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Amines to Sulfonamides: The Hinsberg Test01:23

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The Hinsberg test is a method to identify primary, secondary and tertiary amines, named after its pioneer, Oscar Hinsberg. Here, amines are treated with benzenesulfonyl chloride, also known as the Hinsberg reagent, in the presence of an excess of aqueous base, followed by acidification. Based on the nature of the amines, different changes are observed.
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Hydrolysis of acid halides is a nucleophilic acyl substitution reaction in which acid halides react with water to give carboxylic acids. The reaction occurs readily and does not require acid or a base catalyst.
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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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IR and UV–Vis Spectroscopy of Carboxylic Acids01:28

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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,...
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Nitrous acid, a weak acid, is prepared in situ via the reaction of sodium nitrite with a strong acid under cold conditions. This nitrous acid prepared in situ reacts with primary arylamines to form arenediazonium salts. Such reactions are known as diazotization reactions. As shown in Figure 1, the formation of arenediazonium salts begins with the decomposition of nitrous acid in an acidic solution to give nitrosonium ions.
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2D NMR: Heteronuclear Single-Quantum Correlation Spectroscopy (HSQC)01:19

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Heteronuclear single-quantum correlation spectroscopy (HSQC) is a 2D NMR technique that reveals one-bond correlations between hydrogen and a heteronucleus. The HSQC experiment is similar to the heteronuclear correlation experiment (HETCOR) but is more sensitive. In the HSQC spectrum, the proton chemical shift is plotted on the horizontal F2 axis, while the 13C chemical shift is plotted on the vertical F1 axis. The corresponding proton and 13C spectra are also shown. The HSQC contour plot does...
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Structure-Function Analysis of Hydroxy-1,8-Naphthalimide Photoacids for ESPT-Driven H2S Probes.

Trevor Dvorak1, Sunayn Cheku2, Linus Borer1

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Area of Science:

  • Organic Chemistry
  • Analytical Chemistry
  • Biochemistry

Background:

  • Hydroxy-1,8-naphthalimides are photoacidic fluorophores enabling excited-state proton transfer (ESPT).
  • ESPT leads to red-shifted fluorescence, useful for developing sensitive detection probes.
  • Hydrogen sulfide (H2S) is a crucial signaling molecule with implications in various biological processes.

Purpose of the Study:

  • To synthesize and evaluate novel reaction-based fluorescent probes for selective H2S detection.
  • To investigate the structure-activity relationships of hydroxy-1,8-naphthalimide derivatives for H2S sensing.
  • To explore the role of hydroxyl substituent position in modulating probe performance.

Main Methods:

  • Synthesis of four hydroxy-1,8-naphthalimide-based fluorescent probes (L1-L4).
  • Evaluation of probe photophysical properties, including fluorescence emission and ESPT efficiency.
  • Assessment of probe reactivity and selectivity towards H2S and other biologically relevant thiols.

Main Results:

  • Probe sensitivity and emission wavelength were significantly influenced by the hydroxyl group's position.
  • L1 (3-hydroxy) and L3 (4-hydroxy) probes showed distinct fluorescence maxima (617 nm and 550 nm) and rapid H2S reactivity.
  • L3 exhibited enhanced sensitivity due to a more stable naphtholate intermediate; L4 demonstrated high selectivity for H2S over other thiols.

Conclusions:

  • Key structure-activity relationships for naphthalimide-based H2S probes were established.
  • The position of the hydroxyl group is critical for optimizing ESPT, emission, and sensitivity.
  • These findings provide design strategies for developing advanced fluorescent probes for reactive sulfur species detection.