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ortho–para-Directing Activators: –CH3, –OH, –⁠NH2, –OCH301:11

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All ortho–para directors, excluding halogens, are activating groups. These groups donate electrons to the ring, making the ring carbons electron-rich. Consequently, the reactivity of the aromatic ring towards electrophilic substitution increases. For instance, the nitration of anisole is about 10,000 times faster than the nitration of benzene. The electron-donating effect of the methoxy group in anisole activates the ortho and para positions on the ring and stabilizes the corresponding...
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The coupling interactions of nuclei across four or more bonds are usually weak, with J values less than 1 Hz. While these are usually not observed in spectra, the presence of multiple bonds along the coupling pathway can result in observable long-range coupling.
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In aromatic compounds, such as benzene, the circulation of (4n + 2) π-electrons sets up a diamagnetic or diatropic ring current around the perimeter of the molecule. This current induces a magnetic field that opposes the external field inside the ring and reinforces it on the outside. The protons in benzene are deshielded and exhibit high chemical shifts in the range 6.5–8.5 ppm. The shielding effect at the center of the ring is evident in complex aromatic molecules, such as...
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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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Transannular S···N interactions in 10-ethynyl-10H-phenothiazine 5-oxide and 5,5-dioxide.

Satoru Umezono1, Satoshi Ikeda, Tsunehisa Okuno

  • 1Department of Material Science and Chemistry, Wakayama University, Sakaedani, Wakayama 640-8510, Japan.

Acta Crystallographica. Section C, Crystal Structure Communications
|December 7, 2013
PubMed
Summary

This study examines oxidation products of 10-ethynyl-10H-phenothiazine, revealing differences in transannular interactions and hydrogen bonding. Compound (2) exhibits stronger intramolecular S···N contact, influencing Csp-H acidity and π-electron density.

Keywords:
10-ethynyl-10H-phenothiazinecrystal structureintramolecular S...N contactoxidation productstransannular S...N interactions

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Area of Science:

  • Organic Chemistry
  • Crystallography
  • Molecular Interactions

Background:

  • Phenothiazine derivatives are relevant in various chemical and pharmaceutical applications.
  • Understanding oxidation products is crucial for predicting compound stability and reactivity.
  • Transannular interactions and hydrogen bonding significantly influence molecular properties.

Purpose of the Study:

  • To investigate the structural and electronic differences between two oxidation products of 10-ethynyl-10H-phenothiazine.
  • To analyze the impact of transannular interactions on intermolecular hydrogen bonding.
  • To correlate observed structural features with the acidity of Csp-H bonds.

Main Methods:

  • Synthesis and characterization of title compounds C14H9NOS (1) and C14H9NO2S (2).
  • Single-crystal X-ray diffraction to determine crystal structures and intermolecular interactions.
  • Analysis of intramolecular S···N distances and Csp-H···O hydrogen bonds.

Main Results:

  • Compounds (1) and (2) were identified as oxidation products of 10-ethynyl-10H-phenothiazine.
  • A shorter intramolecular S···N contact was observed in compound (2) compared to (1).
  • Both compounds exhibit intermolecular Csp-H···O hydrogen bonds, with stronger bonds in (1).

Conclusions:

  • The transannular S···N interaction in (2) increases π-electron density, leading to lower Csp-H acidity.
  • Structural differences, particularly the S···N contact, dictate the strength of hydrogen bonding and Csp-H acidity.
  • These findings provide insights into the structure-property relationships of phenothiazine oxidation products.