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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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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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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.
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Structure and Nomenclature of Thiols and Sulfides02:17

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Thiols and sulfides are sulfur analogs of alcohols and ethers, respectively, where the sulfur atom takes the place of the oxygen atom. Thus, thiols are generally represented as RSH, where R is an alkyl substituent and —SH is the functional group. On the other hand, in sulfides, the central sulfur atom is bonded to two hydrocarbon groups on either side. Depending upon the type of group, sulfides can be either symmetrical or asymmetrical. Both thiols and sulfides display a bent geometry,...
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The basicity of aromatic amines is much weaker than that of aliphatic amines due to the involvement of the lone pair of electrons over the N atom in resonance with the aryl rings. Generally, the electron-donating ability of any substituents on the aryl ring of aromatic amines increases the basicity of the amine by increasing electron density, and hence the availability of lone pair on the nitrogen. On the other hand, electron-withdrawing functional groups on the aryl ring of amines decrease the...
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Sulfides are the sulfur analog of ethers, just as thiols are the sulfur analog of alcohol. Like ethers, sulfides also consist of two hydrocarbon groups bonded to the central sulfur atom. Depending upon the type of groups present, sulfides can be symmetrical or asymmetrical. Symmetrical sulfides can be prepared via an SN2 reaction between 2 equivalents of an alkyl halide and one equivalent of sodium sulfide.
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Pyrazine-2(1H)-thione.

Adrian Olszewski1, Kinga Wzgarda-Raj1

  • 1Department of Physical Chemistry, Faculty of Chemistry, University of Lodz, Pomorska 163/165, 90-236 Lodz, Poland.

Iucrdata
|November 7, 2022
PubMed
Summary
This summary is machine-generated.

Researchers synthesized a novel compound, C4H4N2S, through the reduction and crystallization of 2-mercapto-pyrazine. Molecular analysis revealed its monoclinic crystal structure with specific hydrogen bonding interactions.

Keywords:
2-mercapto­pyrazineHirshfeld surface analysiscrystal structurehydrogen bonds

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Area of Science:

  • Crystallography
  • Organic Chemistry
  • Materials Science

Background:

  • 2-mercapto-pyrazine is a heterocyclic compound with potential applications.
  • Understanding the synthesis and crystal structure of novel derivatives is crucial for chemical research.

Purpose of the Study:

  • To synthesize and characterize a new compound derived from 2-mercapto-pyrazine.
  • To determine the crystal structure and intermolecular interactions of the synthesized compound.

Main Methods:

  • Chemical reduction of 2-mercapto-pyrazine in ethanol.
  • Crystallization in the presence of isonicotinic acid N-oxide.
  • X-ray diffraction analysis to determine crystal structure.

Main Results:

  • Successful synthesis of the title compound C4H4N2S.
  • Determination of monoclinic space group P2.
  • Identification of N-H⋯N and C-H⋯S hydrogen bonds in the crystal lattice.

Conclusions:

  • The study reports a new synthetic route to C4H4N2S.
  • The crystal structure provides insights into intermolecular forces governing the solid state.
  • This work contributes to the understanding of pyrazine derivatives.