Nitrogen and Sulfur Containing Groups (5/14)
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Amines
NH3, but one or more of the hydrogens are replaced by an alkyl group
Naming amines
ends in amine if that is the highest priority. If a higher priority is present, then it starts with amino to show that there is an amine group
Cyclic amines
always secondary or tertiary
Primary and secondary amines physical and chemical properties
can participate in hydrogen bonding gives a higher boiling point so primary tend to have higher boiling points than secondary and tertiary
Amines as bases
they are weak bases alkyl: regular aryl: have an aromatic substituent
Aniline
simplest aryl because it is a benzene ring with an NH2 group attached
Butylamine
more basic than aryl
Imine
the oxygen in a carbonyl carbon is replaced by an N-R3 group
Enamines
have an alkene and an amine -carbon carbon double bond is also attached to an amine
Tautomerism
enamine and imines can easily go back and fourth under acidic or basic conditions
Amides
carboxylic acid derivatives with N-R-H group weak bases
Thiol
R-S-H
Thioether
R-S-R2
Thioester
R-C=O-SR2
Thiols
contain an SH group polar but weak hydrogen bond dipole dipole are main interactions lower boiling points than alcohols, but are more acidic
Thioethers
no acidic hydrogens, so they act as bases, but are not very basic can be part of a ring system EX) biotin and methionine
How thioesters are produced
esterification Thiol + carboxylic acid –> thioester
Disulfide
two sulfurs bonded by covalent bonds R-S-S-R2