Journal ArticleDOI
Recurrence of carboxylic acid-pyridine supramolecular synthon in the crystal structures of some pyrazinecarboxylic acids.
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TLDR
X-ray crystal structures of pyrazinic acid 1 and isomeric methylpyrazine carboxylic acids 2-4 are analyzed to examine the occurrence of car boxylic acid-pyridine supramolecular synthon V in these heterocyclic acids.Abstract:
X-ray crystal structures of pyrazinic acid 1 and isomeric methylpyrazine carboxylic acids 2-4 are analyzed to examine the occurrence of carboxylic acid-pyridine supramolecular synthon V in these heterocyclic acids. Synthon V, assembled by (carboxyl)O-H...N(pyridine) and (pyridine)C-H...O(carbonyl) hydrogen bonds, controls self-assembly in the crystal structures of pyridine and pyrazine monocarboxylic acids. The recurrence of acid-pyridine heterodimer V compared to the more common acid-acid homodimer I in the crystal structures of pyridine and pyrazine monocarboxylic acids is explained by energy computations in the RHF 6-31G* basis set. Both the O-H.N and the C-H...O hydrogen bonds in synthon V result from activated acidic donor and basic acceptor atoms in 1-4. Pyrazine 2,3- and 2,5-dicarboxylic acids 10 and 11 crystallize as dihydrates with a (carboxyl)O-H...O(water) hydrogen bond in synthon VII, a recurring pattern in the diacid structures. In summary, the carboxylic acid group forms an O-H...N hydrogen bond in pyrazine monocarboxylic acids and an O-H...O hydrogen bond in pyrazine dicarboxylic acids. This structural analysis correlates molecular features with supramolecular synthons in pyridine and pyrazine carboxylic acids for future crystal engineering strategies.read more
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Supramolecular synthesis of brick wall and honeycomb networks from the T-shaped molecule 5-nitrosalicylic acid
TL;DR: In this paper, the T-geometry of O−H⋯O and C−H−O hydrogen bonding groups in the title molecule (5-NSA) form a brick wall network that is modularly expanded and transformed to chair cyclohexane and honeycomb architectures in molecular complexes with trans-1,4-dithiane, 1,4dioxide and dioxane.
Journal ArticleDOI
Pyridinium boronic acid salts in crystal synthesis
TL;DR: A series of salts of pyridinium boronic acids: [HNC5H4B(OH)2-4]2[M(S2C2O2)2]·2H2O (M = Cu 1, Ni 2, Pd 3, Pt 4, Pt 5, Pt 6, Pt 7, Pt 8, Pt 9) have been prepared and characterized by X-ray diffraction methods as discussed by the authors.
Journal ArticleDOI
Interpenetration of distinct 2D and 3D organic networks in the crystal structure of 1,3,5-tris(4-methylbenzoyl)benzene
TL;DR: The triaroylbenzene derivative has a 2D hexagonal and a 3D α-polonium-type structure with two dimensionally distinct networks as discussed by the authors.
Journal ArticleDOI
Eight salts constructed from 4-phenylthiazol-2-amine and carboxylic acid derivatives through combination of strong hydrogen bonding and weak noncovalent interactions
TL;DR: The role of weak and strong non-covalent interactions in the crystal packing is ascertained in this paper, where eight crystalline organic salts derived from 4-phenylthiazol-2-amine and carboxylic acid derivatives were prepared and characterized by X-ray diffraction analysis, IR, mp, and elemental analysis.
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Infrared and ab initio studies on 1,2,4,5-tetrafluorobenzene clusters with methanol and 2,2,2-trifluoroethanol: presence and absence of an aromatic C-H...O hydrogen bond.
TL;DR: Both computational and experimental data indicate that an aromatic C-H...O hydrogen bond is present in theTFB-methanol cluster, while it is absent in the TFB-TFE cluster.
References
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Supramolecular Synthons in Crystal Engineering—A New Organic Synthesis
TL;DR: In this article, the authors show that crystal engineering is a new organic synthesis, and that rather than being only nominally relevant to organic chemistry, this subject is well within the mainstream, being surprisingly similar to traditional organic synthesis in concept.
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Noncovalent synthesis using hydrogen bonding
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Noncovalent Synthesis: Using Physical-Organic Chemistry To Make Aggregates
George M. Whitesides,Eric E. Simanek,John P. Mathias,Christopher T. Seto,Donovan N. Chin,Mathai Mammen,Dana M. Gordon +6 more
TL;DR: A molecule is usually understood to be a stable collection of atoms connected by a continuous network of covalent bonds as discussed by the authors, and the develipment of methods for constructing these networks has been a central occupation of organic chemistry, and the success of these methods has made possible the power, elegance and utility of modern organic synthesis.
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Photochemical reactions of organic crystals
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Superstructural diversity in two dimensions: crystal engineering of laminated solids
TL;DR: The application of self-assembly to the solid state offers an approach to crystal design and crystal engineering, namely supramolecular synthesis of solids, that is based upon the design of infinite networks.