Structural characterization of the crystalline diastereomeric complexes of enantiopure dimethylacridino-18-crown-6 ether and the enantiomers of 1-(1-naphthyl)ethylamine hydrogen perchlorate

Tünde Tóth, Tamás Németh, Ibolya Leveles, B. Vértessy, P. Huszthy

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3 Citations (Scopus)

Abstract

This paper describes the X-ray crystal structure of the diastereomeric complexes formed by enantiopure dimethyl-substituted acridino-18-crown-6 ether (R,R)-1 and the enantiomers of 1-(1-naphthyl)ethylammonium perchlorate. We found that the heterochiral complex (R,R)-1–(S)-1-NEA is more stable than the homochiral one (R,R)-1–(R)-1-NEA. In the case of the heterochiral complex, the X-ray studies revealed a strong intermolecular π–π interaction between the naphthyl unit and the acridine moiety. However, in the case of the homochiral complex, π–π interaction was not found. We suggest that the existence or absence of the π–π interaction and the difference in steric repulsions in the diastereomers is responsible for the enantiomeric discrimination.

Original languageEnglish
Pages (from-to)1-8
Number of pages8
JournalStructural Chemistry
DOIs
Publication statusAccepted/In press - Aug 11 2016

Fingerprint

hydrogen perchlorate
Enantiomers
enantiomers
Ether
Hydrogen
ethers
Crystalline materials
Acridines
X rays
Crystal structure
interactions
perchlorates
discrimination
x rays
crystal structure
perchlorate
1-(1-naphthyl)ethylamine
18-crown-6

Keywords

  • 1-(1-naphthyl)ethylammonium perchlorate
  • Acridine
  • Crown ether
  • Diastereomeric complexes
  • Hydrogen bonding
  • X-ray analysis
  • π–π interaction

ASJC Scopus subject areas

  • Condensed Matter Physics
  • Physical and Theoretical Chemistry

Cite this

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title = "Structural characterization of the crystalline diastereomeric complexes of enantiopure dimethylacridino-18-crown-6 ether and the enantiomers of 1-(1-naphthyl)ethylamine hydrogen perchlorate",
abstract = "This paper describes the X-ray crystal structure of the diastereomeric complexes formed by enantiopure dimethyl-substituted acridino-18-crown-6 ether (R,R)-1 and the enantiomers of 1-(1-naphthyl)ethylammonium perchlorate. We found that the heterochiral complex (R,R)-1–(S)-1-NEA is more stable than the homochiral one (R,R)-1–(R)-1-NEA. In the case of the heterochiral complex, the X-ray studies revealed a strong intermolecular π–π interaction between the naphthyl unit and the acridine moiety. However, in the case of the homochiral complex, π–π interaction was not found. We suggest that the existence or absence of the π–π interaction and the difference in steric repulsions in the diastereomers is responsible for the enantiomeric discrimination.",
keywords = "1-(1-naphthyl)ethylammonium perchlorate, Acridine, Crown ether, Diastereomeric complexes, Hydrogen bonding, X-ray analysis, π–π interaction",
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T1 - Structural characterization of the crystalline diastereomeric complexes of enantiopure dimethylacridino-18-crown-6 ether and the enantiomers of 1-(1-naphthyl)ethylamine hydrogen perchlorate

AU - Tóth, Tünde

AU - Németh, Tamás

AU - Leveles, Ibolya

AU - Vértessy, B.

AU - Huszthy, P.

PY - 2016/8/11

Y1 - 2016/8/11

N2 - This paper describes the X-ray crystal structure of the diastereomeric complexes formed by enantiopure dimethyl-substituted acridino-18-crown-6 ether (R,R)-1 and the enantiomers of 1-(1-naphthyl)ethylammonium perchlorate. We found that the heterochiral complex (R,R)-1–(S)-1-NEA is more stable than the homochiral one (R,R)-1–(R)-1-NEA. In the case of the heterochiral complex, the X-ray studies revealed a strong intermolecular π–π interaction between the naphthyl unit and the acridine moiety. However, in the case of the homochiral complex, π–π interaction was not found. We suggest that the existence or absence of the π–π interaction and the difference in steric repulsions in the diastereomers is responsible for the enantiomeric discrimination.

AB - This paper describes the X-ray crystal structure of the diastereomeric complexes formed by enantiopure dimethyl-substituted acridino-18-crown-6 ether (R,R)-1 and the enantiomers of 1-(1-naphthyl)ethylammonium perchlorate. We found that the heterochiral complex (R,R)-1–(S)-1-NEA is more stable than the homochiral one (R,R)-1–(R)-1-NEA. In the case of the heterochiral complex, the X-ray studies revealed a strong intermolecular π–π interaction between the naphthyl unit and the acridine moiety. However, in the case of the homochiral complex, π–π interaction was not found. We suggest that the existence or absence of the π–π interaction and the difference in steric repulsions in the diastereomers is responsible for the enantiomeric discrimination.

KW - 1-(1-naphthyl)ethylammonium perchlorate

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KW - Crown ether

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KW - X-ray analysis

KW - π–π interaction

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