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Related Concept Videos

Structure and Nomenclature of Alcohols and Phenols02:23

Structure and Nomenclature of Alcohols and Phenols

Overview
Alcohols are one of the most important functional groups in organic chemistry. The name of alcohol comes from the hydrocarbon from which it is derived. Alcohols are organic molecules containing the functional hydroxyl or –OH group directly bonded to carbon. Phenols have an OH group directly attached to a benzene ring. While alcohols are colorless, phenol is a white crystalline compound with a characteristic "hospital smell" odor.
As with other organic compounds, alcohols and phenols...
Acidity and Basicity of Alcohols and Phenols02:36

Acidity and Basicity of Alcohols and Phenols

Like water, alcohols are weak acids and bases. This is attributed to the polarization of the O–H bond making the hydrogen partially positive. Moreover, the electron pairs on the oxygen atom of alcohol make it both basic and nucleophilic. Protonation of an alcohol converts hydroxide, a poor leaving group, into water—a good one. The two acid–base equilibria corresponding to ethanol are depicted below.
Nomenclature of Primary Amines01:17

Nomenclature of Primary Amines

Primary, secondary, and tertiary amines are compounds consisting of one, two, and three alkyl groups connected to the amino group (–NH2), respectively. As depicted in Figure 1, the common name of the primary amines is obtained by adding the suffix -amine to the alkyl substituent attached to the amino group as the corresponding alkylamine.
¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)01:20

¹³C NMR: Distortionless Enhancement by Polarization Transfer (DEPT)

When proton-coupled carbon-13 spectra are simplified by a broadband proton decoupling technique, structural information about the coupled protons is lost. Distortionless enhancement by polarization transfer (DEPT) is a technique that provides information on the number of hydrogens attached to each carbon in a molecule. While the DEPT experiment utilizes complex pulse sequences, the pulse delay and flip angle are specifically manipulated. The resulting signals have different phases depending on...
IUPAC Nomenclature of Ketones01:09

IUPAC Nomenclature of Ketones

Like aldehydes, ketones are named using IUPAC rules; in this case, by replacing “e” in the name of the longest hydrocarbon chain with “one.” In acyclic ketones, the ketonic carbon is given the lowest locant value. For instance, as shown below, a simple five-carbon ketone is named pentan-2-one, instead of pentan-4-one. IUPAC rules also allow the placing of the locant value before the parent name to give an alternate name, 2-pentanone.
Preparation of Diols and Pinacol Rearrangement01:57

Preparation of Diols and Pinacol Rearrangement

Compounds bearing two hydroxyl groups are known as diols. When the hydroxyl groups are located on adjacent carbon atoms, the diols are called vicinal diols or glycols. Under acidic conditions, vicinal diols undergo a specific reaction called pinacol rearrangement.
The reaction begins with transferring a proton from the acid catalyst to one of the hydroxyl groups, producing an oxonium ion.

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4-(Dimethyl-amino)phenyl phenyl ketone.

Hoong-Kun Fun1, Samuel Robinson Jebas

  • 1X-ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, 11800 USM, Penang, Malaysia.

Acta Crystallographica. Section E, Structure Reports Online
|January 5, 2011
PubMed
Summary

The crystal structure of C(15)H(15)NO reveals significant twisting between its benzene rings. This molecular arrangement is stabilized by various weak intermolecular forces, including C-H⋯O, C-H⋯π, and π-π interactions.

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Area of Science:

  • Crystallography
  • Chemical Physics
  • Materials Science

Background:

  • Understanding molecular conformation and intermolecular forces is crucial for predicting material properties.
  • Crystal structure analysis provides fundamental insights into the solid-state behavior of organic compounds.
  • The title compound, C(15)H(15)NO, presents an interesting case for studying aromatic ring interactions.

Purpose of the Study:

  • To elucidate the three-dimensional crystal structure of the title compound, C(15)H(15)NO.
  • To quantify the dihedral angle between the two benzene rings within the crystal lattice.
  • To identify and characterize the intermolecular interactions stabilizing the crystal structure.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the atomic arrangement.
  • The crystal structure was solved and refined using standard crystallographic software.
  • Intermolecular interactions were analyzed based on geometric criteria and distances.

Main Results:

  • The crystal structure of C(15)H(15)NO was successfully determined.
  • A significant dihedral angle of 47.97(4)° was observed between the two benzene rings.
  • Weak intermolecular interactions, including C-H⋯O, C-H⋯π, and π-π stacking (centroid-centroid distance 3.8493(5) Å), were identified.

Conclusions:

  • The non-planar conformation of the benzene rings influences the packing in the solid state.
  • The identified intermolecular interactions play a key role in the stability of the crystal lattice.
  • This structural information contributes to the understanding of molecular assembly in organic crystals.