Theoretical and Experimental Chemistry

, Volume 25, Issue 1, pp 73–77 | Cite as

X-ray crystallographic and quantum-chemical investigation of tert-butyl hydroperoxide

  • A. Yu. Kosnikov
  • V. L. Antonovskii
  • S. V. Lindeman
  • M. Yu. Antipin
  • Yu. T. Struchkov
  • N. A. Turovskii
  • I. P. Zyat'kov
Brief Communications

Abstract

An MNDO calculation and an x-ray crystallographic investigation of tert-butyl hydroperoxide (I) were undertaken. The two symmetrically independent molecules of (I), which in fact have identical geometric parameters, form infinite chains along the y axis through staggered hydrogen bonds. The chains have local symmetry, described by a noncrystallographic slip plane. The difference between the experimental value of the COOH dihedral angle (average 100°) and the calculated value (128.5°) is most likely due to the formation of intermolecular hydrogen bonds in the crystal, the energies of which (∿30 kJ/mole) are considerably larger than the calculated excess energy of the conformers observed in the crystal (3.4 and 1.9 kJ/ mole).

Keywords

Hydrogen Hydrogen Bond Hydroperoxide Geometric Parameter Dihedral Angle 

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Copyright information

© Plenum Publishing Corporation 1989

Authors and Affiliations

  • A. Yu. Kosnikov
    • 1
    • 2
  • V. L. Antonovskii
    • 1
    • 2
  • S. V. Lindeman
    • 1
    • 2
  • M. Yu. Antipin
    • 1
    • 2
  • Yu. T. Struchkov
    • 1
    • 2
  • N. A. Turovskii
    • 1
    • 2
  • I. P. Zyat'kov
    • 1
    • 2
  1. 1.Institute of Chemical PhysicsAcademy of Sciences of the USSRUSSR
  2. 2.Institute of Heteroorganic CompoundsAcademy of Sciences of the USSRMoscow

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