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Acetoacetic ester synthesis is a method to obtain ketones from alkyl halides and β-keto esters. The reaction occurs in the presence of an alkoxide base that abstracts the acidic proton of the β-keto esters. The step results in an enolate ion which is doubly stabilized. The enolate then reacts with an alkyl halide via the SN2 process to produce an alkylated ester intermediate with a new C–C bond. The hydrolysis of the intermediate, followed by acidification, results in an...
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The acidic strength of hydrocarbons follows the order: Alkynes > Alkenes > Alkanes. The strength of an acid is commonly expressed in units of pKa — the lower the pKa, the stronger the acid. Among the hydrocarbons, terminal alkynes have lower pKa values and are, therefore, more acidic. For example, the pKa values for ethane, ethene, and acetylene are 51, 44, and 25, respectively, as shown here.
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This study details the crystal structure of a novel indole compound (C13H15NO2). Molecular analysis reveals specific dihedral angles and hydrogen bonding that form helical chains in the crystal lattice.

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Molecular Structure

Background:

  • Indole derivatives are prevalent in pharmaceuticals and natural products.
  • Understanding the precise molecular arrangement is crucial for predicting chemical properties and biological activity.

Purpose of the Study:

  • To elucidate the three-dimensional crystal structure of the title compound, C13H15NO2.
  • To analyze the spatial arrangement of the acetate group relative to the indole ring system.
  • To investigate intermolecular interactions, such as hydrogen bonding, within the crystal lattice.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and dihedral angles provided detailed geometric information.
  • Identification and analysis of intermolecular interactions, including hydrogen bonds, were performed.

Main Results:

  • The crystal structure of C13H15NO2 was successfully determined.
  • A significant dihedral angle of 62.35(13)° was observed between the acetate group and the indole ring system.
  • N-H⋯O hydrogen bonds were identified, leading to the formation of helical chains propagating along the [010] direction.

Conclusions:

  • The study provides a detailed crystallographic description of the indole derivative C13H15NO2.
  • The observed helical chain formation due to hydrogen bonding offers insights into crystal packing and potential solid-state properties.
  • This structural information can serve as a foundation for further research into the compound's chemical reactivity and applications.