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
Citations
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Journal ArticleDOI
Heteromeric intermolecular interactions as synthetic tools for the formation of binary co-crystals
TL;DR: The crystal structure of 4-nitrobenzamide pyrazinecarboxamide (1 ∆∆ 1) contains two homomeric amide-amide dimers, which is in contrast with the structural motifs displayed by the vast majority of binary co-crystals as discussed by the authors.
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Coformer selection based on degradation pathway of drugs: a case study of adefovir dipivoxil-saccharin and adefovir dipivoxil-nicotinamide cocrystals.
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Controlling molecular and supramolecular structure of hydrogen-bonded coordination compounds
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References
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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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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.