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Related Concept Videos

NMR Spectroscopy of Benzene Derivatives01:34

NMR Spectroscopy of Benzene Derivatives

11.0K
Simple unsubstituted benzene has six aromatic protons, all chemically equivalent. Therefore, benzene exhibits only a singlet peak at δ 7.3 ppm in the 1H NMR spectrum. The observed shift is far downfield because the aromatic ring current strongly deshields the protons. Any substitution on the benzene ring makes the aromatic protons nonequivalent, and the protons split each other. The peak is, therefore, no longer a singlet and the splitting pattern and their associated coupling...
11.0K
¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

¹H NMR of Conformationally Flexible Molecules: Temporal Resolution

1.3K
At room temperature, the chair conformer of cyclohexane undergoes rapid ring flipping between two equivalent chair conformers at a rate of approximately 105 times per second. These two chair conformers are in equilibrium. The rapid ring flipping results in the interconversion of the axial proton to an equatorial proton and an equatorial to the axial proton. Such interconversions are too rapid and cannot be detected on the NMR timescale. Hence, the NMR spectrometer cannot distinguish between the...
1.3K
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

12.1K
According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).
12.1K
Structure of Benzene: Kekulé Model01:07

Structure of Benzene: Kekulé Model

11.6K
In 1865, August Kekule suggested the structure of benzene according to the structural theory of organic chemistry based on the three assertions—formula of benzene is C6H6, all the hydrogens of benzene are equivalent, and each carbon must have four bonds due to its tetravalency.
He proposed that benzene has a cyclic structure of six carbon atoms attached to one hydrogen atom each, with three alternating pi bonds.
11.6K
Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism01:18

Benzene to 1,4-Cyclohexadiene: Birch Reduction Mechanism

2.6K
Birch reduction uses solvated electrons as reducing agents. The reaction converts benzene to 1,4-cyclohexadiene. The reaction proceeds by the transfer of a single electron to the ring to form a benzene radical anion. This anion is highly basic—it abstracts a proton from the alcohol to form a cyclohexadienyl radical. Another single electron transfer gives the cyclohexadienyl anion. A proton transfer from the alcohol forms 1,4-cyclohexadiene. Since this reduction occurs via radical anion...
2.6K
¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR01:15

¹H NMR of Conformationally Flexible Molecules: Variable-Temperature NMR

1.7K
The axial and equatorial protons in cyclohexane can be distinguished by performing a variable-temperature NMR experiment. In this process, except for one proton, the remaining eleven protons are replaced by deuterium. The deuterium substitution avoids the possible peak splitting caused by the spin-spin coupling between the adjacent protons. The remaining proton flips between the axial and equatorial positions.
1.7K

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Ultrafast Time-resolved Near-IR Stimulated Raman Measurements of Functional &#960;-conjugate Systems
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Probing Benzene in a New Way:  High-Resolution Time-resolved Rotational Spectroscopy†.

Christoph Riehn1, Andreas Weichert1, Bernhard Brutschy1

  • 1Institut für Physikalische und Theoretische Chemie, Johann Wolfgang Goethe-Universität Frankfurt/Main, Marie-Curie-Strasse 11, D-60439 Frankfurt/Main, Germany.

The Journal of Physical Chemistry. A
|October 2, 2025
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Precise rotational constants for benzene were measured using time-resolved rotational spectroscopy. This advancement establishes benzene as a benchmark for high-resolution rotational coherence spectroscopy, enabling future studies on molecular structure.

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Area of Science:

  • Molecular Spectroscopy
  • Quantum Chemistry
  • Physical Chemistry

Background:

  • Accurate molecular structure determination is crucial for understanding chemical properties.
  • Benzene is a fundamental aromatic molecule with significant implications in chemistry.
  • High-resolution rotational spectroscopy provides detailed information about molecular dynamics.

Purpose of the Study:

  • To precisely determine the rotational constants of benzene in its ground and electronically excited states.
  • To establish benzene as a molecular benchmark for advanced spectroscopic techniques.
  • To explore the potential of rotational coherence spectroscopy for studying molecular vibrations and structure.

Main Methods:

  • Utilizing time-resolved rotational spectroscopy to probe molecular rotational states.
  • Achieving a relative uncertainty of 10^-5 for rotational constants.
  • Comparing obtained values with existing data from rotationally resolved optical spectroscopy.

Main Results:

  • Precise rotational constants for benzene were successfully obtained for both ground and excited electronic states.
  • The measured constants exhibit excellent agreement with established optical spectroscopy data.
  • The study validates the high precision achievable with time-resolved rotational spectroscopy.

Conclusions:

  • Benzene serves as a reliable molecular benchmark for high-resolution rotational coherence spectroscopy.
  • This spectroscopic method holds promise for future investigations into the influence of vibrations on molecular equilibrium structures.
  • The findings pave the way for studying medium-sized molecules with unprecedented detail.