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Related Concept Videos

IR Spectrum Peak Broadening: Hydrogen Bonding01:23

IR Spectrum Peak Broadening: Hydrogen Bonding

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The vibrational frequency of a bond is directly proportional to its bond strength. As a result, stronger bonds vibrate at higher frequencies, while weaker bonds vibrate at lower frequencies. The stretching vibration of the strong O–H bond in alcohols and phenols (very dilute solution or gas phase) appears as a sharp peak at 3600–3650 cm−1.
However, the extent of hydrogen bonding influences the observed stretching frequency and band broadening. Intermolecular or intramolecular...
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Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

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Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
22.9K
IR and UV–Vis Spectroscopy of Carboxylic Acids01:28

IR and UV–Vis Spectroscopy of Carboxylic Acids

6.2K
In IR spectroscopy of carboxylic acids, the C=O bond shows a characteristic band between 1710 and 1760 cm⁻¹, and the O–H bond exhibits a broad band between 2500 and 3300 cm⁻¹.
However, the stretching absorptions for the C=O bond vary depending on the structure of carboxylic acids. The C=O bond of the free carboxylic acids shows a higher stretching frequency, 1760 cm−1, while H-bonded carboxylic acids (dimers) exhibit stretching absorptions at a lower frequency,...
6.2K
IR Spectroscopy: Molecular Vibration Overview01:24

IR Spectroscopy: Molecular Vibration Overview

6.2K
When Infrared (IR) radiation passes through a covalently bonded molecule, the bonds transition from lower to higher vibrational levels. The fundamental vibrational motions that result in infrared absorption can be classified as stretching or bending vibrations.
Stretching vibrations are vibrational motions that occur along the bond line, changing the bond length or distance between two bonded atoms. They are further distinguished as symmetric or asymmetric. In symmetric stretching, the...
6.2K
Mass Spectrometry: Alcohol Fragmentation01:03

Mass Spectrometry: Alcohol Fragmentation

4.8K
Alcohols (R-OH) ionize to lose one non-bonded electron from the oxygen atom, forming molecular ions. Due to their tendency to fragment rapidly, the intensity of the molecular ion peak in the mass spectrum is weak or sometimes absent. The fragmentation patterns for alcohols occur in two ways, i.e. ⍺-cleavage and dehydration. During ⍺-cleavage, the bond at the ⍺-position adjacent to the hydroxyl group cleaves to give a resonance-stabilized cation and a radical. However, intramolecular...
4.8K
Acidity of 1-Alkynes02:42

Acidity of 1-Alkynes

11.6K

The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
11.6K

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Unveiling Superacidity in Alcohol-BF3 Complexes Using a Vibrational Probe.

Keerthy P Sudhakaran1, Cole Sanchez2, Jonathan Tong2

  • 1Department of Chemistry, Seaver Science Center, University of Southern California, Los Angeles, California 90089, United States.

The Journal of Physical Chemistry Letters
|April 3, 2026
PubMed
Summary
This summary is machine-generated.

Boron trifluoride (BF3) forms superacidic complexes with alcohols. Using deuterated acetonitrile as a probe, researchers quantified hydrogen bonding and acidity in these systems, revealing potential for new reagents.

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Area of Science:

  • Chemistry
  • Physical Chemistry
  • Supramolecular Chemistry

Background:

  • Boron trifluoride (BF3) is a potent Lewis acid forming complexes with Lewis bases like water and alcohols.
  • These BF3-alcohol complexes exhibit strong Brønsted acidity, some reaching the superacidity range.
  • While their catalytic applications are known, their hydrogen bonding properties remain understudied.

Purpose of the Study:

  • To systematically investigate hydrogen bonding in BF3-alcohol complexes.
  • To quantify the acidity of these complexes using a vibrational probe.
  • To explore the potential of these complexes as next-generation reagents.

Main Methods:

  • Utilized deuterated acetonitrile as a vibrational probe to assess hydrogen bonding.
  • Measured the blue shift in the CN vibrational frequency of acetonitrile.
  • Employed computational methods to confirm acidity and analyze electronic structure changes.

Main Results:

  • Observed a linear blue shift in CN frequency correlating with alcohol acidity.
  • BF3 complexation significantly enhanced the blue shift, indicating superacidic properties.
  • The hexafluoroisopropanol (HFIP)-BF3 complex exhibited higher acidity than triflic acid.

Conclusions:

  • Nitrile frequency serves as a sensitive probe for hydrogen bonding and acidity, even in the superacidity range.
  • BF3-alcohol complexes represent a tunable class of superacidic systems.
  • This research provides a method for quantifying superacidic environments and designing novel reagents.