Graphical enumeration of hydrogen-bonded structures

Kuleshova, L. N.; Zorky, P. M.

doi:10.1107/s0567740880008047

Cited by 47 publications

(34 citation statements)

References 19 publications

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“…The resulting hydrogenbonding scheme resembles a honeycomb (see Fig. 2); according to Kuleshova & Zorky (1980) it can be classified as L](6) (not distinguishing C1 from N atoms for the sake of classification). A comparison of the N--CI distances in the title compound (Table 3) stronger in the former compound.…”

Section: In the Title Compound (Esd's In Parentheses)mentioning

confidence: 99%

Room-temperature phase of n-decylammonium chloride

Schenk¹,

Chapuis²

1986

Acta Crystallogr C

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Section: In the Title Compound (Esd's In Parentheses)mentioning

confidence: 99%

Room-temperature phase of n-decylammonium chloride

Schenk¹,

Chapuis²

1986

Acta Crystallogr C

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“…They identified finite sets, chains, layers and frameworks of hydrogen-bonded molecules, and they made initial surveys of the crystallographic literature to determine whether certain graph sets occurred more frequently than others. They also studied a set of hydrogen-bonded polymorphs and found that about half of them had the same graph set for both polymorphs (Zorky & Kuleshova, 1980). The graph-set method presented here uses a molecular version of graph-set representations of hydrogen-bond patterns where functional groups and molecular structure are used explicitly.…”

Section: Introductionmentioning

confidence: 99%

“…Hamilton & Ibers (1968) developed this idea further, characterizing hydrogen-bonded networks with two numbers (N, M), the number of hydrogen bonds per point (N), and the number of molecules to which a point is hydrogen bonded (M). Kuleshova & Zorky (1980) recognized that these early classification schemes were actually an application of graph theory, a mathematical formalism for analyzing graphs and networks (Harary, 1967). This theory has been used for many different chemical applications, such as analysis of stereochemical topology (Walba, 1987), development of synthetic strategies (Fujita, 1988a) and coding of reaction pathways (Fujita, 1988b).…”

Section: Introductionmentioning

confidence: 99%

Graph-set analysis of hydrogen-bond patterns in organic crystals

Etter¹,

MacDonald²,

Bernstein³

1990

Acta Crystallogr B Struct Sci

2,595

1,839

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The pressure-induced structural transformation of CHD involves, apart from other effects, the interchange of donor and acceptor sites by the enolic H atoms in the hydrogen bonds. The structure, despite its close similarities with antiferroelectric crystals, is ordered in the high-pressure phase, also retaining its low-pressure symmetry. It is possible that the crystals have a domain structure in both low-and highpressure phases. The proposed mechanism of the transformation strongly suggests an important role of electrostatic interactions in the transformation and in the jump of the enolic H atom to its other site in the OH---O bond. This mechanism also affords an explanation of the phase transition observed in CPD and of the exceptional stability of MCPD at high pressures; however, several points still need to be confirmed and further studies are being carried out on the CHD crystals.The author is grateful to Professor Z. Katuski for encouragement, to Dr R. J. Nelmes for his invitation to use the high-pressure and X-ray facilities of the Physics Department, University of Edinburgh, to Professor M. C. Etter of the Department of Chemistry, University of Minnesota, for stimulating discussions and providing the 1,3-cyclohexanedione samples crystallized from 2-pentanone, and to Dr J. Koput (Adam Mickiewicz University) for his expertise in the MNDO calculations. This study was partly supported by the British Council and by the Polish Academy of Sciences, Project CPBP, 01.12.References ALLMANN, R. (1977 AbstractA method is presented based on graph theory for categorizing hydrogen-bond motifs in such a way that complex hydrogen-bond patterns can be disentangled, or decoded, systematically and consistently. * Alfred P. Sloan Foundation Fellow, 1989-1991 This method is based on viewing hydrogen-bond patterns topologically as if they were intertwined nets with molecules as the nodes and hydrogen bonds as the lines. Surprisingly, very few parameters are needed to define the hydrogen-bond motifs comprising these networks. The methods for making these assignments, and examples of their chemical utility are given.

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“…The graph of Fig. 3 can be classified as F66(3,4,6) according to Kuleshova & Zorky (1980); F66 indicates that the graph has a three-dimensional framework, where each molecule is connected by 6 hydrogen bonds to 6 other molecules and (3,4,6) indicates the closed rings present in the graph. If the second component of the bifurcated hydrogen bond is also taken into account the symbol changes to F68(2,3,4,6) (each molecule forms 8 hydrogen bonds with 6 neighbors, closing rings of 2,3,4 and 6 elements).…”

Section: (5) C(ll)-o(l)mentioning

confidence: 99%