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Alkyl Halides02:45

Alkyl Halides

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Structural Properties
Alkyl halides are halogen-substituted alkanes wherein one or more hydrogen atoms of an alkane is replaced by a halogen atom such as fluorine, chlorine, bromine, or iodine. The carbon atom in an alkyl halide is bonded to the halogen atom, which is sp3-hybridized and exhibits a tetrahedral shape.
Unlike alkyl halides, compounds in which a halogen atom is bonded to an sp2 -hybridized carbon atom of a carbon-carbon double bond (C=C) are called vinyl halides. Whereas aryl...
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Halogenation of Alkenes02:46

Halogenation of Alkenes

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Halogenation is the addition of chlorine or bromine across the double bond in an alkene to yield a vicinal dihalide. The reaction occurs in the presence of inert and non-nucleophilic solvents, such as methylene chloride, chloroform, or carbon tetrachloride.
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
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Acid-Catalyzed α-Halogenation of Aldehydes and Ketones01:21

Acid-Catalyzed α-Halogenation of Aldehydes and Ketones

3.1K
By replacing an α-hydrogen with a halogen, acid-catalyzed α-halogenation of aldehydes or ketones yields a monohalogenated product
In the first step of the mechanism, the acid protonates the carbonyl oxygen resulting in a resonance-stabilized cation, which subsequently loses an α-hydrogen to form an enol tautomer. The C=C bond in an enol is highly nucleophilic because of the electron-donating nature of the –OH group. Consequently, the double bond attacks an electrophilic...
3.1K
Radical Substitution: Halogenation of Alkanes and Alkyl Substituents01:27

Radical Substitution: Halogenation of Alkanes and Alkyl Substituents

7.6K
In the presence of heat or light, alkanes react with molecular halogens to form alkyl halides by a substitution reaction called radical halogenation. This reaction has three steps: initiation, propagation, and termination, as seen in the radical chlorination of methane to produce methyl chloride.
In the initiation step of the reaction, the chlorine molecule undergoes homolytic cleavage in the presence of light or heat, forming two highly reactive chlorine radicals. Propagation occurs in two...
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Gas Chromatography: Types of Detectors-I01:21

Gas Chromatography: Types of Detectors-I

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There are different types of detectors used in gas chromatography, each with its own specific properties that make it suitable for detecting certain types of analytes. The most commonly used detectors in GC are thermal conductivity detector (TCD), flame ionization detector (FID), and electron capture detector (ECD).
TCD is the earliest and most widely used detector that operates by measuring the changes in the thermal conductivity of the carrier gas. When a sample compound enters the detector,...
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Gas Chromatography: Types of Detectors-II01:19

Gas Chromatography: Types of Detectors-II

1.5K
In gas chromatography, different detectors are employed to meet specific analytical needs. These detectors are often categorized based on their detection mechanisms and the types of compounds they are best suited to analyze. Thermal Conductivity Detectors (TCD), Flame Ionization Detectors (FID), and Electron Capture Detectors (ECD) represent common categories, each with unique operating principles and applications. However, beyond these, several other detectors are designed for more specialized...
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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Fluorescent alpha-cyclodextrin as a chemosensor for halomethanes.

Hiroshi Ikeda1, Akihiko Ueno

  • 1Department of Bioengineering, Graduate School of Bioscience and Biotechnology, Tokyo Institute of Technology, 4259-B44 Nagatsuta-cho, Midori-ku, Yokohama 226-8501, Japan. hikeda@bio.titech.ac.jp

Chemical Communications (Cambridge, England)
|July 9, 2009
PubMed
Summary

A novel fluorescent sensor, NBDamine-appended alpha-cyclodextrin, selectively detects perhalogenated methanes. This selectivity arises from unique multisite interactions between the analyte and the sensor molecule.

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Area of Science:

  • Analytical Chemistry
  • Supramolecular Chemistry

Background:

  • Development of selective fluorescent chemosensors is crucial for environmental monitoring and chemical analysis.
  • Perhalogenated methanes pose environmental risks and require sensitive detection methods.

Purpose of the Study:

  • To synthesize and characterize a new fluorescent chemosensor for the selective detection of perhalogenated methanes.
  • To investigate the interaction mechanism between the chemosensor and perhalogenated methanes.

Main Methods:

  • Synthesis of NBDamine-appended alpha-cyclodextrin.
  • Fluorescence spectroscopy for sensing studies.
  • Analysis of host-guest interactions.

Main Results:

  • The NBDamine-appended alpha-cyclodextrin demonstrated high selectivity towards perhalogenated methanes.
  • Multisite interactions were identified as the key mechanism for selective binding.
  • The chemosensor exhibited significant fluorescence changes upon binding.

Conclusions:

  • NBDamine-appended alpha-cyclodextrin is a promising fluorescent chemosensor for perhalogenated methanes.
  • The study highlights the potential of cyclodextrin-based sensors for specific analyte recognition.