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Regioselectivity and Stereochemistry of Hydroboration

Regioselectivity and Stereochemistry of Hydroboration

A significant aspect of hydroboration–oxidation is the regio- and stereochemical outcome of the reaction.
Hydroboration proceeds in a concerted fashion with the attack of borane on the π bond, giving a cyclic four-centered transition state. The –BH2 group is bonded to the less substituted carbon and –H to the more substituted carbon. The concerted nature requires the simultaneous addition of –H and –BH2 across the same face of the alkene giving syn...

Regioselectivity and Stereochemistry of Acid-Catalyzed Hydration

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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.

Chair Conformation of Cyclohexane

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The chair conformation is the most stable form of cyclohexane due to the absence of angle and torsional strain. The absence of angle strain is a result of cyclohexane’s bond angle being very close to the ideal tetrahedral bond angle of 109.5° in its chair conformer. Similarly, the torsional strain is also absent owing to the perfectly staggered arrangement of bonds.
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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...

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Introduction
Analogous to alkenes, alkynes also undergo acid-catalyzed hydration. While the addition of water to an alkene gives an alcohol, hydration of alkynes produces different products such as aldehydes and ketones.

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Resolving a three-decade misassignment in hydroxylated C60 chemistry.

Yue Xu^1,2, Martina Stella^3,4, Stefan Knecht³

¹Biomedical Engineering, Cleveland Clinic Research, Cleveland, OH, USA.

Communications Chemistry

|April 22, 2026

Summary

This summary is machine-generated.

Researchers corrected the assumed structure of water-soluble fullerenols, revealing they contain carbonyl and hemiketal groups alongside hydroxyls, not just hydroxyls. This finding resolves long-standing inconsistencies in fullerene chemistry and nanocarbon properties.

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Preparation and Characterization of C60/Graphene Hybrid Nanostructures

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Published on: May 15, 2018

Area of Science:

Nanocarbon Chemistry
Materials Science
Spectroscopy
Computational Chemistry

Background:

Water-soluble functionalized fullerenes (fullerenols) are widely applied in photonics, catalysis, and biomedicine.
For decades, their structure was assumed to be solely hydroxylated, despite spectral and reactivity discrepancies.

Purpose of the Study:

To resolve the long-standing discrepancy between assumed and observed properties of fullerenols.
To accurately determine the molecular structure of water-soluble functionalized fullerenes.

Main Methods:

Combined Fourier transform infrared (FTIR) and UV-Vis absorption spectroscopy.
Utilized X-ray photoelectron spectroscopy (XPS) and targeted chemical derivatization.
Employed computational quantum chemistry for structural modeling.

Main Results:

A polyoxy-fullerene structure with carbonyl and hemiketal groups, alongside hydroxyls, accurately matched experimental FTIR and UV-Vis spectra.
A purely hydroxylated model failed to reproduce key spectral features.
Oxime-formation experiments chemically confirmed the presence of carbonyl and hemiketal functionalities.

Conclusions:

The study corrects a pervasive misinterpretation of fullerene structures, revealing a more complex polyoxy-fullerene architecture.
This structural reassignment resolves inconsistencies in fullerene chemistry and reactivity.
Establishes a framework for rational tuning of functionalized nanocarbon properties.