Hydrogen bonding <i>vs.</i> stacking interaction in the crystals of the simplest coumarin derivatives: a study from the energetic viewpoint

Shishkina, Svitlana V.; Konovalova, Irina S.; Kovalenko, Sergiy M.; Trostianko, Pavlo V.; Geleverya, Anna O.; Bunyatyan, N. D.

doi:10.1039/c9ce01344j

Cited by 9 publications

(5 citation statements)

References 44 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…This gave 18 hits with a considerable spread of C N-C angles, namely 120.5-127.9 , mean value 123.4 (24) . Nine of these structures appeared in the same publication (Shishkina et al, 2019), and, like 7, none of them had an interplanar angle close to the calculated gas-phase optimum of 0 . Yellow crystals (seen under the microscope to be orange/ yellow dichroic); yield: 94% (4.21 g); m.p.…”

Section: Database Surveymentioning

confidence: 72%

Crystal structure of N-[3-(benzo[d]thiazol-2-yl)-6-bromo-2H-chromen-2-ylidene]-4-methylbenzenamine

2023

View full text Add to dashboard Cite

The title compound, C23H15BrN2OS, was the unexpected product in an attempted synthesis of the isomeric 3-(benzo[d]thiazol-2-yl)-6-bromo-1-p-tolylquinolin-2(1H)-one. The Cchromene=N—C angle is wide [125.28 (8)°]. The benzothiazole and chromene ring systems are almost coplanar, with their planes parallel to (1\overline{1}0); the toluene ring system is rotated by ca 40° out of the chromene plane. The molecular packing involves layers with π-stacking, borderline `weak' hydrogen bonds and possible C—H...π contacts.

show abstract

Section: Database Surveymentioning

confidence: 72%

Crystal structure of N-[3-(benzo[d]thiazol-2-yl)-6-bromo-2H-chromen-2-ylidene]-4-methylbenzenamine

2023

View full text Add to dashboard Cite

show abstract

“…These interactions are well within the range prescribed for a coumarin containing heterocyclic systems reported elsewhere. [ 21 ] Finally, all short‐range interactions along with hydrogen bonding, CH‐‐‐‐Ni anagostic‐type and π–π stacking interactions led to the formation of a three‐dimensional network among the complex molecules.…”

Section: Resultsmentioning

confidence: 99%

Glucose electrocatalysts derived from mono‐ or dicarbene coordinated nickel(II) complexes and their mesoporous carbon composites

Yhobu

Brinda

Achar

et al. 2021

Applied Organom Chemis

View full text Add to dashboard Cite

Molecular electrocatalysts that contain a metal atom under precise ligand field in a definite geometry feasible for redox reactions has boundless significance in numerous electrocatalytic reactions. Herein, we report nickel‐based molecular electrocatalysts anchored on the sterically varied 1,2,4‐triazol‐5‐ylidene ligands. The two metal complexes bearing different ligand system wherein one is mono‐NHC nickel(II) complex and the other is a bis‐NHC nickel(II) complex were compared and studied in terms of morphology and electrochemical glucose sensing. The kinetics and sensitivity of the nickel(II) complexes were significantly enhanced by the mesoporous carbon and demonstrated high electrode sensitivity (2.57–124.92 μA mM−1 cm−2) at a fixed potential towards glucose detection. The chronoamperometric studies evidenced the detection of glucose up to 27.5 mM with a linear range of detection up to 9.5 mM (LOD of 44.59 μM). The selectivity towards glucose in the presence of other blood constituents was investigated. Finally, the stability was studied after 18 days of electrode preparation, and negligible variation in the glucose sensing performance was found. The electrocatalysts prepared are found to be the viable candidates for potential engineering high‐performance molecular non‐enzymatic glucose sensor.

show abstract

“…Monoclinic crystals of 1m were obtained after 1-2 days from the acetonitrile and acetone solutions. The structure of 1m crystallized from the acetonitrile solution was studied earlier (Shishkina et al, 2019) and deposited with the Cambridge Crystallographic Data Centre and assigned refcode TOSFAL.…”

Section: Crystallizationmentioning

confidence: 99%

“…Four new polymorphic modifications of this very simple compound have been obtained from the melt and their structures were proved using a combination of crystal prediction and powder diffraction methods (Shtukenberg et al, 2017). We have synthesized the carboxamide and thiocarboxamide derivatives of coumarin (Scheme I left-hand side) and 2-iminocoumarin and studied their crystal structures (Shishkina et al, 2019). Surprisingly, the crystals of coumarin-3-carboxamide and 2-iminocoumarin-3-carboxamide proved to be isostructural despite the opposite role of the carbonyl and imino groups in the formation of intermolecular interactions.…”

Section: Introductionmentioning

confidence: 99%

Concomitant polymorphs of 2-imino-2H-chromene-3-carboxylic acid amide: experimental and quantum chemical study

Shishkina,

Shaposhnyk,

Konovalova

et al. 2024

Acta Crystallogr Sect B

Self Cite

View full text Add to dashboard Cite

2-Iminocoumarin-3-carboxamide (2-imino-2 H-chromene-3-carboxylic acid) is a perspective compound for use in the pharmaceutical industry. This compound crystallized from several solvents as two concomitant polymorphic forms. The monoclinic polymorph, crystallized initially, is formed due to strong N—H...O hydrogen bonds, weak C—H...O and C—H...N(π) hydrogen bonds, and stacking interactions of `head-to-head' type. The triclinic polymorphic form obtained due to slow evaporation of the same solution is formed due to only strong intermolecular interactions, N—H...O hydrogen bonds of two types, and stacking interactions of two types. Analysis of pairwise interaction energies showed that the monoclinic structure is columnar while the triclinic one is layered. Calculations in a periodic approximation of their lattice energies confirmed that the monoclinic polymorphic crystals are metastable as compared to the stable triclinic polymorph. Further quantum chemical modeling of possible structure deformations proved that both concomitant polymorphs can not be transformed into a new polymorphic form under external influence.

show abstract

Hydrogen bonding vs. stacking interaction in the crystals of the simplest coumarin derivatives: a study from the energetic viewpoint

Abstract: Hydrogen bonded and stacked dimers have very close interaction energies in the crystals of the simplest coumarin derivatives according to the data of the crystal structure analysis based on the comparison of pairwise interaction energies.

Cited by 9 publications

References 44 publications

Crystal structure of N-[3-(benzo[d]thiazol-2-yl)-6-bromo-2H-chromen-2-ylidene]-4-methylbenzenamine

Crystal structure of N-[3-(benzo[d]thiazol-2-yl)-6-bromo-2H-chromen-2-ylidene]-4-methylbenzenamine

Glucose electrocatalysts derived from mono‐ or dicarbene coordinated nickel(II) complexes and their mesoporous carbon composites

Concomitant polymorphs of 2-imino-2H-chromene-3-carboxylic acid amide: experimental and quantum chemical study

Contact Info

Product

Resources

About