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Related Concept Videos

Five-Membered Heterocyclic Aromatic Compounds: Overview01:13

Five-Membered Heterocyclic Aromatic Compounds: Overview

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, respectively.
Aromatic Hydrocarbon Cations: Structural Overview01:18

Aromatic Hydrocarbon Cations: Structural Overview

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 with both...
Basicity of Heterocyclic Aromatic Amines01:25

Basicity of Heterocyclic Aromatic Amines

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).
Nomenclature of Aromatic Compounds with Multiple Substituents01:11

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When more than one substituent is present on the benzene ring, the IUPAC nomenclature depends on the number of substituents present.
For disubstituted benzene derivatives, with two groups attached to the benzene ring, three constitutional isomers are possible. For example, consider dimethyl benzene, often called xylene, where the second methyl group can be substituted at the second, third, or fourth carbon. The relative position of the substituents is represented by prefixes ortho, meta, or...
Hybridization of Atomic Orbitals II03:35

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sp3d and sp3d 2 Hybridization
Structure of Benzene: Molecular Orbital Model01:18

Structure of Benzene: Molecular Orbital Model

According to the molecular orbital (MO) model, benzene has a planar structure with a regular hexagon of six sp2 hybridized carbons. As shown in Figure 1, each carbon is bonded to three other atoms with C–C–C and H–C–C bond angles of 120°. The C–H bond length is 109 pm, and the C–C bond length is 139 pm which is midway between the single bond length of sp3 hybridized carbons (154 pm) and sp2 hybridized carbons (133 pm).

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Microwave-Assisted Preparation of 1-Aryl-1H-pyrazole-5-amines
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Published on: June 23, 2019

2-Ethyl-3,5,6-triphenyl-pyrazine.

N Anuradha1, A Thiruvalluvar, S Chitra

  • 1Postgraduate Research Department of Physics, Rajah Serfoji Government College (Autonomous), Thanjavur 613 005, Tamilnadu, India.

Acta Crystallographica. Section E, Structure Reports Online
|November 6, 2012
PubMed
Summary
This summary is machine-generated.

This study reveals significant non-planarity in the pyrazine ring of a C24H20N2 molecule, described as a flattened twist-boat conformation. Steric crowding is the likely cause of this distortion in the crystal structure.

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Area of Science:

  • Organic Chemistry
  • Crystallography

Background:

  • Molecular structure determination is crucial for understanding chemical properties.
  • Non-planar conformations can arise from steric hindrance and influence molecular interactions.

Purpose of the Study:

  • To elucidate the three-dimensional structure of the C24H20N2 molecule.
  • To investigate the conformational characteristics of the pyrazine and benzene rings.

Main Methods:

  • Single-crystal X-ray diffraction was employed to analyze the molecular and crystal structure.
  • Detailed analysis of bond lengths, bond angles, and dihedral angles was performed.

Main Results:

  • The pyrazine ring exhibits significant deviation from planarity, adopting a flattened twist-boat conformation.
  • Dihedral angles between adjacent benzene rings and the ethyl-substituted benzene ring were quantified.
  • The ethyl group displays positional disorder within the crystal lattice.

Conclusions:

  • Steric crowding is identified as the probable cause for the observed pyrazine ring distortion.
  • The study provides detailed structural insights into this specific organic molecule.
  • The absence of intermolecular hydrogen bonds was noted in the crystal packing.