Isolation and Structural Proof of the Large Diamond Molecule, Cyclohexamantane (C<sub>26</sub>H<sub>30</sub>)

Dahl, Jeremy E. P.; Moldowan, J. Michael; Peakman, Torren M.; Clardy, Jon; Lobkovsky, Emil; Olmstead, Marilyn M.; May, Paul; Davis, Timothy J.; Steeds, John W; Peters, K. E.; Pepper, Andy; Ekuan, Andy; Carlson, Robert M. K.

doi:10.1002/ange.200250794

Cited by 40 publications

(44 citation statements)

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“…Functionalized diamondoids obtained by regioselective reactions offer a wide range of possible shapes in three dimensions. [14][15][16]21,22 In order to specify the location and stereochemistry of substituents, the von Baeyer nomenclature enhanced by stereochemical descriptors as advocated here is the best available system.…”

Section: Stereochemical Aspects In Perimantanes That Have As Dualistsmentioning

confidence: 99%

“…7, top). 15 15 This name, however, though correctly describing the structure, was not correct in the sense of IUPAC rule VB-6-4, which states "The superscript locants of the secondary bridges shall be as small as possible when considered as a set in ascending numerical order, a decision being made at the first point of difference". 8 In 2009 a different numbering scheme for cyclohexamantane was used, 16 The second member of this class has as dualist the graph corresponding to trans-decalin, see Figure 7, second structure.…”

Section: Introductionmentioning

confidence: 99%

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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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Section: Stereochemical Aspects In Perimantanes That Have As Dualistsmentioning

confidence: 99%

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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“…While higher diamondoids that are composed of more than four units were first isolated from crude oil [11,12], the availability of diamondoids above the 2nd member, diamantane, is limited. Many attempts have been undertaken to obtain diamondoids synthetically, but with the exception of triamantane [13] and anti-tetramantane [14], no other diamondoids have been obtained by conventional organic synthesis.…”

Section: Introductionmentioning

confidence: 99%

Reaction yields of diamondoid synthesis by plasmas generated in supercritical xenon

Stauss

Shizuno

Miyazoe

et al. 2013

Trans. Mat. Res. Soc. Japan

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Diamondoids are sp3 -hybridized carbon nanomaterials that hold promise for application in biotechnology, medicine, and opto-and nanoelectronics. While difficult or even impossible to realize by conventional organic synthesis methods, the synthesis of larger diamondoids was demonstrated by plasmas generated in supercritical fluids, however, the reaction mechanisms that lead to their formation are not clear. Here, we investigated the synthesis of diamondoids from adamantane and present a simple model that predicts the reaction rates of diamantane, triamantane, and tetramantane. The diamondoids were synthesized by micro dielectric barrier discharges arranged in arrays, generated at frequencies of 7 kHz and applied voltages of 5 − 10 kV p−p in supercritical xenon (pressure 5.56 − 8.22 MPa, temperature 290.0 − 310.2 K). The collected samples were analyzed and quantified by gas chromatography -mass spectrometry measurements. The reaction yields of diamantane increase with increasing precursor density and longer reaction times. Experimental data also suggests a stepwise reaction of higher diamondoids from lower diamondoids, and predicts lower reaction rates for higher diamondoids when compared to lower diamondoids.

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“…Individual diamondoids with many potential applications (such as antiviral compounds, field emitters, components of molecular motors, nanorods as spacers in pharmaceuticals), being the most stable among their isomers, can be isolated via thermal treatments. Diamondoids are more thermally stable than nondiamondoid hydrocarbons (e.g., acyclic hydrocarbons) in petroleum systems, and therefore become concentrated in the natural gas condensates as they form over geologic time [3].Thermal treatments are similarly used to produce fractions extremely rich in diamondoids [1,2]. Moreover, diamondoids are more stable than graphite in the sub-5 nm size range (contrary to the stability relationship of macroscopic diamond and graphite).…”

Section: Introductionmentioning

confidence: 99%

“…The surprising discovery and isolation of higher diamondoids (or polymantanes, hydrocarbons whose carbon scaffold is part of the diamond lattice) was recently reported [1,2]. Consequently one desires theoretical methods for correlating structures with properties for these unique and useful compounds, only available from petroleum [3].…”

Section: Introductionmentioning

confidence: 99%

Molecular Descriptors for Natural Diamondoid Hydrocarbons and Quantitative Structure-Property Relationships for Their Chromatographic Data

Balaban¹,

Klein²,

Dahl³

et al. 2007

TOOCJ

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Diamond hydrocarbons (or diamondoids) are hydrocarbons that have a carbon skeleton superimposable on the diamond lattice and contain one or more adamantane units. Recently it was found that many higher diamondoids (containing four to eleven adamantane units) are present in petroleum and can be isolated by a series of methods that include HPLC and GC techniques. We develop QSPR equations using molecular descriptors derived from the topology and geometry of diamondoids, by means of dualist graphs consisting of vertices placed at the centers of adamantane cells forming the diamondoid, and of edges connecting vertices centered in adamantane cells sharing faces. From distance (or distancedistance) matrices encoding the topology and geometry of diamondoids one can obtain distance-sums, distance-distance sums, or eigenvectors as molecular descriptors characterizing the diamondoids. These descriptors afford satisfactory correlations with GC and HPLC retention data, and may also facilitate the identification of diamondoid isomers.

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Isolation and Structural Proof of the Large Diamond Molecule, Cyclohexamantane (C₂₆H₃₀)

Cited by 40 publications

References 20 publications

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

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

Reaction yields of diamondoid synthesis by plasmas generated in supercritical xenon

Molecular Descriptors for Natural Diamondoid Hydrocarbons and Quantitative Structure-Property Relationships for Their Chromatographic Data

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Isolation and Structural Proof of the Large Diamond Molecule, Cyclohexamantane (C26H30)

Cited by 40 publications

References 20 publications

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

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

Reaction yields of diamondoid synthesis by plasmas generated in supercritical xenon

Molecular Descriptors for Natural Diamondoid Hydrocarbons and Quantitative Structure-Property Relationships for Their Chromatographic Data

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Product

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Isolation and Structural Proof of the Large Diamond Molecule, Cyclohexamantane (C₂₆H₃₀)