Nucleophilic substitution approach towards 1,3-dimethylbarbituric acid derivatives—new synthetic routes and crystal structures

Mallah, Eyad; Sweidan, Kamal; Engelmann, J; Steimann, Manfred; Kühn, Norbert; Maier, Martin E.

doi:10.1016/j.tet.2011.11.093

Cited by 14 publications

(3 citation statements)

References 36 publications

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“…C(sp 3 )···O separations in 1a – m are consistently shorter than the sum of the carbon and oxygen van der Waals radii, independent of the nature of the halogen substituents at C5 and of the substituents at nitrogen atoms. For instance, the Nc value of the C(sp 3 )···O distance is 0.90 in difluorobarbituric acid 1a and 0.92 and 0.91 in one of the independent molecules in the unit cells of dichloro and dibromo dimethyl barbituric acids 1i , m , respectively. C(sp 3 )···O contacts involving C5 are typically shorter than C(sp 2 )···O contacts involving C2 and slightly longer than C(sp 2 )···O contacts involving C4/6.…”

Section: Resultsmentioning

confidence: 99%

Tetrel and Pnictogen Bonds Complement Hydrogen and Halogen Bonds in Framing the Interactional Landscape of Barbituric Acids

Kumar

Scilabra

Politzer

et al. 2020

Crystal Growth & Design

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Experimental and theoretical studies of fluoro-, chloro-, and bromo-substituted derivatives of barbituric acid and indandione show that imide protons form short hydrogen bonds and bromine or, to a lesser extent, chlorine atoms form halogen bonds. The imide nitrogen atoms act as effective pnictogen bond donors, while C(sp 2 ) and C(sp 3 ) atoms act as tetrel bond donors; the resulting N•••O and C•••O close interactions are a distinctive feature of crystal lattices in all compounds. Importantly, halogen atoms promote the electrophilicity of C(sp 3 ) sites and favor the formation of C(sp 3 )•••O close contacts. Oxygen atoms of carbonyl groups of barbituric and indandione units or of water molecules function as the interaction acceptor sites: namely, they donate electron density to hydrogen, halogen, nitrogen, and carbon atoms. Modeling of various barbituric acid derivatives indicates that the positive electrostatic potentials of π-holes orthogonal to the C(sp 2 ) carbons and σ-holes on the elongation of quasi-axial F/Cl/Br−C(sp 3 ) bonds merge to produce a single well-defined point of the most positive electrostatic potential on one face of the barbituric acids. This single local maximum of the potential on the molecular face is close to the site occupied by the oxygen forming the C(sp 3 )•••O, and C(sp 2 )•••O, short contacts observed in crystals.

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Section: Resultsmentioning

confidence: 99%

Tetrel and Pnictogen Bonds Complement Hydrogen and Halogen Bonds in Framing the Interactional Landscape of Barbituric Acids

Kumar

Scilabra

Politzer

et al. 2020

Crystal Growth & Design

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“…5 Alternatively, direct amidation utilizes reactions of free carboxylic acid with amines through thermal direct reaction or by using a metal-catalyst. 6 In continuation of our further search for new derivatives of heterocyclic moieties, [2][3][4]7 we report herein the synthesis and full characterization of compound 5 (Fig. 1).…”

Section: Introductionmentioning

confidence: 97%

Synthesis, characterization and crystal structure of pentyl 2-(1H-indole-2-carboxamido)benzoate

Kamal¹,

Khanfar²,

Al-Shamaileh³

et al. 2019

10.5267/j.ccl

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Pentyl 2-(1H-indole-2-carboxamido)benzoate (5) is obtained in good yield as stable crystals by reaction of pentyl 2-amino benzoate (6) with indole-2-carbonyl chloride acid (7) in the presence of pyridine. The crystal structure of 5 confirms the presence of intramolecular hydrogen bonding (N-H…O) which produces a six-membered ring, and the molecules are linked together by intermolecular hydrogen forces (N-H…O).

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“…A number of barbiturates are important medically due to their pharmacological properties, which include their anesthetic, sedative, anticonvulsant, and hypnotic activities. They are also used as central nervous system depressants and sedative-hypnotics [3][4][5].…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic and Molecular Docking Analysis of π-Acceptor Complexes with the Drug Barbital

et al. 2022

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The drug barbital (Bar) has a strong sedative–hypnotic effect. The intermolecular charge transfer compounds associated with the chemical reactions between Bar and some π acceptors, such as 2,6-dibromoquinone-4-chloroimide (DBQ), tetracyanoquinodimethane (TCNQ), chloranil (CHL), and chloranilic acid (CLA), have been synthesized and isolated in solid state. The synthesized products have the molecular formulas (Bar–DBQ), (Bar–TCNQ), (Bar–CHL), and (Bar–CLA) with 1:1 stoichiometry based on Raman, IR, TG, 1H NMR, XRD, SEM, and UV-visible analysis techniques. Additionally, the comparative analysis of molecular docking between the donor reactant moiety, Bar, and its four CT complexes was conducted using two neurotransmitter receptors (dopamine and serotonin). The docking results obtained from AutoDockVina software were investigated by a molecular dynamics simulation technique with 100ns run. The molecular mechanisms behind receptor–ligand interactions were also looked into. The DFT computations were conducted using theory at the B3LYP/6-311G++ level. In addition, the HOMO LUMO electronic energy gap and the CT complex’s optimal geometry and molecule electrostatic potential were examined.

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Nucleophilic substitution approach towards 1,3-dimethylbarbituric acid derivatives—new synthetic routes and crystal structures

Cited by 14 publications

References 36 publications

Tetrel and Pnictogen Bonds Complement Hydrogen and Halogen Bonds in Framing the Interactional Landscape of Barbituric Acids

Tetrel and Pnictogen Bonds Complement Hydrogen and Halogen Bonds in Framing the Interactional Landscape of Barbituric Acids

Synthesis, characterization and crystal structure of pentyl 2-(1H-indole-2-carboxamido)benzoate

Spectroscopic and Molecular Docking Analysis of π-Acceptor Complexes with the Drug Barbital

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