Spectroscopic methods in organic chemistry

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9780077118129: Spectroscopic methods in organic chemistry

Spectroscopic Method in Organic Chemistry is a well established introductory guide to the interpretation of ultraviolet, infrared, nuclear magnetic resonance and mass spectra of organic compounds. It can be used as a textbook for a first course in the application of these techniques to structure determination, as well as a handbook for synthetic organic chemists. Updates to the new edition are as follows: Structure: The same structure will be retained in this new edition. There will be five chapters – UV, IR, NMR and MS, followed by examples and problems. New edition content: The first four chapters have been completely rewritten to reflect changes that have taken place since the current edition published. Key changes include: • Coverage of UV and IR Spectra is more concise. • Coverage of NMR has been expanded. • Coverage of MS has been made more relevant to the everyday application of this technique. • IR Chapter has been restructured so that the spectra are displayed where they are being discussed, rather than at the end of the chapter. • Examples. All 60 MHz spectra have been replaced with new examples at 400 MHz or more.

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Contenuti:

Preface

Chapter 1: Ultraviolet and visible spectra

1.1 Introduction
1.2 Chromophores
1.3 The absorption laws
1.4 Measurement of the spectrum
1.5 Vibrational fine structure
1.6 Choice of solvent
1.7 Selection rules and intensity
1.8 Solvent effects
1.9 Searching for a chromophore
1.10 Definitions
1.11 Conjugated dienes
1.12 Polyenes
1.13 Polyeneynes and poly-ynes
1.14 Ketones and aldehydes; ¿¿¿* transitions
1.15 Ketones and aldehydes; n¿¿* transitions
1.16 ¿,¿-Unsaturated acids, esters, nitriles and amides
1.17 The benzene ring
1.18 Substituted benzene rings
1.19 Polycyclic aromatic hydrocarbons
1.20 Heteroaromatic compounds
1.21 Quinones
1.22 Corroles, chlorins and porphyrins
1.23 Non-conjugated interacting chromophores
1.24 The effect of steric hindrance to coplanarity
1.25 Internet
1.26 Bibliography

Chapter 2: Infrared spectra

2.1 Introduction
2.2 Preparation of samples and examination in an infrared spectrometer
2.3 Examination in a Raman spectrometer
2.4 Selection rules
2.5 The infrared spectrum
2.6 The use of the tables of characteristic group frequencies
2.7 Absorption frequencies of single bonds to hydrogen 3600-2000 cm–1
2.8 Absorption frequencies of triple and cumulated double bonds2300-1930 cm–1
2.9 Absorption frequencies of the double-bond region 1900-1500 cm–1
2.10 Groups absorbing in the fingerprint region <1500 cm–1
2.11 Internet
2.12 Bibliography
2.13 Correlation charts
2.14 Tables of data

Chapter 3: Nuclear magnetic resonance spectra

3.1 Nuclear spin and resonance
3.2 The measurement of spectra
3.3 The chemical shift
3.4 Factors affecting the chemical shift
3.4.1 Intramolecular factors affecting the chemical shift
3.4.2 Intermolecular factors affecting the chemical shift
3.5 Spin-spin coupling to 13C
3.5.1 13C-2H Coupling
3.5.2 13C-1H Coupling
3.5.3 13C-13C Coupling
3.6 1H-1H Vicinal coupling (3JHH)
3.7 1H-1H Geminal coupling (2JHH)
3.8 1H-1H Long-range coupling (4JHH and 5JHH)
3.9 Deviations from first-order coupling
3.10 The magnitude of 1H-1H coupling constants
3.10.1 Vicinal coupling 3JHH
3.10.2 Geminal coupling (2JHH)
3.10.3 Long-range coupling (4JHH and 5JHH)
3.11 Line broadening and environmental exchange
3.11.1 Efficient relaxation
3.11.2 Environmental exchange
3.12 Improving the NMR spectrum
3.12.1 The effect of changing the magnetic field
3.12.2 Shift reagents
3.12.3 Solvent effects
3.13 Spin decoupling
3.13.1 Simple spin decoupling
3.13.2 Difference decoupling
3.14 The nuclear Overhauser effect
3.14.1 Origins
3.14.2 NOE Difference spectra
3.15 Assignment of CH3, CH2, CH and quaternary carbons in 13C NMR
3.16 Identifying spin systems—1D-TOCSY
3.17 The separation of chemical shift and coupling onto different axes
3.18 Two-dimensional NMR
3.19 COSY spectra
3.20 NOESY spectra
3.21 2D-TOCSY spectra
3.22 1H-13C COSY spectra
3.22.1 Heteronuclear Multiple Quantum Coherence (HMQC) spectra
3.22.2 Heteronuclear Multiple Bond Connectivity (HMBC) spectra
3.23 Measuring 13C-1H coupling constants (HSQC-HECADE spectra)
3.24 Identifying 13C-13C connections (INADEQUATE spectra)
3.25 Three- and four-dimensional NMR
3.26 Hints for spectroscopic interpretation and structure determination
3.26.1 Carbon spectra
3.26.2 Proton spectra
3.26.3 Hetero-correlations
3.27 Internet
3.28 Bibliography
3.29 Tables of data

Chapter 4: Mass spectra

4.1 Introduction
4.2 Ion production from readily volatile molecules
4.2.1 Electron impact (EI)
4.2.2 Chemical Ionisation (CI)
4.3 Ion production from poorly volatile molecules
4.3.1 Fast ion bombardment (FIB or LSIMS)
4.3.2 Laser desorption (LD) and matrix-assisted laserdesorption (MALDI)
4.3.3 Electrospray ionisation (ESI)
4.4 Ion analysis
4.4.1 Magnetic analysers
4.4.2 Combined magnetic and electrostatic analysers—high-resolutionmass spectra (HRMS)
4.4.3 Ion cyclotron resonance (ICR) analysers
4.4.4 Time-of–flight (TOF) analysers
4.4.5 Quadrupole analysers
4.4.6 Ion-trap analysers
4.5 Structural information from mass spectra
4.5.1 Isotopic abundances
4.5.2 EI spectra
4.5.3 CI spectra
4.5.4 FIB (LSMIS) spectra
4.5.5 MALDI spectra
4.5.6 ESI spectra
4.5.7 ESI-FT-ICR and ESI-FT-Orbitrap spectra
4.6 Separation coupled to mass spectrometry
4.6.1 GC/MS and LC/MS
4.6.2 MS/MS
4.7 MS data systems
4.8 Specific ion monitoring and quantitative MS (SIM and MIM)
4.9 Interpreting the spectrum of an unknown
4.10 Internet
4.11 Bibliography
4.12 Tables of data

Chapter 5: Practice in structure determination

5.1 General approach
5.2 Simple worked examples using 13C NMR alone
5.3 Simple worked examples using 1H NMR alone
5.4 Simple worked examples using the combined application of all fourspectroscopic methods
5.5 Simple problems using 13C NMR or joint application of IR and 13C NMR
5.6 Simple problems using 1H NMR
5.7 Problems using a combination of spectroscopic methods
5.8 Answers to problems 1-33
Index

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