In organosulfur chemistry, a sulfonyl group is either a functional group found primarily in sulfones, or a substituent obtained from a sulfonic acid by the removal of the hydroxyl group, similarly to acyl groups.
Group
Sulfonyl groups can be written as having the general formula R−S(=O)2−R′, where there are two double bonds between the sulfur and oxygen.
Sulfonyl groups can be reduced to the sulfide with diisobutylaluminium hydride (DIBALH). Lithium aluminium hydride (LiAlH4) reduces some but not all sulfones to sulfides.
In inorganic chemistry, when the group −S(=O)2− is not connected to any carbon atoms, it is referred to as sulfuryl.
Examples of sulfonyl group substituents
The names of sulfonyl groups typically end in -syl, such as:
Group name Full name Pseudoelement symbol Example Tosyl p-toluenesulfonyl Ts Tosyl chloride (p-toluenesulfonyl chloride)
CH3C6H4SO2ClBrosyl p-bromobenzenesulfonyl Bs Nosyl o- or p-nitrobenzenesulfonyl Ns Mesyl methanesulfonyl Ms Mesyl chloride (methanesulfonyl chloride)
CH3SO2ClTriflyl trifluoromethanesulfonyl Tf Tresyl 2,2,2-trifluoroethyl-1-sulfonyl Dansyl 5-(dimethylamino)naphthalene-1-sulfonyl Ds Dansyl chloride
See also
References
- ^ Smith, Michael B.; March, Jerry (2007). March's Advanced Organic Chemistry (6th ed.). John Wiley & Sons. ISBN 978-0-471-72091-1.
- Clayden, Jonathan; Greeves, Nick; Warren, Stuart; Wothers, Peter (2001). Organic Chemistry (1st ed.). Oxford University Press. pp. 1249–1251. ISBN 978-0-19-850346-0.
- Greenwood, Norman N.; Earnshaw, Alan (1997). Chemistry of the Elements (2nd ed.). Butterworth-Heinemann. pp. 694–695. ISBN 978-0-08-037941-8.
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| Only one element, not being carbon, hydrogen, or oxygen (one element, not C, H or O) |
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