Systematic classification and nomenclature of diamond hydrocarbons—I

Balaban, Alexandrù T.; Schleyer, P. Von R.

doi:10.1016/0040-4020(78)88437-3

Cited by 101 publications

(101 citation statements)

References 45 publications

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“…As discussed earlier without enetering into detail, 17 adamantane units may also share single carbon atoms yielding spiromantanes, one or two C-C bonds (oneedge-or two-edge-mantanes). All these possibilities have been and exemplified, paying special attention to macrocyclic assemblies of adamantane units.…”

Section: Discussionmentioning

confidence: 99%

“…15,16 For specifying constitutional structures of diamondoids, Balaban and Schleyer conceived a similar system that is also based on their dualists. 17 In this case, the 3D diamond lattice is self-dual. A diamondoid formed from n adamantane units with an acyclic dualist is called an [n]catamantane, but catamantanes are of two kinds: regular catamantanes when the molecular formula is C 4n+6 H 4n+12 and irregular ones when there are fewer C and H atoms for a given n value.…”

Section: Introductionmentioning

confidence: 99%

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Cyclic Diamondoid Structures with Shared Vertices, Edges, or 6-membered Rings

Balaban¹

2015

Croat. Chem. Acta

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Abstract. Diamondoid structures with shared vertices, edges, or 6-membered rings can theoretically be curved into toroidal structures whose calculated energy provides information about steric strain. Diamondoid hydrocarbons sharing one vertex between two adamantane units are called [n]spiromantanes, where n indicates the number of adamantane units. When a pair of adamantane units shares one CC bond, the resulting assembly is called one-edge-[n]mantane, specifying (by letters in square brackets) which bonds are shared by the adamantane units. Two adjacent edges may be shared by a pair of adamantane units, and the assembly is called two-edge-[n]mantane, again specifying by letters in square brackets the shared bonds. Catamantanes or perimantanes sharing a 6-membered ring of carbon atoms may form larger rings in an assembly which is called [n]cyclomantane; in the case of catamantanes, the structure of the diamondoid is specified by codes of the dualists. Finally, nanotubes derived from hexagonal diamond, as well as corresponding toroidal structures, are discussed.

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Cyclic Diamondoid Structures with Shared Vertices, Edges, or 6-membered Rings

Balaban¹

2015

Croat. Chem. Acta

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“…The code for diamondoid isomers (introduced by Balaban and Schleyer) is a succession of digits 1, 2, 3, or 4 for the directions of CC bonds around tetrahedral C atoms, between two ends of the molecule. 21 When going from a planar benzenoid to a three-dimensional diamondoid, one has to take chirality into account:…”

Section: Coronamantanes Having Holes Completely Encased By Adamantanementioning

confidence: 99%

Theoretical Study of Hole-Containing Macromolecular Diamond Lattices and Corona-Diamondoid Molecules or their Heteroatomic Derivatives

Balaban¹

2013

Croat. Chem. Acta

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Abstract. By analogy with benzenoids, diamond hydrocarbons (diamondoids for short) can be classified according to their dualists into catamantanes with acyclic dualists, perimantanes with dualists having 6-membered rings, and coronamantanes having larger rings that are not peripheries of 6-membered ring aggregates. Coronoid diamond hydrocarbons may be either tridimensional portions of the macromolecular diamond lattice with holes examined in an earlier article and here, or hollow smaller molecules (coronamantanes) also discussed in the present paper, with 3D or quasi-2D holes. In the case of lattices, the effect of external hydrogen atoms is negligible but it cannot be ignored in the case of coronamantanes. Both the outer and inner dangling bonds may be connected with hydrogen atoms, or some of the inner carbon atoms with dangling bonds may be replaced by heteroatoms (N, O, or S) which might be able to bind metallic cations with coordinative bonds. A convenient means of structure representation uses dualists of the diamondoids. The holes may be isolated as are "closed pores" in polymer foams, or they may communicate forming tunnels as for 'open pores' in 'sponge foams'. A special discussion is reserved for coronamantane analogs of the quasi-planar coronoids. In these cases the diamondoid is quasi-flat and the quasi-2D hole or tunnel is accessible on both sides; it may be chiral or achiral. The diamondoid analog of kekulene is a cyclohexadecamantane C 64 H 64 , a challenge for the future. (doi: 10.5562/cca2288)

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“…According to this analogy, the structures of diamondoid and benzenoid hydrocarbons are characterized by their dualists, consisting of vertices in the centers of the constituent units and of edges connecting vertices corresponding to adjacent units. 3,4 Whereas the dualist of the graphene lattice is a triangular lattice (and vice-versa), the diamond lattice is self-dual, i. e. the dualist of the diamond lattice is itself a diamond lattice. As a side remark, the 2D square lattice and the 3D cubic net are also self-dual.…”

Section: Introductionmentioning

confidence: 99%

“…Biologically active derivatives of diamondoids offer hopes for drug design based on the hydrophobicity and antiviral properties of diamondoid derivatives such as adamantylamine. For various diamondoid structures, Balaban and Schleyer 3 proposed a naming and coding system based on the four directions around an sp 3 -hybridized carbon atom and encoded by digits 1, 2, 3, and 4 according to a simple procedure. This system is generally accepted at present.…”

Section: Introductionmentioning

confidence: 99%

Helical [n]catamantanes and all-trans-perhydroacenic [n]perimantanes: structures and von Baeyer IUPAC numbering of carbon atoms

Balaban¹,

Rücker²

2013

Arkivoc

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Abstract[n]Diamondoids are hydrocarbons whose carbon skeleton is a portion of the diamond lattice, and contains n adamantane cells (or units) sharing chair-shaped hexagons of carbon atoms. When centers of these adamantane units are connected by lines, the resulting construction is called the dualist of the diamondoid, and it also is similar to a portion of the diamond lattice. While these hydrocarbons can be distinguished by the Balaban-Schleyer nomenclature system, substituted derivatives are to be described by the IUPAC von Baeyer nomenclature that attributes a unique number (locant) to each carbon atom within a molecule. In this paper, von Baeyer names and corresponding atom numberings were obtained by the computer program POLCYC for members of two classes of diamondoids: [n]catamantanes whose dualists are tight helices, and [n]perimantanes whose dualists are all-trans-perhydroacenes; general numbering schemes were derived for these compound classes. The structures and some regularities in their structural properties are discussed.

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Systematic classification and nomenclature of diamond hydrocarbons—I

Cited by 101 publications

References 45 publications

Cyclic Diamondoid Structures with Shared Vertices, Edges, or 6-membered Rings

Cyclic Diamondoid Structures with Shared Vertices, Edges, or 6-membered Rings

Theoretical Study of Hole-Containing Macromolecular Diamond Lattices and Corona-Diamondoid Molecules or their Heteroatomic Derivatives

Helical [n]catamantanes and all-trans-perhydroacenic [n]perimantanes: structures and von Baeyer IUPAC numbering of carbon atoms

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