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

Publikation: Beiträge in ZeitschriftenZeitschriftenaufsätzeForschungbegutachtet

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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 C 4n+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 C n-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. © 2013 Versita Warsaw and Springer-Verlag Wien.
OriginalspracheEnglisch
ZeitschriftCentral European Journal of Chemistry
Jahrgang11
Ausgabenummer9
Seiten (von - bis)1423-1430
Anzahl der Seiten8
ISSN1895-1066
DOIs
PublikationsstatusErschienen - 09.2013

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