Cocrystallization of 2,3-dimethylquinoxaline with 3,5-dinitrobenzoic acid: Crystal structure, Hirshfeld surface, spectroscopic features and DFT studies

Faizan, Mohd; Rodrigues, V. H.; Ahmad, Shabbir

doi:10.1016/j.molstruc.2019.126894

Cited by 17 publications

(2 citation statements)

References 55 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…MEPs reveals the electrophilic and nucleophilic positions of molecules and is an extremely effective and widely accepted quantum-molecular descriptor for calculating the most important reactive sites. − MEPs descriptor indicates the sensitivity of molecule toward the interactions with other molecules based on the electrostatic interactions and is carried out to predict the contact of cocrystals. , The best donor and the best acceptor of a hydrogen bond will preferably form hydrogen bonds with one another …”

Section: Resultsmentioning

confidence: 99%

Enhancing Stability and Formulation Capability of Fungicides by Cocrystallization through a Novel Multistep Slurry Conversion Process

Jin

Gong

et al. 2020

Crystal Growth & Design

View full text Add to dashboard Cite

Solid agrochemicals with poor thermal stability pose a huge challenge to their production and application. Herein, two low-melting-point fungicides, pyraclostrobin (ZJ) and flusilazole (FZ), were designed to form cocrystals with the high melting point fungicide of thiophanate-methyl (TM), respectively. An infrequent multistep slurry conversion crystallization process was discovered and studied, which accelerated the formation of cocrystals, and the mechanism was revealed. Oiling-out of FZ and ZJ was the key process to multistep slurry conversion crystallization. The heterogeneous system possessed the advantage of high energy, which accelerated the synthesis of cocrystals. Furthermore, the variations of physicochemical properties containing thermal stability, tap density, formulation ability, and storage stability of both the parent fungicides and cocrystals were analyzed and compared. Packing coefficient and crystal structure analysis revealed the structure–property relationships of cocrystals. The single-crystal structure showed the strong N-H···N hydrogen bonds between the FZ and TM, and N-H···O and N-H···S interactions in the ZJ-TM cocrystal. Strong hydrogen bonds stabilize the structures of cocrystals, which enables ZJ-TM and FZ-TM to be made into a greener water suspension concentrate, instead of an emulsifiable concentrate with pollution.

show abstract

Section: Resultsmentioning

confidence: 99%

Enhancing Stability and Formulation Capability of Fungicides by Cocrystallization through a Novel Multistep Slurry Conversion Process

Jin

Gong

et al. 2020

Crystal Growth & Design

View full text Add to dashboard Cite

show abstract

“…The physicochemical properties DOI: 10.1002/crat.202300169 like solubility, stability, dissolution rate, hygroscopicity, compressibility, and bioavailability of the compounds are modified through co-crystallization or organic salt formation by non-covalent and non-ionic bonds. [3][4][5][6][7] Heterocyclic compounds with nitrogen atoms have wide applications in pharmacological and biological areas. The 2-aminopyridine and its derivatives were the intermediates in the synthesis of anti-inflammatory and non-steroidal drugs.…”

Section: Introductionmentioning

confidence: 99%

Crystal Structure, Quantum Chemical, Hirshfeld Surface and Molecular Docking of Organic Molecular Salt: 2‐Amino‐5‐Chloropyridinium‐2,4‐Dihydroxybenzoate

Ponnusamy,

Madhu,

Athianna

2023

Cryst. Res. Technol.

View full text Add to dashboard Cite

An organic molecular salt, 2‐amino‐5‐chloropyridinium‐2,4‐dihydroxybenzoate (ACP‐DHB) is synthesized by the slurry method followed by crystallization from methanol. The formation of molecular salt is initially confirmed by 1H and 13C nuclear magnetic resonance (NMR) spectral data. Single crystal X‐ray diffraction (XRD) analysis shows that the crystal belongs to the monoclinic crystal system with space group, P21/n. Further, the supramolecular assembly involved the extensive network of N+−H···O− and N−H···O hydrogen bonds as well as C‐Cl···O halogen bond. Using UV‐Visible spectral data, the optical band gap is calculated and found to be 4.21 eV. Photoluminescence studies indicate the crystal has blue light emission properties. TG/DTA analysis shows that ACP‐DHB is thermally stable up to 162 °C. The quantum chemical calculations and natural bond analysis (NBO) are performed at B3LYP/6‐311G++ (d,p) basis set using Gaussian 09 software. The relative contributions of various intermolecular connections are discussed using Hirshfeld surface analysis and fingerprint plot illustration. The antibacterial and antifungal activity exhibits better inhibitory capacity against pathogens. Molecular docking revealed that ACP‐DHB efficiently binds with the 1UAG and 5KEE targets and has strong binding ability to the proteins. ADMET factors and Lipinski's rule of five are used to predict drug likeness property.

show abstract

A Proton‐Transfer Complex Containing 5‐Hydroxy‐isophthalic Acid with 3,3′‐(Piperazine‐1,4‐diylbis (methylene)) Dibenzonitrile: Structural Topology, Hirshfeld Analysis, NLO, and DFT Studies

et al. 2021

View full text Add to dashboard Cite

This work focuses on the study of a proton‐transfer complex (1) of 5‐hydroxy‐isophthalic acid (HIPA) and 3,3′‐(piperazine‐1,4‐diylbis(methylene)) dibenzonitrile (PBN). The single‐crystal XRD reveals that the HIPA and PBN molecules in complex (1) are mutually connected through intricate N+−H−O− H‐bonding interactions. Herein, close and open aperture measurement for the third‐order nonlinear optical response of the complex (1) has been investigated using the Z‐scan technique which shows its potential application in optoelectronic and photonic devices. Further, DFT calculations have been done for the HOMO‐LUMO energy gap and Mulliken atomic charge analysis which helps us to understand the proton‐transfer mechanism in the complex (1). The topological and Hirshfeld surface analysis were also achieved to understand the importance of non‐covalent interactions in the stability of the supramolecular structure and NLO properties.

show abstract

Cocrystallization of 2,3-dimethylquinoxaline with 3,5-dinitrobenzoic acid: Crystal structure, Hirshfeld surface, spectroscopic features and DFT studies

Cited by 17 publications

References 55 publications

Enhancing Stability and Formulation Capability of Fungicides by Cocrystallization through a Novel Multistep Slurry Conversion Process

Enhancing Stability and Formulation Capability of Fungicides by Cocrystallization through a Novel Multistep Slurry Conversion Process

Crystal Structure, Quantum Chemical, Hirshfeld Surface and Molecular Docking of Organic Molecular Salt: 2‐Amino‐5‐Chloropyridinium‐2,4‐Dihydroxybenzoate

A Proton‐Transfer Complex Containing 5‐Hydroxy‐isophthalic Acid with 3,3′‐(Piperazine‐1,4‐diylbis (methylene)) Dibenzonitrile: Structural Topology, Hirshfeld Analysis, NLO, and DFT Studies

Contact Info

Product

Resources

About