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Title: Molecular and crystal structure of bis-quinolizidine immonium salts, II:. delta. /sup 1(6)/-dehydrosparteinium monoperchlorate

Abstract

..delta../sup 1(6)/-Dehydrosparteinium monoperchlorate, (C/sub 15/H/sub 25/N/sub 2/)/sup +/ x ClO/sub 4//sup -/, is orthorhombic: P2/sub 1/2/sub 11/, a = 12.473(2), b = 24.292(3), c = 10.835(1) A, V/sub c/ = 3353.7(9) A/sup 3/, Z = 8, D/sub x/ = 1.32, D/sub m/ = 1.32 g cm/sup -3/, ..mu..(Cu K..cap alpha..) = 20.7 cm/sup -1/. The final R was 0.097 for 2091 observed counter reflections. A partial disorder of the crystal structure has been observed. The two independent perchlorate anions are orientationally disordered, and the peripheral atoms in the cation skeletons have large temperature factors due both to conformational disorder of rings A and to disordered orientations of the whole cations alike. In rings A, atoms C(3) and C(4), trans-annular to the immonium bond, are disordered to a different extent in each of the two independent cations. Rings B, C, and D have sofa (distorted towards half-chair), chair, and chair conformations, respectively. The quinolizidinium and quinolizidine moieties have planar and cis configurations, respectively. The title compound was obtained from ..delta../sup 5/-dehydrosparteine, the product of mercuric acetate dehydrogenation of sparteine at room temperature. From /sup 13/C NMR measurements in /sup 2/H/sub 2/O and in DMSO/sup 2/H/sub 6/ it is evident that, inmore » solution, the molecular geometry with chair/chair cis-ring fusion within the quinolizidine moiety is present, as was in the crystalline state by X-ray analysis.« less

Authors:
; ; ;
Publication Date:
Research Org.:
Adam Mickiewicz Univ., Poznan, Poland
OSTI Identifier:
6321396
Resource Type:
Journal Article
Journal Name:
J. Crystallogr. Spectrosc. Res.; (United States)
Additional Journal Information:
Journal Volume: 16:2
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY; 36 MATERIALS SCIENCE; 74 ATOMIC AND MOLECULAR PHYSICS; PERCHLORATES; MOLECULAR STRUCTURE; NMR SPECTRA; ORTHORHOMBIC LATTICES; ALKALOIDS; BOND ANGLE; BOND LENGTHS; CARBON 13; CHEMICAL SHIFT; CONFORMATIONAL CHANGES; DEUTERIUM COMPOUNDS; DMSO; ELECTRON SPECTRA; HYPERFINE STRUCTURE; INFRARED SPECTRA; ISOTOPIC EXCHANGE; MASS SPECTRA; ORDER PARAMETERS; ORDER-DISORDER TRANSFORMATIONS; QUINOLINES; SPIN; STRUCTURAL CHEMICAL ANALYSIS; SYNTHESIS; X-RAY DIFFRACTION; ANGULAR MOMENTUM; AROMATICS; AZAARENES; AZINES; CARBON ISOTOPES; CHLORINE COMPOUNDS; COHERENT SCATTERING; CRYSTAL LATTICES; CRYSTAL STRUCTURE; DIFFRACTION; DIMENSIONS; EVEN-ODD NUCLEI; HALOGEN COMPOUNDS; HETEROCYCLIC COMPOUNDS; HYDROGEN COMPOUNDS; ISOTOPES; LENGTH; LIGHT NUCLEI; NUCLEI; ORGANIC COMPOUNDS; ORGANIC NITROGEN COMPOUNDS; ORGANIC SULFUR COMPOUNDS; OXYGEN COMPOUNDS; PARTICLE PROPERTIES; PHASE TRANSFORMATIONS; PYRIDINES; SCATTERING; SPECTRA; STABLE ISOTOPES; SULFOXIDES; 400201* - Chemical & Physicochemical Properties; 360602 - Other Materials- Structure & Phase Studies; 640302 - Atomic, Molecular & Chemical Physics- Atomic & Molecular Properties & Theory

Citation Formats

Katrusiak, A, Kaluski, Z, Pietrzak, P, and Skolik, J. Molecular and crystal structure of bis-quinolizidine immonium salts, II:. delta. /sup 1(6)/-dehydrosparteinium monoperchlorate. United States: N. p., 1986. Web. doi:10.1007/BF01161107.
Katrusiak, A, Kaluski, Z, Pietrzak, P, & Skolik, J. Molecular and crystal structure of bis-quinolizidine immonium salts, II:. delta. /sup 1(6)/-dehydrosparteinium monoperchlorate. United States. doi:10.1007/BF01161107.
Katrusiak, A, Kaluski, Z, Pietrzak, P, and Skolik, J. Tue . "Molecular and crystal structure of bis-quinolizidine immonium salts, II:. delta. /sup 1(6)/-dehydrosparteinium monoperchlorate". United States. doi:10.1007/BF01161107.
@article{osti_6321396,
title = {Molecular and crystal structure of bis-quinolizidine immonium salts, II:. delta. /sup 1(6)/-dehydrosparteinium monoperchlorate},
author = {Katrusiak, A and Kaluski, Z and Pietrzak, P and Skolik, J},
abstractNote = {..delta../sup 1(6)/-Dehydrosparteinium monoperchlorate, (C/sub 15/H/sub 25/N/sub 2/)/sup +/ x ClO/sub 4//sup -/, is orthorhombic: P2/sub 1/2/sub 11/, a = 12.473(2), b = 24.292(3), c = 10.835(1) A, V/sub c/ = 3353.7(9) A/sup 3/, Z = 8, D/sub x/ = 1.32, D/sub m/ = 1.32 g cm/sup -3/, ..mu..(Cu K..cap alpha..) = 20.7 cm/sup -1/. The final R was 0.097 for 2091 observed counter reflections. A partial disorder of the crystal structure has been observed. The two independent perchlorate anions are orientationally disordered, and the peripheral atoms in the cation skeletons have large temperature factors due both to conformational disorder of rings A and to disordered orientations of the whole cations alike. In rings A, atoms C(3) and C(4), trans-annular to the immonium bond, are disordered to a different extent in each of the two independent cations. Rings B, C, and D have sofa (distorted towards half-chair), chair, and chair conformations, respectively. The quinolizidinium and quinolizidine moieties have planar and cis configurations, respectively. The title compound was obtained from ..delta../sup 5/-dehydrosparteine, the product of mercuric acetate dehydrogenation of sparteine at room temperature. From /sup 13/C NMR measurements in /sup 2/H/sub 2/O and in DMSO/sup 2/H/sub 6/ it is evident that, in solution, the molecular geometry with chair/chair cis-ring fusion within the quinolizidine moiety is present, as was in the crystalline state by X-ray analysis.},
doi = {10.1007/BF01161107},
journal = {J. Crystallogr. Spectrosc. Res.; (United States)},
number = ,
volume = 16:2,
place = {United States},
year = {1986},
month = {4}
}