Centrohexacyclic or “<i>K</i><sub>5</sub>” Molecules: Development of a Growing Family of Topologically Nonplanar Organic Compounds

Kuck, Dietmar

doi:10.1002/jlac.199719970603

Cited by 28 publications

(17 citation statements)

References 68 publications

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“…as early as 1983 [191,192]. Over the years, various graph theoretical aspects of K 5 ‐ and K 3,3 ‐hydrocarbons and ‐polyethers[193] have been discussed in several reviews [194–197]…”

Section: The Centrohexaindane Storymentioning

confidence: 99%

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

Kuck

2015

The Chemical Record

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Detailed insights gained from our research into the gas-phase chemistry of ionized and protonated diphenylalkanes and their congeners, obtained by extended synthesis of isotopically labeled model compounds and mass spectrometry, are presented and merged with those acquired during our development of a new family of polycyclic hydrocarbons, the centropolyindanes. Aside from a Personal Account that describes "two scientific lives in one", it is demonstrated, on the one hand, how our understanding of organic chemistry can help to shed light on the details of mass spectrometric fragmentation and to unravel, in a more fundamental way, the unimolecular reactivity of gaseous ions. On the other hand, it is shown how unexpected reactivity of related ions in solution, being subject to the very same fundamentals of organic chemistry, can lead to the construction of novel and, in part, unique three-dimensional polycyclic structures that may contribute to future research in material science. Two such apparently independent fields of organic chemistry may be seen as joint contributions of the art of science.

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Section: The Centrohexaindane Storymentioning

confidence: 99%

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

Kuck

2015

The Chemical Record

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“…If G is planar , a minimum cycle basis can be found in time

O (m^{2} + n \log n)

, . Note, however, that there are nonplanar molecules (e.g., Kuratowskiphane , see ). See for a survey on structural and algorithmic results on cycle bases and other applications.…”

Section: Preliminariesmentioning

confidence: 99%

Computing cyclic invariants for molecular graphs

2017

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Ring structures in molecules belong to the most important substructures for many applications in Computational Chemistry. One typical task is to find an implicit description of the ring structure of a molecule. We present efficient algorithms for cyclic graph invariants that may serve as molecular descriptors to accelerate database searches. Another task is to construct a well‐defined set of rings of a molecular graph explicitly. We give a new algorithm for computing the set of relevant cycles of a graph. © 2017 Wiley Periodicals, Inc. NETWORKS, Vol. 70(2), 116–131 2017

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“…Three spectacular examples are given in Figures 6 and 10, other examples are described e.g. in [2,37,44,47,53]. Figure 6.…”

Section: Minimum Planar Cycle Basesmentioning

confidence: 99%

Counterexamples in Chemical Ring Perception

Berger

Flamm

Gleiss

et al. 2004

J. Chem. Inf. Comput. Sci.

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Abstract. Ring information is a large part of the structural topology used to identify and characterize molecular structures. It is hence of crucial importance to obtain this information for a variety of tasks in computational chemistry. Many different approaches for "ring perception", i.e., the extraction of cycles from a molecular graph, have been described. The chemistry literature on this topic, however, reports a surprisingly large number of incorrect statements about the properties of chemically relevant ring sets and, in particular, about the mutual relationships of different sets of cycles in a graph. In part these problems seem to have arisen from a sometimes rather idiosyncratic terminology for notions that are fairly standard in graph theory. In this contribution we translate the definitions of concepts such as the Smallest Set of Smallest Rings, Essential Set of Essential Rings, Extended Set of Smallest Rings, Set of Smallest Cycles at Edges, Set of Elementary Rings, K-rings, and β-rings into a more widely-used mathematical language. We then outline the basic properties of different cycle sets and provide numerous counterexamples to incorrect claims in the published literature. These counterexamples may have a serious practical impact because at least some of them are molecular graphs of well-known molecules. As a consequence, we propose a catalogue of desirable properties for chemically useful sets of rings.

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Centrohexacyclic or “K₅” Molecules: Development of a Growing Family of Topologically Nonplanar Organic Compounds

Cited by 28 publications

References 68 publications

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

Computing cyclic invariants for molecular graphs

Counterexamples in Chemical Ring Perception

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Centrohexacyclic or “K5” Molecules: Development of a Growing Family of Topologically Nonplanar Organic Compounds

Cited by 28 publications

References 68 publications

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

From Fragmentation to Construction—from Void to Massive: Fascination with Organic Mass Spectrometry and the Synthesis of Novel Three‐Dimensional Polycyclic Aromatic Hydrocarbons

Computing cyclic invariants for molecular graphs

Counterexamples in Chemical Ring Perception

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Centrohexacyclic or “K₅” Molecules: Development of a Growing Family of Topologically Nonplanar Organic Compounds