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¹H NMR of Conformationally Flexible Molecules: Temporal Resolution00:52

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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...
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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.
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Luminescence, the emission of light by a substance that has absorbed energy, is a process that involves the interaction of molecules with light. The energy-level diagram, or Jablonski diagram, is a graphical representation of these interactions, illustrating the various states and transitions a molecule can undergo. In a typical Jablonski diagram, the lowest horizontal line represents the ground-state energy of the molecule, which is usually a singlet state. This state represents the energies...
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Sigmatropic rearrangements are a class of pericyclic reactions in which a σ bond migrates from one part of a π system to another. These are intramolecular rearrangements where the total number of σ and π bonds remain unchanged.
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Light-Induced Conformational Switching of 2-Formyl Benzothiazole in Low Temperature Inert Gas Matrices.

Piyush Kumar1, Gaurav Jhaa1, Shabana Butt1

  • 1Department of Chemical Sciences, Indian Institute of Science Education and Research (IISER) Mohali, Manauli, India.

Chemphyschem : a European Journal of Chemical Physics and Physical Chemistry
|April 27, 2026
PubMed
Summary

Photochemical reactions of 2-formyl benzothiazole (2FBT) were studied. Light exposure primarily caused conformational changes, with ring-opening occurring only after prolonged irradiation, suggesting C-S bond cleavage is the preferred pathway.

Keywords:
conformational changedensity functional theoryinfrared spectroscopymatrix isolationphotochemistry

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Area of Science:

  • Photochemistry
  • Organic Chemistry
  • Spectroscopy

Background:

  • Benzothiazole derivatives are widely used in various applications.
  • The photolabile C-S bond in benzothiazoles allows for ring-opening under photochemical conditions.
  • Aldehyde functionalization can influence photochemical behavior, leading to conformational changes.

Purpose of the Study:

  • To investigate the photochemical outcome of 2-formyl benzothiazole (2FBT) under cryogenic conditions.
  • To elucidate the competitive photochemical pathways: conformational change versus ring-opening.
  • To determine the preferred mechanistic channel for 2FBT photochemistry.

Main Methods:

  • Matrix isolation spectroscopy at 4 K in argon and nitrogen.
  • UV irradiation at λ=254 nm.
  • Computational studies using CAM-B3LYP/6-311++G(d, p) for potential energy surface calculations.

Main Results:

  • Deposition isolated the (s)-trans conformer of 2FBT.
  • Irradiation induced a conformational change to the (s)-cis conformer.
  • Ring-opening products were observed only upon prolonged irradiation.
  • Computational analysis revealed two pathways: C-C bond rotation and C-S bond cleavage.
  • C-S bond cleavage was identified as the preferred pathway due to lower energy barriers and excited state intermediate.

Conclusions:

  • 2-formyl benzothiazole primarily undergoes light-induced conformational changes rather than immediate ring-opening.
  • The C-S bond cleavage pathway is favored computationally and experimentally under cryogenic conditions.
  • Understanding these photochemical pathways is crucial for designing benzothiazole-based materials with controlled light responsiveness.