Related Experiment Video
Updated: Aug 6, 2026
06:44
From Molecules to Materials: Engineering New Ionic Liquid Crystals Through Halogen Bonding
Published on: March 24, 2018
Very Short Single-Acceptor Hydrogen Bonding in Liquid Chlorosulfonic Acid Enables Long Chain Formation
Miroslava Novoveska1, Thomas F Headen2, Anna Herlihy3
1Department of Chemistry, University College London, 20 Gordon Street, London, WC1H 0AJ, U.K.
The Journal of Physical Chemistry Letters
|July 22, 2026
Summary
Chlorosulfonic acid
Area of Science:
- Physical Chemistry
- Inorganic Chemistry
- Materials Science
Background:
- Chlorosulfonic acid is a potent superacid.
- It is extensively utilized as a sulfonating and chlorosulfonating agent.
Purpose of the Study:
- To elucidate the intra- and intermolecular structure of chlorosulfonic acid in its liquid phase.
- To investigate the interactions governing its behavior.
Main Methods:
- Employed total neutron and X-ray scattering techniques.
- Analyzed scattering data to determine structural parameters and interactions.
Main Results:
- Observed very short intermolecular hydrogen bonds (1.43 Å and 1.66 Å) between hydroxyl and sulfonyl oxygen groups.
- Identified formation of branched head-to-tail chains due to hydrogen bonding.
- Noted distortion of intramolecular structure with three near-equal S-O bond lengths.
Conclusions:
- Hydrogen bonding significantly influences the liquid-phase structure and behavior of chlorosulfonic acid.
- The observed structural characteristics correlate with its properties as a superacid, including low viscosity and high acidity.
Related Concept Videos
01:01Acid Halides to Carboxylic Acids: Hydrolysis
Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
As shown below, the mechanism involves a nucleophilic attack by water at the carbonyl carbon to form a tetrahedral intermediate. This is followed by the reformation of the carbon–oxygen π bond along with the departure of a halide ion. A final proton transfer step yields carboxylic acid...
02:41Formation of Halohydrin from Alkenes
An alkene, such as propene, reacts with bromine in the presence of water to yield a halohydrin. Halohydrins contain a halogen and a hydroxyl group attached to adjacent carbons. When the halogen is bromine, it is called a bromohydrin, while a chlorohydrin has chlorine as the halogen.
01:18Carboxylic Acids to Acid Chlorides
Carboxylic acids react with SOCl2 or PCl5 to form acid chlorides. Amongst the carboxylic acid derivatives, acid chlorides are the most reactive and synthetically important derivatives. They are useful reagents for Friedel–Crafts acylation of some aromatic compounds.
02:45Alkyl Halides
Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
02:34Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration
The rate of acid-catalyzed hydration of alkenes depends on the alkene's structure, as the presence of alkyl substituents at the double bond can significantly influence the rate.
02:26Preparation and Reactions of Sulfides
Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.