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Related Concept Videos

Preparation of Acid Anhydrides01:07

Preparation of Acid Anhydrides

3.2K
One of the methods for preparing symmetrical or unsymmetrical acid anhydrides involves the treatment of acid chlorides with the sodium salt of carboxylic acids. The reaction proceeds via a nucleophilic acyl substitution.
The carboxylate ion acts as a nucleophile that attacks the carbonyl carbon of the acid chloride to form a tetrahedral intermediate. Subsequently, the re-formation of the carbonyl group with the loss of the chloride ion as a leaving group leads to the formation of an acid...
3.2K
Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides01:16

Nomenclature of Carboxylic Acid Derivatives: Acid Halides, Esters, and Acid Anhydrides

4.4K
Naming Acid Halides
The IUPAC and common names of acid halides are derived from the corresponding carboxylic acids, by changing “ic acid” to “yl halide.” For example, as shown below, the IUPAC name ethanoyl chloride is derived from ethanoic acid, and the common name, acetyl chloride, is obtained from acetic acid.
4.4K
[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction01:16

[4+2] Cycloaddition of Conjugated Dienes: Diels–Alder Reaction

10.3K
The Diels–Alder reaction is an example of a thermal pericyclic reaction between a conjugated diene and an alkene or alkyne, commonly referred to as a dienophile. The reaction involves a concerted movement of six π electrons, four from the diene and two from the dienophile, forming an unsaturated six-membered ring. As a result, these reactions are classified as [4+2] cycloadditions.
10.3K
Preparation and Reactions of Thiols02:33

Preparation and Reactions of Thiols

6.3K
Thiols are prepared using the hydrosulfide anion as a nucleophile in a nucleophilic substitution reaction with alkyl halides. For instance, bromobutane reacts with sodium hydrosulfide to give butanethiol.
6.3K
Reactions of Acid Anhydrides01:19

Reactions of Acid Anhydrides

4.2K
The reactions of acid anhydrides are analogous to the reactions of acid chlorides and proceed via a nucleophilic acyl substitution. They only differ in the identity of the leaving group. During an acid chloride reaction, the leaving group is a chloride ion, and the by-product is hydrochloric acid. However, in an acid anhydride reaction, the leaving group is a carboxylate ion, and the by-product is a carboxylic acid.
4.2K
Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization01:13

Intramolecular Claisen Condensation of Dicarboxylic Esters: Dieckmann Cyclization

2.4K
Dieckmann cyclization is an intramolecular Claisen condensation of diesters. The reaction occurs in the presence of a base and generates a cyclic β-ketoester as the final product. Commonly, 1, 6 and 1, 7-diesters are preferred substrates for the reaction since the generated five, and six-membered cyclic β-keto esters are particularly more stable.
2.4K

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Updated: Jul 16, 2025

Modification and Functionalization of the Guanidine Group by Tailor-made Precursors
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Modification and Functionalization of the Guanidine Group by Tailor-made Precursors

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5,6-Di-hydro-1,4-dithiine-2,3-di-carb-oxy-lic anhydride.

Olivia Bullock1, Sarah Rice1, Marcus R Bond1

  • 1Department of Chemistry and Physics, Southeast Missouri State University, Cape Girardeau, MO 63701, USA.

Iucrdata
|September 11, 2023
PubMed
Summary

The crystal structure of 2,3-dihydro-1,4-dithiino[2,3-c]furan-5,7-dione was determined and found to align with density functional theory (DFT) calculations. Molecular packing is driven by dipole-dipole interactions, unlike related compounds.

Keywords:
anhydridecrystal structuredithiinefused ringheterocycle

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Computational Chemistry

Background:

  • The study investigates the structural and packing characteristics of 2,3-dihydro-1,4-dithiino[2,3-c]furan-5,7-dione.
  • Comparison with phthalamide, thieno, and hydroxy analogs provides context for its unique structural features.

Purpose of the Study:

  • To determine the precise molecular geometry of the title compound through experimental methods.
  • To compare the observed structure with theoretical calculations and related compounds.
  • To elucidate the intermolecular interactions governing the crystal packing.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the solid-state structure.
  • Density functional theory (DFT) calculations were performed for comparative structural analysis.

Main Results:

  • The observed molecular geometry closely matches DFT-calculated values and those of structural analogs.
  • Key structural features include a specific S-C-C-S torsion angle and differential S-C bond lengths to sp2 and sp3 hybridized carbon atoms.
  • The crystal packing is characterized by head-to-tail molecular rows, driven by optimized dipole-dipole interactions, lacking directed intermolecular interactions seen in analogs.

Conclusions:

  • The study provides a detailed structural characterization of 2,3-dihydro-1,4-dithiino[2,3-c]furan-5,7-dione.
  • The findings highlight the role of dipole-dipole interactions in the absence of directed intermolecular forces for this compound's packing.
  • The agreement between experimental and computational data validates the employed methods for structural analysis.