appeared 44
45 45 The END
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