Qualitative Organic Analysis CH 351 Mass Spectrometry
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1 Qualitative Organic Analysis CH 351 Mass Spectrometry Bela Torok Department of Chemistry University of Massachusetts Boston Boston, MA
2 General Aspects Theoretical basis of mass spectrometry
3 Basic Instrumentation General Aspects
4 General Aspects - Ionization Methods Gas Phase Ionization Methods Electron Impact Ionization (EI) electron beam Chemical Ionization (CI) ionized molecules (CH 3+, or (CH 3 ) 3 C +
5 General Aspects - Ionization Methods Gas Phase Ionization Methods
6 General Aspects - Ionization Methods Desorption Ionization Methods Field Desorption Ionization (FD) emits ions fro surface Fast Atom Bombardment (FAB) high energy Xe or Ar atoms (liquid sample) Liquid Secondary Ionization Mass Spec. LSIMS Cs + ions Plasma Desorption Ionization fission product of 252 Cf Laser Desorption Ionization laser beam
7 Desorption Ionization Methods General Aspects - Ionization Methods
8 General Aspects - Ionization Methods Evaporative Ionization Methods Thermospray MS (TSMS) Electrospray MS (ESI-MS) heated capillary tube (outdated)
9 General Aspects - Ionization Methods The Nobel Prize in Chemistry 2002 John B. Fenn Koichi Tanaka Kurt Wüthrich
10 General Aspects - Ionization Methods The Nobel Prize in Chemistry 2002
11 General Aspects - Ionization Methods Evaporative Ionization Methods
12 General Aspects - Ionization Methods
13 General Aspects Mass Analyzers Magnetic Sector Mass Spectrometers
14 General Aspects Mass Analyzers Magnetic Sector Mass Spectrometers
15 General Aspects Mass Analyzers Quadrupole Mass Spectrometers
16 General Aspects Mass Analyzers Ion Trap Mass Spectrometers
17 General Aspects Mass Analyzers Time-of-Flight Mass Spectrometers
18 General Aspects Mass Analyzers MALDI TOF Mass Spectrometers Some common MALDI matrices at 337 nm. Matrix 2,5- Dihydroxybenz oic acid (DHB) 3,5-Dimethoxy- 4- hydroxycinnami c acid (sinapinic acid) α-cyano-4- hydroxycinnami c acid (CHCA) Application Peptides, proteins, lipids, and oligosaccarides Peptides, proteins, and glycoproteins Peptides, proteins, lipids, and oligonucleotides
19 General Aspects Mass Analyzers MALDI TOF Mass Spectrometers Ladder sequencing of the adrenocorticotropic hormone (ACTH) fragment utilizing the CPY dilution technique and MALDI linear DE-TOF-MS
20 General Aspects Mass Analyzers Tandem Mass Spectrometry
21 General Aspects Mass Analyzers Tandem Mass Spectrometry
22 General Aspects Mass Analyzers
23 General Aspects Interpretation of Mass Spectra The mass spectrum
24 The ionization General Aspects Interpretation of Mass Spectra
25 General Aspects Interpretation of Mass Spectra High Resolution Mass Spectra High resolution MS - molecular formula
26 General Aspects Interpretation of Mass Spectra M-2 peaks Peaks are commonly observed at m/z values two units below the m/z values of a carbocation, because the carbocation can lose two hydrogens
27 General Aspects Interpretation of Mass Spectra Fragmentation (EI only!!!)
28 General Aspects Interpretation of Mass Spectra Fragmentation (EI only!!!!)
29 General Aspects Interpretation of Mass Spectra Rearrangements McLafferty rearrangement
30 General Aspects Interpretation of Mass Spectra Mass Spectrum 2-Me-butane
31 General Aspects Interpretation of Mass Spectra Isotope Effects
32 General Aspects Interpretation of Mass Spectra Isotope Effects
33 General Aspects Interpretation of Mass Spectra Mass Spectrum 2-Cl-propane
34 General Aspects Interpretation of Mass Spectra Fragmentation 2-Cl-propane
35 Mass Spectra of the Common Classes of Compounds Hydrocarbons Alkanes - Large compounds show fairly similar spectra (M +!)
36 Mass Spectra of the Common Classes of Compounds Hydrocarbons Cycloalkanes
37 Mass Spectra of the Common Classes of Compounds Hydrocarbons Alkenes (olefins)
38 Mass Spectra of the Common Classes of Compounds Hydrocarbons Aromatics and alkylaromatics
39 Mass Spectra of the Common Classes of Compounds Alcohols
40 Mass Spectra of the Common Classes of Compounds Alcohols
41 Mass Spectra of the Common Classes of Compounds Alcohols
42 Mass Spectra of the Common Classes of Compounds Alcohols
43 Mass Spectra of the Common Classes of Compounds Alcohols (Phenols)
44 Mass Spectra of the Common Classes of Compounds Ethers (aliphatic)
45 Mass Spectra of the Common Classes of Compounds Ethers
46 Mass Spectra of the Common Classes of Compounds Ethers
47 Mass Spectra of the Common Classes of Compounds Aromatic Ethers (phenolethers)
48 Mass Spectra of the Common Classes of Compounds Ketones
49 Mass Spectra of the Common Classes of Compounds Ketones (aliphatic)
50 Mass Spectra of the Common Classes of Compounds Ketones (cyclic)
51 Mass Spectra of the Common Classes of Compounds Ketones (aromatic)
52 Mass Spectra of the Common Classes of Compounds Aldehydes (aliphatic) aromatic
53 Mass Spectra of the Common Classes of Compounds Carboxylic Acids (aliphatic)
54 Mass Spectra of the Common Classes of Compounds Carboxylic Acids (aromatic)
55 Mass Spectra of the Common Classes of Compounds Carboxylic Acid Esters (aliphatic)
56 Mass Spectra of the Common Classes of Compounds Carboxylic Acid Esters (benzyl, phenyl esters, aromatic acids)
57 Mass Spectra of the Common Classes of Compounds Carboxylic Acid Esters (lactones)
58 Mass Spectra of the Common Classes of Compounds Amines (aliphatic)
59 Mass Spectra of the Common Classes of Compounds Amines (cyclic and aromatic)
60 Mass Spectra of the Common Classes of Compounds Amides
61 Mass Spectra of the Common Classes of Compounds Nitriles
62 Mass Spectra of the Common Classes of Compounds Nitro compounds
63 Mass Spectra of the Common Classes of Compounds Sulfur compounds (thiols, sulfides)
64 Mass Spectra of the Common Classes of Compounds Sulfur compounds (thiols, sulfides)
65 Mass Spectra of the Common Classes of Compounds Halogen compounds
66 Mass Spectra of the Common Classes of Compounds Halogen compounds
67 Mass Spectra of the Common Classes of Compounds Aliphatic Chlorides
68 Mass Spectra of the Common Classes of Compounds Heteroaromatic compounds
69 References Silverstein, Webster, Kielme, Spectrometric Identification of Organic Compounds Wiley, 2005 Bruice, Organic Chemistry, Prentice Hall, 2005
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