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    L3 NMR 1

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    Cheng Fu
    Nuclear magnetic resonance (NMR) spectroscopy provides information about carbon and hydrogen frameworks of molecules. 1H and 13C nuclei have nuclear spin and act like tiny magnets in an applied magnetic field. The absorption frequency is different for each unique 1H or 13C in a molecule, depending on chemical shielding. In NMR spectra, absorption positions are reported as chemical shifts (δ) in parts per million (ppm) downfield from tetramethylsilane (TMS). 13C NMR spectra show signals between 0-90 ppm for sp3 carbons and 100-210 ppm for sp2 carbons. 1H NMR spectra consider the number, position, relative area, and splitting pattern of absorption signals

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    L3 NMR 1

    Uploaded by

    Cheng Fu
    12 views13 pages
    Nuclear magnetic resonance (NMR) spectroscopy provides information about carbon and hydrogen frameworks of molecules. 1H and 13C nuclei have nuclear spin and act like tiny magnets in an applied magnetic field. The absorption frequency is different for each unique 1H or 13C in a molecule, depending on chemical shielding. In NMR spectra, absorption positions are reported as chemical shifts (δ) in parts per million (ppm) downfield from tetramethylsilane (TMS). 13C NMR spectra show signals between 0-90 ppm for sp3 carbons and 100-210 ppm for sp2 carbons. 1H NMR spectra consider the number, position, relative area, and splitting pattern of absorption signals

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    Nuclear magnetic resonance (NMR) spectroscopy provides information about carbon and hydrogen frameworks of molecules. 1H and 13C nuclei have nuclear spin and act like tiny magnets in an applied magnetic field. The absorption frequency is different for each unique 1H or 13C in a molecule, depending on chemical shielding. In NMR spectra, absorption positions are reported as chemical shifts (δ) in parts per million (ppm) downfield from tetramethylsilane (TMS). 13C NMR spectra show signals between 0-90 ppm for sp3 carbons and 100-210 ppm for sp2 carbons. 1H NMR spectra consider the number, position, relative area, and splitting pattern of absorption signals

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    12 views13 pages

    L3 NMR 1

    Uploaded by

    Cheng Fu
    Nuclear magnetic resonance (NMR) spectroscopy provides information about carbon and hydrogen frameworks of molecules. 1H and 13C nuclei have nuclear spin and act like tiny magnets in an applied magnetic field. The absorption frequency is different for each unique 1H or 13C in a molecule, depending on chemical shielding. In NMR spectra, absorption positions are reported as chemical shifts (δ) in parts per million (ppm) downfield from tetramethylsilane (TMS). 13C NMR spectra show signals between 0-90 ppm for sp3 carbons and 100-210 ppm for sp2 carbons. 1H NMR spectra consider the number, position, relative area, and splitting pattern of absorption signals

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    of 13

    5.

    Nuclear magnetic resonance (NMR)


    5.1 Introduction
    …… It provides information about the carbon and
    hydrogen framework of molecules.
    Certain nuclei have the property of nuclear spin and act
    like tiny bar magnets (eg 1H and 13C)..….
    applied
    field
    E

    no applied excitation from


    field(random lower to higher
    orientation) aligned energy spin state
    nuclei when E = h
    NMR MRI
    The absorption frequency is different for each unique
    kind of 1H or 13C in any molecule. ….. The applied
    magnetic field experienced by the nucleus, and hence
    the E for nuclear spin flip, will depend on the
    shielding of the nucleus.
    In an NMR spectrum positions of absorptions are
    known as chemical shifts and measured in  (delta)
    units (ppm) from the peak of a reference compound
    tetramethylsilane (TMS), (CH3)4Si. TMS is defined as 0
    .

     increasing frequency
    5.2 13C NMR
    All 13C NMR spectra considered in this course will be
    proton decoupled spectra. Proton decoupling
    means one does not observe splitting of signals
    which would otherwise be seen because of 13C−1H
    interaction.
    As stated above:
    each unique carbon will give rise to a
    different signal.
    Consider the proton 32.1→ 10.8
    decoupled 13C NMR 
    spectrum of butan-2-ol:
    1 2 3 4 69.3→ 22.9
    CH3CHCH2CH3
    OH 'four unique carbons'
    Chemical shift range for TMS
    13C is generally  0 –210.

    Cs bonded to electronegative substituents (O, N,


    halogen) will occur at higher  values…
    The electronegative atom pulls electrons
    towards itself and away from the attached
    carbon, whose nucleus is thus deshielded.
    [C2 is the signal at  69.3 in butan-2-ol.]
    In 13C NMR spectra sp3 carbons show signals between 
    0 – 90, whereas those for sp2 carbons are between 
    100 – 210.
    …..in 13C NMR the intensity of a signal is not an
    indication of number of Cs giving rise to a signal.

    5.2.1 Problems
    1. How many signals would be expected in the proton
    decoupled 13C NMR spectra of :

    O 2 O 4
    CH3CCH3 CH3CCH2CH3

    O
    CH3COCH3 OCH2CH3
    5.2.1 Problems
    1. How many signals would be expected in the proton
    decoupled 13C NMR spectra of :

    O 2 O 4
    CH3CCH3 CH3CCH2CH3
    6
    O 
    3  ◼ OCH2CH3
    CH3COCH3
    
    2. What structural information can you work out for a
    compound which has the proton decoupled 13C
    NMR spectrum:

    Three unique
    environments for C.

    Two environs sp3 carbons.


    One environ sp2 carbon.
    Given molecular formula is C3H6O2 could be:
    CH3CH2CO2H (1) or HCO2CH2CH3 (2) or
    CH3CO2CH3 (3). [ Actually 3 ].
    Practice question – 13C NMR

    Which structure is consistent with the 13C NMR spectrum?


    OH

    O
    B

    O
    C

    A = 3 x sp3, B = 2 x sp3 + 1 x sp2, C = 3 x sp2


    5.3 1H NMR
    In all 1H NMR spectra only hydrogens give rise
    to absorption signals.
    To interpret 1H NMR spectra have to consider:
    1. Number of absorption signals.

    2. Position of absorption signals.

    3. Relative areas under absorption


    signals.
    4. Splitting pattern for absorption
    signals.
    5.3.1 The number of absorption signals
    Hs in identical molecular environments give
    only one absorption signal.
    O
    Examples: CH3CCH3 ClCH2CH2Cl
    Hs in ‘X’ different molecular environments give
    ‘X’ absorption signals.
    No. of No. of
    signals signals
    CH3CH2Cl 2 CH3CH2OCH2CH3 2
    CH3CHCl2 2 3
    sometimes

    CH3CH2OH 1
    3 usually
    5.3.2 Position of the absorption signal
    Chemical shift range for 1H generally  0 – 15. Most
    signals observed in the  0 – 10 range.
    For hydrogen bonded to sp3
    carbon, considering the signal for: C E
    H
    as E increases in electronegativity (en) signal
    is observed at a higher  value.

    C Si C C C N C O
    (or halogen)
    H H H H
    en Si 1.9 C 2.5 N 3.0 O 3.5
     value (H) 0 1 ~3 ~3.5
    Note: Substituents containing double bonds
    deshield.
    For hydrogen bonded to sp2 carbon

    signals are at higher  values.

    TABLE 2
    1H
    NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY
    (1H NMR)
    Approximate Chemical Shifts () of Hydrogens in
    Organic Compounds

    - supplied in test and examination if


    required!

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