Chiral β-hydroxycarbonyl compounds based on (−)-menthone: structure and behavior in liquid crystalline systems

L. A. Kutulya, L. D. Patsenker, V. V. Vashchenko, V. P. Kuznetsov, V. I. Kulishov, Yu N. Surov, V. V. Kravets

Research output: Contribution to journalArticlepeer-review

5 Scopus citations


It has been established by X-ray structural analysis that 2-(1′-biphenyl-4-yl-1′-hydroxy)methyl- p-menthan-3-one, one of the products of the reaction of (−)-menthone triisopropyloxytitanium enolate with 4-phenylbenzaldehyde, has a 1 R,2 S,4 S,1′S configuration. In crystals, this β-hydroxyketone adopts a chair conformation with equatorial methyl and isopropyl groups and an axial 2-(1′-biphenyl-4-yl-1′-hydroxy)methyl substituent. Unlike the stereoisomeric compound with the 1 R,2 S,4 S,1′S configuration, the exocyclic fragment of which has an intramolecular >C=O...H-O- hydrogen bond in crystals and solutions, in the crystals of the 1 R,2 S,4 S,1′S ketol under study, molecules are linked by a network of cooperative -O-H...O-H...O-H... hydrogen bonds. Based on the results of molecular mechanics calculations and experimental data of1H NMR and IR spectroscopy, conformations of molecules of this compound, which are in equilibrium in solution, have been characterized. Based on data on spatial structures of stereoisomeric β-hydroxyketones and the character of H-bonds formed by these compounds, the characteristic features of the effect of these chiral alloying additives on the supramolecular structure and macroscopic properties of liquid crystalline systems have been interpreted.

Original languageEnglish
Pages (from-to)1200-1209
Number of pages10
JournalRussian Chemical Bulletin
Issue number7
StatePublished - Jul 1995
Externally publishedYes


  • X-ray structural analysis
  • conformational analysis
  • crystal structure
  • hydrogen bond
  • induced cholesteric liquid crystals
  • molecular mechanics
  • molecular structure
  • stereoisomeric 2-(1′-biphenyl-4-yl-1′-hydroxy)methyl- p-menthan-3-ones
  • twisting power


Dive into the research topics of 'Chiral β-hydroxycarbonyl compounds based on (−)-menthone: structure and behavior in liquid crystalline systems'. Together they form a unique fingerprint.

Cite this