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Related Concept Videos

SN1 Reaction: Mechanism02:25

SN1 Reaction: Mechanism

Kinetic studies of ionization of a tertiary halide in a protic solvent suggest that only the substrate participates in the rate-determining step (slow step). The nucleophile is involved only after the slowest step. The SN1 reaction takes place in a multiple-step mechanism. 
Firstly, the haloalkane ionizes to generate a carbocation intermediate and a halide ion. This heterolytic cleavage is highly endothermic with large activation energy. The ionization of the substrate, facilitated by a polar...
Fast Reactions01:27

Fast Reactions

Fast reactions occurring in times shorter than the time needed to mix reactants pose a unique challenge for investigation. In a liquid-phase continuous-flow system, reactants A and B are swiftly pushed into the mixing chamber, where mixing occurs within 1 ms. The reaction mixture then flows through an observation tube, and one measures light absorption to determine species concentrations at various points of the tube. This method is most appropriate when relatively large volumes of reactants...
SN2 Reaction: Transition State02:26

SN2 Reaction: Transition State

An SN2 reaction of an alkyl halide is a single-step process in which bond formation between the nucleophile and the substrate and bond breaking between the substrate and the halide occurs simultaneously through a transition state without forming an intermediate.
When the nucleophile approaches the electrophilic carbon with its lone pairs, the halide acts as a leaving group and moves away with the electron-pair bonded to the carbon. Dotted partial bonds represent the bonds being formed or broken...
SN1 Reaction: Kinetics02:05

SN1 Reaction: Kinetics

In an SN2 reaction, the reaction rate depends on both the type of nucleophile and the substrate. A hindered tertiary alkyl halide is practically inert to the SN2 mechanism despite using a strong nucleophile.
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Energy to Drive Translocation

Mitochondrial protein import is powered by two distinct energy sources: ATP hydrolysis and electrochemical potential across the inner membrane. Newly synthesized precursors are bound by cytosolic chaperones of the Hsp70 family, which guide them to the import receptors on the mitochondrial surface. Utilizing the energy of ATP hydrolysis, Hsp70 chaperones transfer these precursors to the TOM receptors on the mitochondrial outer membrane.
Generally, polypeptides are unfolded by two distinct...
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Insensitive Nuclei Enhanced by Polarization Transfer (INEPT)

Insensitive Nuclei Enhanced by Polarization Transfer (INEPT) is an advanced Nuclear Magnetic Resonance (NMR) technique specifically designed to detect and enhance the signals of low-abundance nuclei, such as carbon-13 and nitrogen-15, in small molecules. The fundamental principle behind INEPT is the transfer of polarization from a more abundant and highly polarizable nucleus, typically hydrogen-1, to the low-abundance nucleus of interest. This process effectively boosts the NMR signal of the...

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Updated: Jun 1, 2026

Isotopic Effect in Double Proton Transfer Process of Porphycene Investigated by Enhanced QM/MM Method
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Published on: July 19, 2019

Solid-state thiotropolone: an extremely rapid intramolecular proton transfer.

Takahisa Machiguchi1, Toshio Hasegawa, Hideki Saitoh

  • 1Department of Chemistry, Saitama University, Saitama, 338-8570, Japan.

The Journal of Organic Chemistry
|May 26, 2011
PubMed
Summary

Thiotropolone exists in two tautomeric forms, thione and enethiol, which rapidly equilibrate. This tautomerism persists even in the solid state, driven by a dominant intramolecular hydrogen bond.

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Published on: January 19, 2018

Area of Science:

  • Organic Chemistry
  • Solid-State Chemistry
  • Spectroscopy

Background:

  • Thiotropolone is a sulfur-containing organic compound.
  • Understanding the tautomeric behavior of organic molecules is crucial for predicting their reactivity and properties.

Purpose of the Study:

  • To investigate the tautomeric equilibrium of thiotropolone in various states.
  • To determine the influence of temperature and physical state on thiotropolone's structure.

Main Methods:

  • Variable-temperature solution-state Nuclear Magnetic Resonance (NMR) spectroscopy.
  • Solid-state Cross-Polarization Magic Angle Spinning (CP/MAS) Carbon-13 NMR spectroscopy.
  • X-ray crystallography for crystal structure determination.

Main Results:

  • Thiotropolone exhibits rapid tautomeric equilibration between thione and enethiol forms.
  • This tautomerism is observed in solution, molten, and solid states.
  • The enethiol tautomer is favored in the solid state, stabilized by an intramolecular hydrogen bond.
  • Crystal structure analysis reveals near-perpendicular molecular packing.

Conclusions:

  • Thiotropolone exists as a dynamic equilibrium of tautomers, not a single fixed structure.
  • Intramolecular hydrogen bonding plays a significant role in stabilizing the enethiol tautomer in the solid state.
  • NMR and crystallographic data provide a comprehensive understanding of thiotropolone's structural dynamics.