Synthesis, crystal structure and Hirshfeld surface analysis of diethyl 2,6-dimethyl-4-(thiophen-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate

Quoc, Trung Vu; Thuy, Duong Tran Thi; Ngoc, Thanh Phung; Quoc, Manh Vu; Nguyen, Hien Minh; Khanh, Linh Duong; Quang, Anh Tu; Meervelt, Luc Van

doi:10.1107/s2056989019015081

Cited by 2 publications

(1 citation statement)

References 23 publications

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“…The four related compounds found as a result of the search for '2,6-diamino-4-(thiophen-2-yl)pyridine-3,5-dicarbonitrile' in the Cambridge Structure Database (CSD, Version 5.42, update of September 2021; Groom et al, 2016) are MUCLAA (Vu Quoc et al, 2019), WOJCIJ (Vishnupriya et al, 2014a), WOPLAQ (Vishnupriya et al, 2014b) and DOPWOW (Vishnupriya et al, 2014c).…”

Section: Database Surveymentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 2-amino-6-[(1-phenylethyl)amino]-4-(thiophen-2-yl)pyridine-3,5-dicarbonitrile

Naghiyev¹,

Khrustalev²,

Asadov³

et al. 2023

Acta Cryst E

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In the title compound, C19H15N5S, the thiophene ring is disordered in a 0.6:0.4 ratio by an approximate 180° rotation of the ring around the C—C bond linking it to the pyridine ring. In the crystal, the molecules are linked by N—H...N hydrogen bonds into dimers with an R 2 2(12) motif, forming chains along the b-axis direction. These chains are connected to each other by further N—H...N hydrogen bonds, forming a three-dimensional network. Furthermore, N—H...π and π–π [centroid–centroid separations = 3.899 (8) and 3.7938 (12) Å] interactions also contribute to the crystal cohesion. A Hirshfeld surface analysis indicated that the most important contributions to the surface contacts are from H...H (46.1%), N...H/H...N (20.4%) and C...H/H...C (17.4%) interactions.

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Section: Database Surveymentioning

confidence: 99%

Crystal structure and Hirshfeld surface analysis of 2-amino-6-[(1-phenylethyl)amino]-4-(thiophen-2-yl)pyridine-3,5-dicarbonitrile

Naghiyev¹,

Khrustalev²,

Asadov³

et al. 2023

Acta Cryst E

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Fluorescent properties of some polythiophenes synthesized from 2‐(thiophen‐3‐yl)acetohydrazide and acetophenone

Linh

Hùng

Oanh

et al. 2020

Vietnam Journal of Chemistry

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In this study, new polythiophenes containing hydrazone groups from derivatives of acetophenone were synthesized by chemical oxidative coupling polymerization. Ultraviolet‐visible spectroscopy (UV‐Vis) combined with infrared (IR) analyses proved the supposed structure of novel polythiophenes and proved conformance of the expected synthetic method. Morphology and surface properties of the synthesized polymers were investigated by field‐emission scanning electron microscopy (FE‐SEM). Thermal gravimetry analysis (TGA) has been reported that there was still the presence of small FeCl3 catalyst in polymers and polymers had a stable thermal stability under air atmosphere. The polymers displayed fluorescence emissions at about 590 nm attributed to the π‐conjugated polythiophene. Polymers without doping have a good electrical conductivity (around 4.03×10–7 S/cm at 1 MHz).

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Synthesis, crystal structure and Hirshfeld surface analysis of diethyl 2,6-dimethyl-4-(thiophen-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate

Abstract: In the title 1,4-dihydropyridine derivative, the 1,4-dihydropyridine ring makes an angle of 82.19 (13)° with the thiophene ring. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds as well as C—H⋯π interactions link the molecules into a three-dimensional network.

Cited by 2 publications

References 23 publications

Crystal structure and Hirshfeld surface analysis of 2-amino-6-[(1-phenylethyl)amino]-4-(thiophen-2-yl)pyridine-3,5-dicarbonitrile

Crystal structure and Hirshfeld surface analysis of 2-amino-6-[(1-phenylethyl)amino]-4-(thiophen-2-yl)pyridine-3,5-dicarbonitrile

Fluorescent properties of some polythiophenes synthesized from 2‐(thiophen‐3‐yl)acetohydrazide and acetophenone

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Synthesis, crystal structure and Hirshfeld surface analysis of diethyl 2,6-dimethyl-4-(thiophen-3-yl)-1,4-dihydropyridine-3,5-dicarboxylate

Abstract: In the title 1,4-di­hydro­pyridine derivative, the 1,4-di­hydro­pyridine ring makes an angle of 82.19 (13)° with the thio­phene ring. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds as well as C—H⋯π inter­actions link the mol­ecules into a three-dimensional network.

Cited by 2 publications

References 23 publications

Crystal structure and Hirshfeld surface analysis of 2-amino-6-[(1-phenylethyl)amino]-4-(thiophen-2-yl)pyridine-3,5-dicarbonitrile

Crystal structure and Hirshfeld surface analysis of 2-amino-6-[(1-phenylethyl)amino]-4-(thiophen-2-yl)pyridine-3,5-dicarbonitrile

Fluorescent properties of some polythiophenes synthesized from 2‐(thiophen‐3‐yl)acetohydrazide and acetophenone

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Abstract: In the title 1,4-dihydropyridine derivative, the 1,4-dihydropyridine ring makes an angle of 82.19 (13)° with the thiophene ring. In the crystal, N—H⋯O and C—H⋯O hydrogen bonds as well as C—H⋯π interactions link the molecules into a three-dimensional network.