How to specify the structure of substituted blade-like zigzag diamondoids

• Authors: Alexandru Balaban , Christoph Rücker
• Languages of publication: EN

Abstracts

EN

Abstract The dualist of an [n]diamondoid consists of vertices situated in the centers of each of the n adamantane units, and of edges connecting vertices corresponding to units sharing a chair-shaped hexagon of carbon atoms. Since the polycyclic structure of diamondoids is rather complex, so is their nomenclature. For specifying chemical constitution or isomerism of all diamondoids the Balaban-Schleyer graph-theoretical approach based on dualists has been generally adopted. However, when one needs to indicate the location of C and H atoms or of a substituent in a diamondoid or the stereochemical relationships between substituents, only the IUPAC polycycle nomenclature (von Baeyer nomenclature) provides the unique solution. This is so since each IUPAC name is associated with a unique atom numbering scheme. Diamondoids are classified into catamantanes (which can be regular or irregular), perimantanes, and coronamantanes. Regular catamantanes have molecular formulas C4n+6H4n+12. Among regular catamantanes, the rigid blade-shaped zigzag catamantanes (so called because their dualists consist of a zigzag line with a code of alternating digits 1 and 2) exhibit a simple pattern in their von Baeyer nomenclature. Their carbon atoms form a main ring with 4n + 4 atoms, and the remaining atoms form two 1-carbon bridges. All zigzag [n]catamantanes with n > 2 have quaternary carbon atoms, and the first bridgehead in the main ring is such an atom. Their partitioned formula is Cn−2(CH)2n+4(CH2)n+4. As a function of their parity, IUPAC names based on the von Baeyer approach have been devised for all zigzag catamantanes, allowing the unique location for every C and H atom. The dualist of such a zigzag catamantane defines a plane bisecting the molecule, and the stereochemical features of hydrogens attached to secondary carbon atoms can be specified relatively to that plane. Graphical abstract [...]

Keywords

EN

Diamondoids; Dualists; Catamantanes; IUPAC nomenclature

• Publisher: De Gruyter Open
• Journal: Open Chemistry
• Year: 2013
• Volume: 11
• Issue: 9
• Pages: 1423-1430

Dates

published

1 - 9 - 2013

online

29 - 6 - 2013

Contributors

author

Alexandru Balaban

• Texas A&M University at Galveston, Galveston, TX, 77553, USA

author

Christoph Rücker

• Leuphana University Lüneburg, D-21335, Lüneburg, Germany

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Identifiers

DOI

10.2478/s11532-013-0275-7