Amines

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Amines

• By
• David Eastwood
• Morgan Gentes

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What is an Amine?

• Amines are found everywhere. They appear mainly
  in decaying animal and plant matter. Amines are
  what give off a pungent odour, mainly being the
  one we recognize as decaying flesh. Ironically,
  amines are also are huge part of the compositions
  of perfumes and colognes. Animals are attracted
  to the scent of decaying flesh. Apparently so are
  humans.

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Structure

• Amines are a derivative of ammonia where one or
  more hydrogen atoms are replaced by an
  substituent.

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cyclobutyl amine or cyclobutanamine
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Nomenclature

• When naming Amines, use the prefix amino and
  the suffix -amine.
• Lower amines
• are named with the suffix -amine.
• H H
• \
• N C H
• /
• H H
• Methylamine

• Since we know that the more oxidized (bonds to
  oxygen) group is the principal group, in some
  cases in may not be the suffix amine used but the
  prefix amino. In other situations,
• H2N OH
• \ /
• C-C-C-C
• 3-amino-1-propanol

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• RNH2 R2NH
  R3N
• Primary Secondary
  Tertiary
• Amine Amine
  Amine

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Ammonia VS. Amine

• The chemistry of amines and ammonia are
  similar. The most obvious feature is their
  basicity (being able to accept a proton) which
  comes from the unshared pair of electrons in the
  nitrogen atom.
• Comparing acceptance of a proton in an Amine
  and an ammonia is shown
• H
  H
• R\
  R\
• R- N H? R N H R- N H? R
  N H
• R/
  R/
• R
  R

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• Drawing amines is just as simple as naming them.
  N represents a locator, just like numbers.
• Ex. N-ethyl-3-methyl-1-pentanamine
• CH3 N-CH2-CH3
• l /
• CH3-CH2-CH-CH2-CH

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• Draw 1-amino-2-methyl-5-octene-7-ol
• OH
  NH2
• \
  /
• CH2-CH-CC-CH-CH2-CH-CH2
• 
  
• 
  CH3

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Methylamine
http//upload.wikimedia.org/wikipedia/commons/arch
ive/7/7f/20100103095327!Methylamine-2D.png
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ethyl amine or ethanamine
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3-amino-2,6-dimethyl-4-propyloctane

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Prepared Amines

• Amines can be prepared by a substitution process
  called Alkylation, where an alkyl group becomes
  bonded to a Nitrogen.
• http//www.chem.ucalgary.ca/courses/351/Carey5th/C
  h22/ch22-3-1.html

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Reactions
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References

• www.chem.ucalgary.ca/courses/350/Carey/.../amines/
  amines-1.html
• McMurry, John E. (1992), Organic Chemistry (3rd
  ed.), Belmont Wadsworth, ISBN 0-534-16218-5
• Lide, D. R., ed. (2005), CRC Handbook of
  Chemistry and Physics (86th ed.), Boca Raton
  (FL) CRC Press, ISBN 0-8493-0486-5
• Karsten Eller, Erhard Henkes, Roland
  Rossbacher, Hartmut Höke "Amines, Aliphatic" in
  Ullmann's Encyclopedia of Industrial Chemistry,
  Wiley-VCH, Weinheim, 2005. doi10.1002/14356007.a0
  2_001
• March, Jerry (1992), Advanced Organic
  Chemistry Reactions, Mechanisms, and Structure
  (4th ed.), New York Wiley, ISBN 0-471-60180-2