||Chapter 15: Alcohols, Diols
Thiols are the sulfur analogues of alcohols.
Functional group suffix = -thiol (review)
Functional group prefix = mercapto-
- Hydrogen bonding is much
weaker than that in alcohols.
- Lower boiling points than similar
- Generally similar to alcohols,
but bonds to S are longer and weaker than those to O.
- The thiol functional group consists
of an S atom bonded to a C atom and a H atom via s bonds.
- The S-H bonds is less
polar than that in alcohols since S is less electronegativity than O.
- Thiols are much more acidic than
similar alcohols, e.g. RSH (pKa = 10) versus ROH (pKa
= 16 to 19)
- Thiols are also much more nucleophilic
than similar alcohols, infact RSH is about as nucleophilic as RO-
- Thiols are readily oxidised but
to S-O systems rather than C=S systems.
- Thiols are commonly oxidised
to disulfides, R-S-S-R, a biologically important reaction.
||© Dr. Ian Hunt, Department of Chemistry, University