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m/z = 30
-Peaks due to ring formation reaction
producing a series of even-electron
fragments at m/z 58, 72, 86, 100 and
114.
NH2 CH2N+H2
RCH2 R +
(CH2)n (CH2)n
- The spectrum of 2-
butanamine shows a base
peak at m/z 44 (loss of the
ethyl group) and less intense
peak at m/z 58 corresponding
to loss of the methyl group.
2-Butanamine
3,3-Dimethyl-2-butanamine
- Aromatic amines, exhibit a molecular
ion peak that we have observed in other
aromatic compounds. Similar losses of
HCN from the molecular ion and from
(M-H) account for the lines at m/z 66
and 65 in the spectrum of aniline N-
Methylaniline produces a spectrum
which is almost indistinguishable from
that of 2-methylaniline.
Aniline
Amides
- The mass spectra of amides usually show an
observable molecular ion peak. The fragmentation
patterns of amides are quite similar to those of the
corresponding esters and acids.
- The presence of a strong fragment ion peak at m/e
= 44 is usually indicative of a primary amide. This
peak arises from -cleavage of the following sort:
-McLafferty rearrangements become
possible, for primary amides, the
McLafferty rearrangement gives rise to a
fragment ion peak at m/e = 59
-In the spectrum of butananamide
we see a weak molecular ion at
m/z 87.
-We also see lines at m/z 72
(cleavage between the - and -
carbons), m/z 59 (the McLafferty
rearrangement peak), and m/z 44
(loss of the alkyl group).
CH3CH2CH2CONH2
Butnamide
- The spectrum of benzamide
exhibits the molecular ion at m/z
121.
- Other peaks include m/z 105 (loss
of NH2), m/z 77 (loss of CO from
m/z 105) and m/z 51 (loss of
C2H2 from m/z 77).
Nitriles
-Aliphatic nitriles usually undergo
fragmentation so readily that the
molecular ion peak is too weak to be
observed. However, most nitriles form a
peak due to the loss of one hydrogen
atom, forming an ion of the type R
CH=C=N+.
-When the alkyl group attached to the
nitrile functional group is a propyl group
or some longer hydrocarbon group,
the most intense peak in the mass
spectrum results from a McLafferty
rearrangement:
-The strongest peak in the mass spectrum
of an aromatic nitrile is the molecular
ion peak. Loss of cyanide occurs, giving,
in the case of benzonitrile, the C6H5+
ion at m/e = 77. more important
fragmentation involves loss of the
elements of hydrogen cyanide.
- In benzonitrile, this gives rise to a peak
at m/e = 76.
Nitro Compounds
-The molecular ion peak for an aliphatic
nitro compound is seldom observed.
-The mass spectra of nitro compounds may
show a moderate peak at m/e = 30,
corresponding to the NO+ ion, and a
weaker peak at m/e = 46, corresponding to
the NO2+ ion. These peaks may be
observed in the mass. The intense peak at
m/e = 43 is due to the C3H7+ ion.
- Aromatic nitro compounds show an intense
molecular ion peak. The characteristic NO+ (m/e =
30) and NO2+ (m/e = 46) peaks may be found in the
mass spectrum.