Journal ArticleDOI
Distinguishment of Weak Interactions of Hydrogen Atoms Bound to Carbon Atoms: X-Ray Crystal Structural and Hirshfeld Surface Analyses of 2- Hydroxy-7-methoxy-3-(2,4,6-trimethylbenzoyl)naphthalene with the 2- Methoxylated Homologue
Toyokazu Muto,Kikuko Iida +1 more
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In this paper , X-ray crystal and Hirshfeld surface analyses of 2-hydroxy-7methoxy-3-(2,4,6- trimethylbenzoyl)naphthalene and its 2-methoxylated homologue were performed.Abstract:
Abstract: X-ray crystal and Hirshfeld surface analyses of 2-hydroxy-7-methoxy-3-(2,4,6- trimethylbenzoyl)naphthalene and its 2-methoxylated homologue show quantitatively and visually distinct molecular contacts in crystals and minute differences in the weak intermolecular interactions. The title compound has a helical tubular packing, where molecules are piled in a two-folded head-to-tail fashion. The homologue has a tight zigzag molecular string lined up behind each other via nonclassical intermolecular hydrogen bonds between the carbonyl oxygen atom and the hydrogen atom of the naphthalene ring. The dnorm index obtained from the Hirshfeld surface analysis quantitatively demonstrates stronger molecular contacts in the homologue, an ethereal compound, than in the title compound, an alcohol, which is consistent with the higher melting temperature of the former than the latter. Stabilization through the significantly weak intermolecular nonclassical hydrogen bonding interactions in the homologue surpasses the stability imparted by the intramolecular C=O…H–O classical hydrogen bonds in the title compound. The classical hydrogen bond places the six-membered ring in the concave of the title molecule. The hydroxy group opposingly disturbs the molecular aggregation of the title compound, as demonstrated by the distorted H…H interactions covering the molecular surface, owing to the rigid molecular conformation. The position of effective interactions predominate over the strength of the classical/nonclassical hydrogen bonds in the two compounds. read more
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Journal ArticleDOI
Weak Interaction Based Interpretation of Crystal Packing Characteristics of Aromatic Rings Accumulating Molecules: Hirshfeld Surface Analyses Reinforced X-ray Crystal Study on 1,8-Dibenzoyl-7-Ethoxynaphthalen-2-ol and Its 2-Ethoxylated Homologue
Posted ContentDOI
Weak interaction based interpretation of crystal packing characteristics of aromatic rings accumulating molecules: Hirshfeld surface analyses reinforced X-ray crystal study on 1,8-dibenzoyl-7-ethoxynaphthalen-2- ol and its 2-ethoxylated homologue
TL;DR: In this paper , the molecular vicinity characteristics in the crystal of two dibenzoylnaphthalene derivatives having intimately similar molecular formula with solely one substituent difference, 2-hydroxy group or 2-ethoxy one, were comparatively investigated in relation to the types of weak interactions with the aid of X-ray crystal structural study reinforced by Hirshfeld surface analyses and two-dimensional plotting of the normalised interatomic distance crossing the molecular surface.
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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Characterization of c-h-o hydrogen-bonds on the basis of the charge-density
Uwe Koch,Paul L. A. Popelier +1 more
TL;DR: In this paper, a set of criteria are proposed based on the theory of "atoms in molecules" to establish hydrogen bonding, even for multiple interactions involving C-H-O hydrogen bonds.