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Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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Heterocyclic amines, where the N atom is a part of an alicyclic system, are similar in basicity to alkylamines. Interestingly, the heterocyclic amine having a nitrogen atom as part of an aromatic ring has much less basicity than its corresponding alicyclic counterpart. For this reason, as presented in Figure 1, piperidine (pKb = 2.8) is significantly more basic than pyridine (pKb = 8.8).
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Nomenclature of Aryl and Heterocyclic Amines01:10

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The simplest aromatic amine is phenylamine, which contains an –NH2 functionality directly attached to an aromatic ring. The name aniline is designated for this skeleton. As shown in Figure 1, the common names of the functionalized anilines involve prefixes ortho-, meta-, and para- to indicate the substitution position. Different functionalized aniline derivatives also have notable trivial names.
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Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

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Heterocyclic aromatic compounds are cyclic compounds that are aromatic and have one or more heteroatoms—atoms other than carbon, in the ring. Depending upon the number of atoms present in the ring, they can be either five or six-membered. Examples of five-membered heterocyclic aromatic compounds include pyrrole, furan, thiophene, and imidazole. Pyrrole consists of one nitrogen atom having one lone pair of electrons. Furan and thiophene have one oxygen and one sulfur heteroatom,...
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Nomenclature of Alkynes02:39

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Alkynes are unsaturated hydrocarbons characterized by the presence of carbon-carbon triple bonds and have a general formula CnH2n-2. The nomenclature of alkynes follows a set of rules similar to alkanes and alkenes; however, alkynes bear the suffix "-yne" instead of "-ane" or "-ene." There are two approaches to naming alkynes:
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Aromatic Hydrocarbon Cations: Structural Overview01:18

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Cycloheptatriene is a neutral monocyclic unsaturated hydrocarbon that consists of an odd number of carbon atoms and an intervening sp3 carbon in the ring. The three double bonds in the ring correspond to 6 π electrons, which is a Huckel number, and therefore satisfies the criteria of 4n + 2 π electrons. However, the intervening sp3 carbon disrupts the continuous overlap of p orbitals. As a result, cycloheptatriene is not aromatic.
Removing one hydrogen from the intervening CH2 group...
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Neutral hydrocarbons like cyclopentadiene with an odd number of carbon atoms and one intervening CH2 group in the ring are not aromatic. Cyclopentadiene with 4 π electrons does not satisfy the 4n + 2 π electron rule. Additionally, the intervening CH2 group is sp3 hybridized and lacks a vacant p orbital, thereby interrupting the overlap of p orbitals in a continuous manner and preventing the delocalization of π electrons throughout the ring.
Due to the absence of continuous...
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Microwave-assisted Intramolecular Dehydrogenative Diels-Alder Reactions for the Synthesis of Functionalized Naphthalenes/Solvatochromic Dyes
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4-(Naphthalen-1-yl)pyridine.

Antje Vetter1, Wilhelm Seichter1, Edwin Weber1

  • 1Institut für Organische Chemie, TU Bergakademie Freiberg, Leipziger Strasse 29, D-09596 Freiberg/Sachsen, Germany.

Acta Crystallographica. Section E, Structure Reports Online
|March 15, 2014
PubMed
Summary
This summary is machine-generated.

This study reveals the crystal structure of a C15H11N compound, highlighting its unique π-π stacking and C-H⋯π interactions. These molecular interactions form a distinctive herringbone supramolecular architecture.

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Syntheses, Crystallization, and Spectroscopic Characterization of 3,5-Lutidine N-Oxide Dehydrate
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Area of Science:

  • Crystallography
  • Supramolecular Chemistry
  • Organic Chemistry

Background:

  • Understanding molecular interactions is crucial for designing novel materials.
  • Crystal engineering relies on predicting and controlling intermolecular forces.
  • Aromatic compounds exhibit diverse packing motifs in the solid state.

Purpose of the Study:

  • To elucidate the crystal structure of the C15H11N compound.
  • To investigate the intermolecular interactions governing its solid-state arrangement.
  • To characterize the supramolecular architecture formed by the molecule.

Main Methods:

  • Single-crystal X-ray diffraction was employed to determine the molecular structure and packing.
  • Analysis of intermolecular contacts, including π-π stacking and C-H⋯π interactions, was performed.
  • Geometric parameters such as dihedral angles and centroid-centroid distances were measured.

Main Results:

  • The crystal structure of C15H11N was determined, revealing a dihedral angle of 72.9° between its aromatic moieties.
  • Significant π-π stacking interactions between pyridine rings were observed, with a centroid-centroid distance of 3.772 Å.
  • C-H⋯π contacts between the pyridine and naphthalene units contribute to a herringbone supramolecular architecture.

Conclusions:

  • The C15H11N compound self-assembles through a combination of π-π stacking and C-H⋯π interactions.
  • These interactions lead to a well-defined herringbone supramolecular structure.
  • The findings provide insights into the crystal engineering of nitrogen-containing aromatic compounds.