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Related Concept Videos

Chirality at Nitrogen, Phosphorus, and Sulfur02:30

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...
Nucleophilic Aromatic Substitution: Addition–Elimination (SNAr)01:30

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Nucleophilic substitution in aromatic compounds is feasible in substrates bearing strong electron-withdrawing substituents positioned ortho or para to the leaving group. The reaction proceeds via two steps: the addition of the nucleophile and the elimination of the leaving group.
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Naming Enantiomers02:21

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The naming of enantiomers employs the Cahn–Ingold–Prelog rules that involve assigning priorities to different substituent groups at a chiral center. Each enantiomer, being a distinct molecule, is assigned a unique name by the Cahn–Ingold–Prelog (CIP) rules, also called the R–S system. The prefix R- or S- attached to the chiral centers in an enantiomer is dependent on the spatial arrangement of the four substituents on the chiral center. The R–S system essentially comprises three steps:...
SN2 Reaction: Stereochemistry02:23

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Structure and Nomenclature of Ethers02:28

Structure and Nomenclature of Ethers

Structure and Bonding
Ethers are organic compounds with an ether functional group which is characterized by an oxygen atom connected to two — identical or different — alkyl, aryl, or vinyl groups. The C–O–C linkage in dimethyl ether — the simplest ether — has an approximately tetrahedral bond angle of 110.3 degrees. The oxygen atom is sp3- hybridized, with the C–O distance being about 140 pm.
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Alkylation of β-Diester Enolates: Malonic Ester Synthesis

Malonic ester synthesis is a method to obtain α substituted carboxylic acids from ꞵ-diesters such as diethyl malonate and alkyl halides.

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Related Experiment Video

Updated: Jun 1, 2026

Metabolic Glycoengineering of Sialic Acid Using N-acyl-modified Mannosamines
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Published on: November 25, 2017

N-Saccharinylmethyl ether.

Waseeq Ahmad Siddiqui, Yasmeen Akhtar, Muhammad Akmal

    Acta Crystallographica. Section E, Structure Reports Online
    |May 18, 2011
    PubMed
    Summary
    This summary is machine-generated.

    The crystal structure of a novel benzisothiazole derivative was determined. This molecule features planar ring systems with a specific dihedral angle, stabilized by intermolecular interactions and forming a hydrogen-bonded ring.

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    Published on: July 26, 2018

    Area of Science:

    • Crystallography
    • Supramolecular Chemistry
    • Organic Chemistry

    Background:

    • Benzisothiazole derivatives are important scaffolds in medicinal chemistry and materials science.
    • Understanding the solid-state structure of novel organic molecules is crucial for predicting their properties and designing new compounds.
    • Intermolecular interactions play a significant role in crystal packing and material properties.

    Purpose of the Study:

    • To elucidate the crystal structure of the title molecule, 1,1,1',1'-tetra-oxo-2,2'-(oxydimethyl-ene)bi(1,2-benzothiazol-3-one).
    • To analyze the molecular geometry, including planarity of the benzisothiazole rings and their relative orientation.
    • To identify and characterize the intermolecular interactions stabilizing the crystal lattice.

    Main Methods:

    • Single-crystal X-ray diffraction was employed to determine the three-dimensional crystal structure.
    • Analysis of bond lengths, bond angles, and dihedral angles to describe the molecular conformation.
    • Identification of weak intermolecular interactions, such as C-H⋯O bonds, and hydrogen-bonded ring formation.

    Main Results:

    • The crystal structure of C(16)H(12)N(2)O(7)S(2) was successfully determined.
    • The benzisothiazole ring systems within the molecule were found to be individually planar, with a dihedral angle of 62.76° between their mean planes.
    • The crystal lattice is stabilized by weak intermolecular C-H⋯O interactions, leading to the formation of a hydrogen-bonded 10-membered ring (R(4)(2)(10)) around an inversion center.

    Conclusions:

    • The study provides detailed crystallographic data for a novel benzisothiazole derivative.
    • The observed planarity of the ring systems and the specific dihedral angle offer insights into the molecule's electronic and steric properties.
    • The identified intermolecular interactions highlight the importance of non-covalent forces in the self-assembly of organic crystals.