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Journal of Chemical Crystallography

, Volume 41, Issue 3, pp 386–390 | Cite as

Synthesis and Crystal Structures of α-Phenyl- and α-Trifluoromethyl-α-(2-pyridyl-N-oxide)ethanols and α-Phenyl-α-(2-pyridyl-N-oxide)ethylene

  • Barbara Modec
  • Michel Stephan
ORIGINAL PAPER

Abstract

The X-ray structures of two α-substituted α-(2-pyridyl-N-oxide)ethanols, the α-phenyl- (3a) and α-trifluoromethyl- (3b) derivatives, were determined. On dehydration of 3a, compound 4a was obtained. This study brought a clear proof that the α-(2-pyridyl-N-oxide)ethanols are formed following oxidation with peroxides of their corresponding pyridines. A different molecular packing was observed for the α-trifluoromethyl derivative due to an additional hydrogen bonding. Compound 3a crystallized in the monoclinic space group P 21/n with unit cell parameters a = 5.7416(1) Å, b = 14.3841(4) Å, c = 13.2821(3) Å, β = 94.918(2)°, V = 1092.90(4) Å3, Z = 4, D = 1.308 Mg/m3. Compound 3b crystallized in the triclinic space group P −1 with unit cell parameters a = 6.1209(2) Å, b = 8.1938(4) Å, c = 9.4675(4) Å, α = 73.363(3)°, β = 73.166(3)°, γ = 71.659(3)°, V = 421.32(3) Å3, Z = 2, D = 1.633 Mg/m3. Compound 4a crystallized in the monoclinic space group P 21/n with unit cell parameters a = 9.3579(3) Å, b = 12.7340(3) Å, c = 9.8579(3) Å, β = 117.3249(15)°, V = 1043.63(5) Å3, Z = 4, D = 1.255 Mg/m3.

Graphical Abstract

The X-ray crystal structures of the title α-(2-pyridyl-N-oxide)ethanols were determined bringing a clear proof that these compounds are formed following the oxidation using peroxides of their corresponding pyridines. A different molecular packing was observed for the α-trifluoromethyl derivative due to an additional hydrogen bonding.

Keywords

Pyridine N-oxides α-Trifluoromethylethanols Hydrogen Bonding 

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Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  1. 1.Department of Chemistry and Chemical TechnologyUniversity of LjubljanaLjubljanaSlovenia
  2. 2.Laboratory of Organic and Medicinal ChemistryNational Institute of ChemistryLjubljanaSlovenia
  3. 3.EN→FIST Centre of ExcellenceLjubljanaSlovenia

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