Incorporation of steroidal biomarkers into petroleum model compounds
Scherer A, Hampel F, Gray M, Stryker J, Tykwinski R (2012)
Publication Type: Journal article, Original article
Publication year: 2012
Journal
Original Authors: Scherer A., Hampel F., Gray M., Stryker J., Tykwinski R.
Publisher: Wiley-Blackwell
Book Volume: 25
Pages Range: 597-606
Journal Issue: 7
DOI: 10.1002/poc.2931
Abstract
A series of fully-substituted 5,6-benzoquinolines covalently fused to the chlolestane framework has been synthesized to serve as model compounds for the poorly characterized components found in the heaviest fractions of petroleum, namely the asphaltenes. Acid-catalyzed cyclocondensation of an aromatic imine with 5-α-cholestan-3-one gives 5,6-benzoquinoline cycloadducts incorporating the steroidal biomarker fused to the benzoquinoline system at the 3,4-positions, with various pendent substituents in the 2-position. X-ray crystallography of three such derivatives shows that the solid-state geometries of these molecules are quite similar, and packing in the solid state appears to be dominated to a great extent by the nature of the pendent substituent. X-ray crystallography and solution phase circular dichroism spectroscopy together suggest that the conjugated benzoquinoline moiety adopts a helical conformation. Copyright © 2012 John Wiley & Sons, Ltd.
Authors with CRIS profile
Alexander Scherer
Lehrstuhl für Organische Chemie I
Frank Hampel
Lehrstuhl für Organische Chemie I
Rik Tykwinski
Lehrstuhl für Organische Chemie I
Involved external institutions
Canada (CA)How to cite
APA:
Scherer, A., Hampel, F., Gray, M., Stryker, J., & Tykwinski, R. (2012). Incorporation of steroidal biomarkers into petroleum model compounds. Journal of Physical Organic Chemistry, 25(7), 597-606. https://doi.org/10.1002/poc.2931
MLA:
Scherer, Alexander, et al. "Incorporation of steroidal biomarkers into petroleum model compounds." Journal of Physical Organic Chemistry 25.7 (2012): 597-606.
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