Synthesis and structure of bis(3,3-dimethyl-3,4-dihydroisoquinolyl-1) ketoxime

The reaction of bis(3,3-dimethyl-3,4-dihydroisoquinolyl-1)methane with NaNO2 resulted in the formation of bis(3,3-dimethyl-3,4-dihydroisoquinolyl-1) ketoxime (I). The crystal and molecular structure of I was determined (X-ray structure analysis, Enraf-Nonius CAD-4, MoKα-radiation, graphite monochromator, θ/2θ scan, 2θmax = 58°, 4800 unique reflections; a = 10.327(4), b = 9.070(5), and c = 21.62(1) Å; β = 94.02(3)°; V = 2020(1) Å3; Z = 4; and sp. gr. Pn). In the crystal, I exists in the oxime tautomeric form. Two symmetry-independent molecules are bound into a dimer through the intermolecular N = OH⋯N3 cycl hydrogen bond. Both molecules are nonplanar; the dihedral angles between the mean planes of their 3,4-dihydroisoquinoline moieties are 72° and 74°. According to IR and electron absorption spectra, the tautomeric form of compound I is also retained in solutions, and the π-conjugation between the 3,4-dihydroisoquinoline fragments of I is actually absent.

Authors
Sokol V.I.1 , Davydov V.V. 2 , Shklyaev Yu.V.3 , Kartashova I.V. 2 , Sergienko V.S.1 , Zaitsev B.E. 2
Number of issue
3
Language
English
Pages
396-402
Status
Published
Volume
42
Year
1997
Organizations
  • 1 Kurnakov Inst. Gen. and Inorg. Chem., Russian Academy of Sciences, Leninskii pr. 31, Moscow, 117907, Russian Federation
  • 2 University of Peoples' Friendship, ul. Miklukho-Maklaya 6, Moscow, 117198, Russian Federation
  • 3 Institute of Technical Chemistry, Ural Division, Russian Academy of Sciences, Perm, Russian Federation
Date of creation
19.10.2018
Date of change
16.04.2021
Short link
https://repository.rudn.ru/en/records/article/record/735/
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