Quantitative Insights into the Crystal Structures of Nitro Derivatives of Ethyl (2E)-2-cyano-3-phenylprop-2-enoate: Inputs from X-Ray Diffraction, DFT Calculations and Hirshfeld Surface Analysis

Dey, Dhananjay; Prakash, V.; Chopra, Deepak; Vasu,; Srinivas, Madnimaraiah

doi:10.1007/s10870-014-0536-0

Cited by 3 publications

(2 citation statements)

References 21 publications

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“…This fact explains the high energy values found for the halogen bonds, and C-H⋯OĲN), C-H⋯π and π⋯π (2-8 kcal mol −1 ) interactions in some crystal dimers described in the literature. [19][20][21][22] On the contrary, by partitioning the dimer interaction energy into specific atom⋯atom interactions, it is possible to estimate a reasonable value for the energies of intermolecular atom⋯atom interactions. The energy of each intermolecular interaction present in each dimer of compounds 1-3 was determined, and is expressed as G AI in Table 2.…”

Section: Resultsmentioning

confidence: 99%

Proposal for crystallization of 3-amino-4-halo-5-methylisoxazoles: an energetic and topological approach

et al. 2015

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a The supramolecular structure of 3-amino-4-halo-5-methylisoxazoles (with halo = Cl, Br, I) was investigated in order to suggest a route for crystallization of small molecules. The hierarchy of intermolecular interactions during the growth of the crystal was established by x-ray diffraction, 1 H NMR titration, QTAIM analysis and quantum mechanical calculations. The relationship between QTAIM and energetic data was the fundamental innovation in this work. It allowed the partitioning of the dimer interaction energy between interacting atoms. Partitioning shows the cooperation of intermolecular interactions in the stabilization of dimers and led to observation of the energetic consequences that small changes in the molecular structure of each compound may have on the crystal packing. The proposed route for crystallization of the supramolecular cluster was based on the energetic hierarchy, in which the hydrogen bond is the strongest interaction and the first to form, and the π-interactions are weaker than the hydrogen bond and cannot compete with it. However, the πinteractions are responsible for the growth of the crystal connecting the rising layers of the hydrogen bond dimers. The other interaction formed, the halogen bond, is too weak to compete with the other two interactions, but it is fundamental for linking the layer that leads to the final three-dimensional arrangement. Finally, a new way of understanding the crystallization process and the design of new materials is presented. 11-13Our objective herein is to further our study of the analysis of the crystal packing of heterocycles, taking into account consequences arising from small changes in molecular

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Section: Resultsmentioning

confidence: 99%

Proposal for crystallization of 3-amino-4-halo-5-methylisoxazoles: an energetic and topological approach

et al. 2015

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“…The study of intermolecular interactions has become prominent in crystal structure analyses in the last decade [17][18][19][20][21][22][23][24]. Hirshfeld surface analysis is a characteristic method to visualize and characterize the intermolecular interactions of molecular crystals.…”

Section: Single-crystal X-ray Structuresmentioning

confidence: 99%

Physicochemical characterization and decomposition kinetics of (S)-4-[1-(2,3-dimethylphenyl)ethyl]-3H-imidazole HCl/S-enantiomer of medetomidineHCl

Pansuriya

Maguire

Friedrich

2015

J Therm Anal Calorim

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Physicochemical characterization of (S)-4-[1-(2,3-dimethylphenyl)ethyl]-3H-imidazole HCl in solution as well as the solid state has been done using single-crystal X-ray crystallography, 1 H and 13 C NMR, IR and mass spectrometry. The single-crystal structure, as well as Hirshfeld surface analysis, of the S-enantiomer is compared with the racemate, as well as the polymorph of the racemate. The decomposition kinetics of the S-enantiomer have been studied using thermogravimetric analysis and a differential scanning calorimetric investigation. The study was done to contribute to understanding the properties of the drug at a molecular level, thus providing tools to develop novel formulations of the drug.

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Synthesis of (E)-α,β-unsaturated carboxylic esters derivatives from cyanoacetic acid via promiscuous enzyme-promoted cascade esterification/Knoevenagel reaction

Wilk

Trzepizur

Koszelewski

et al. 2019

Bioorganic Chemistry

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Quantitative Insights into the Crystal Structures of Nitro Derivatives of Ethyl (2E)-2-cyano-3-phenylprop-2-enoate: Inputs from X-Ray Diffraction, DFT Calculations and Hirshfeld Surface Analysis

Cited by 3 publications

References 21 publications

Proposal for crystallization of 3-amino-4-halo-5-methylisoxazoles: an energetic and topological approach

Proposal for crystallization of 3-amino-4-halo-5-methylisoxazoles: an energetic and topological approach

Physicochemical characterization and decomposition kinetics of (S)-4-[1-(2,3-dimethylphenyl)ethyl]-3H-imidazole HCl/S-enantiomer of medetomidineHCl

Synthesis of (E)-α,β-unsaturated carboxylic esters derivatives from cyanoacetic acid via promiscuous enzyme-promoted cascade esterification/Knoevenagel reaction

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