Chapter 13 Spectroscopy

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1 hapter 13 Spectroscopy Infrared spectroscopy Ultraviolet-Visible spectroscopy Nuclear magnetic resonance spectroscopy Mass Spectrometry

2 13.1 Principles of Molecular Spectroscopy: Electromagnetic Radiation

3 Electromagnetic Radiation is propagated at the speed of light has properties of particles and waves the energy of a photon is proportional to its frequency

4 Figure 13.1: The Electromagnetic Spectrum Shorter Wavelength (λ)( Longer Wavelength (λ)( 400 nm 750 nm Visible Light igher Frequency (ν)( Lower Frequency (ν)( igher Energy (E)( Lower Energy (E)(

5 Figure 13.1: The Electromagnetic Spectrum Shorter Wavelength (λ)( Longer Wavelength (λ)( Ultraviolet Infrared igher Frequency (ν)( Lower Frequency (ν)( igher Energy (E)( Lower Energy (E)(

6 Figure 13.1: The Electromagnetic Spectrum Energy osmic rays γ Rays X-rays Ultraviolet light Visible light Infrared radiation Microwaves Radio waves

7 13.2 Principles of Molecular Spectroscopy: Quantized Energy States

8 E E = hνh Electromagnetic radiation is absorbed when the energy of photon corresponds to difference in energy between two states.

9 What Kind of States? electronic vibrational rotational nuclear spin UV-Vis Vis infrared microwave radiofrequency

10 13.3 Introduction to 1 NMR Spectroscopy

11 The nuclei that are most useful to organic chemists are: 1 and 13 both have spin = ±1/2 1 is 99% at natural abundance 13 is 1.1% at natural abundance

12 Nuclear Spin + + A spinning charge, such as the nucleus of 1 or 13, generates a magnetic field.. The magnetic field generated by a nucleus of spin +1/2 is opposite in direction from that generated by a nucleus of spin 1/2.

13 The distribution of nuclear spins is random in the absence of an external magnetic field

14 An external magnetic field causes nuclear magnetic moments to align parallel and antiparallel to applied field

15 There is a slight excess of nuclear magnetic moments aligned parallel to the applied field

16 Energy Differences Between Nuclear Spin States + E E ' + increasing field strength no difference in absence of magnetic field proportional to strength of external magnetic field

17 Some important relationships in NMR The frequency of absorbed electromagnetic radiation is proportional to the energy difference between two nuclear spin states which is proportional to the applied magnetic field

18 Some important relationships in NMR The frequency of absorbed electromagnetic radiation is proportional to the energy difference between two nuclear spin states which is proportional to the applied magnetic field Units z kj/mol (kcal/mol) tesla (T)

19 Some important relationships in NMR The frequency of absorbed electromagnetic radiation is different for different elements, and for different isotopes of the same element. For a field strength of 4.7 T: 1 absorbs radiation having a frequency of 200 Mz (200 x 10 6 s -1 ) 13 absorbs radiation having a frequency of 50.4 Mz (50.4 x 10 6 s -1 )

20 Some important relationships in NMR The frequency of absorbed electromagnetic radiation for a particular nucleus (such as 1 ) depends on its molecular environment. This is why NMR is such a useful tool for structure determination.

21 13.4 Nuclear Shielding and 1 hemical Shifts What do we mean by "shielding?" What do we mean by "chemical shift?"

22 Shielding An external magnetic field affects the motion of the electrons in a molecule, inducing a magnetic field within the molecule. 0

23 Shielding An external magnetic field affects the motion of the electrons in a molecule, inducing a magnetic field within the molecule. The direction of the induced magnetic field is opposite to that of the applied field. 0

24 Shielding The induced field shields the nuclei (in this case, and ) from the applied field. A stronger external field is needed in order for energy difference between spin states to match energy of rf radiation. 0

25 hemical Shift hemical shift is a measure of the degree to which a nucleus in a molecule is shielded. Protons in different environments are shielded to greater or lesser degrees; they have different chemical shifts. 0

26 Downfield Decreased shielding Upfield Increased shielding ( 3 ) 4 Si (TMS) hemical shift (δ,(, ppm) measured relative to TMS

27 δ 7.28 ppm l l l hemical shift (δ,(, ppm)

28 13.5 Effects of Molecular Structure on 1 hemical Shifts protons in different environments experience different degrees of shielding and have different chemical shifts

29 Electronegative substituents decrease the shielding of methyl groups 3 F 3 O 3 3 N( 3 ) Si( 3 ) 3 δ 4.3 ppm δ 3.2 ppm δ 2.2 ppm δ 0.9 ppm δ 0.0 ppm

30 Electronegative substituents decrease the shielding of methyl groups 3 F 3 O 3 3 N( 3 ) Si( 3 ) 3 δ 4.3 ppm least shielded δ 3.2 ppm δ 2.2 ppm δ 0.9 ppm δ 0.0 ppm most shielded

31 Effect is cumulative l l 3 2 l 2 3 l δ 7.3 ppm δ 5.3 ppm δ 3.1 ppm

32 Protons attached to sp 2 hybridized carbon are less shielded than those attached to sp 3 hybridized carbon 3 3 δ 7.3 ppm δ 5.3 ppm δ 0.9 ppm

33 Table 13.1 (p 496) Type of proton hemical shift (δ),( ppm Type of proton hemical shift (δ),( ppm R Ar O

34 Table 13.1 (p 496) Type of proton hemical shift (δ),( ppm Type of proton hemical shift (δ),( ppm Ar l O 9-10 Br NR O

35 Table 13.1 (p 496) Type of proton hemical shift (δ),( ppm NR 1-3 OR O OAr O

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