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Related Concept Videos

IR and UV–Vis Spectroscopy of Carboxylic Acids01:28

IR and UV–Vis Spectroscopy of Carboxylic Acids

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, 1710 cm−1. The C=O bond of the...
IR Frequency Region: Alkene and Carbonyl Stretching01:29

IR Frequency Region: Alkene and Carbonyl Stretching

Double bonds in alkenes and carbonyl compounds exhibit stretching frequencies in the diagnostic region of the IR spectrum. In addition, alkenes exhibit vinylic C–H stretching and C–H out-of-plane bending absorptions that are useful for identifying substitution patterns.
Stretching frequencies are affected by several factors, such as resonance, inductive effects, ring strain, dipole moment, and hydrogen bonding. Consequently, the stretching frequency of the carbonyl double bond varies in...
Spectroscopy of Carboxylic Acid Derivatives01:26

Spectroscopy of Carboxylic Acid Derivatives

Infrared spectroscopy is primarily used to determine the types of bonds and functional groups. In carboxylic acid derivatives, a typical carbonyl bond absorption is observed around 1650–1850 cm−1. For esters, the absorption is recorded at around 1740 cm−1, while acid halides show the absorption at about 1800 cm−1. Another acid derivative, the acid anhydrides, exhibit two carbonyl absorption around 1760 cm−1 and 1820 cm−1, arising from the symmetrical and unsymmetrical carbonyl vibration.
In the...
IR Frequency Region: X–H Stretching01:24

IR Frequency Region: X–H Stretching

In IR spectroscopy, signals produced by the X−H bonds (such as C−H, O−H, or N−H) can be observed in the frequency range of  2700–4000 cm–1. The C−H stretching vibration forms sharp bands in the region 2850–3000 cm–1. The presence of the O−H stretching vibration leads to the forming of an absorption band in the frequency range 3650–3200 cm−1. At the same time, N−H stretching can be confirmed by absorption bands in the 3500–3100 cm−1 range. Even though both O−H and N−H bonds vibrate at a similar...
IR Spectrum Peak Splitting: Symmetric vs Asymmetric Vibrations01:08

IR Spectrum Peak Splitting: Symmetric vs Asymmetric Vibrations

Identical bonds within a polyatomic group can stretch symmetrically (in-phase) or asymmetrically (out-of-phase). Similar to hydrogen bonding, these vibrations also influence the shape of the IR peak. Generally, asymmetric stretching frequencies are higher than symmetric stretching frequencies. For example, primary amines exhibit two distinct IR peaks between 3300–3500 cm−1 corresponding to the symmetric and asymmetric N-H stretching, while secondary amines exhibit a single stretching vibration...
IR Frequency Region: Alkyne and Nitrile Stretching01:22

IR Frequency Region: Alkyne and Nitrile Stretching

Both alkyne (C≡C) and nitrile (C≡N) functional groups contain triple bonds and show stretching absorptions around the wavenumber range of 2100 to 2300 cm−1 in the diagnostic region of the IR spectra.
Comparing the stretching vibrational frequency of  C≡C triple bonds with that of double and single bonds, it is evident that C≡C triple bonds exhibit a higher stretching frequency than C=C double and C–C single bonds. Similarly, the C≡N triple bond exhibits higher stretching absorption than the C=N...

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Free carboxylate stretching modes.

Jos Oomens, Jeffrey D Steill

    The Journal of Physical Chemistry. A
    |March 28, 2008
    PubMed
    Summary
    This summary is machine-generated.

    Infrared spectroscopy reveals carboxylate stretching in the gas phase, free from solvent effects. Environmental influences significantly alter these vibrational modes in benzoate anions.

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    Area of Science:

    • Physical Chemistry
    • Spectroscopy
    • Molecular Physics

    Background:

    • Carboxylate groups are ubiquitous in organic chemistry and biochemistry.
    • Understanding their vibrational properties is crucial for molecular characterization.
    • Previous studies were limited by environmental influences like solvents and counterions.

    Discussion:

    • First infrared (IR) spectroscopic observation of carboxylate stretching modes in free space (gas phase).
    • Comparison of gas-phase spectra with condensed-phase spectra of benzoate anions.
    • Analysis of the environmental impact on symmetric and antisymmetric carboxylate stretching frequencies.

    Key Insights:

    • The gas-phase spectra provide a benchmark for intrinsic carboxylate vibrational behavior.
    • Significant shifts in symmetric and antisymmetric carboxylate stretches are observed between gas and condensed phases.
    • Environmental factors, including solvation and counterion interactions, profoundly influence carboxylate vibrational modes.

    Outlook:

    • Enables more accurate interpretation of carboxylate vibrations in complex systems.
    • Opens avenues for studying isolated carboxylate ions and their intrinsic properties.
    • Provides foundational data for computational chemistry models of carboxylate systems.