2D hydrogen bonded organic framework (2D-HOF) in benzodioxane-coupled-pyridine as a charge carrier: Synthesis, structural, quantum computational investigation

Indole-arylpiperazine derivatives have exhibited good selectivity for the α1A-adrenoceptor, but the structure-activity-binding mechanism relationship remains unclear. In the current study, three compounds (1, 2 and 3) were investigated through single-crystal X-ray diffraction analysis, density functional theory (DFT) calculations and molecular docking using a homology model of the α1A receptor. Compounds 1 and 3 form H-bonds networks to stabilize their three-dimensional structures, while C–H···π interactions play a significant role in the packing of 2. Based on DFT-optimized conformations, the HOMO-LUMO energy gaps and molecular electrostatic potential (MEP) were theoretically calculated at the B3LYP/6-311G (d, p) level of theory. Chemical reactivity increases in the order of 3 < 2 < 1, and the maximum positive region of the MEP maps is mainly localized over the NH group. The binding mechanisms of ligand-α1A-adrenoceptor complexes were illustrated by molecular docking. Binding to Gln177 of the second extracellular loop region via hydrogen bonds is likely to be essential for α1A-selective antagonists. The present work sheds light on the studies of structure-activity-binding mechanism and aids in the design of α1A antagonists with high selectivity.

Crystallographic analysis, Hirshfeld surface investigation, and DFT calculations of 2-phenoxy-triazoloquinazoline molecule: Implications for drug design

An arylsulfonamide compound, methyl-2-methyl-2-(4-methylphenyl)sulfonamido propanoate, (1), has been synthesised and structurally characterised. Compound (1) has a staggered conformation relative to the S–N bond. The DFT-optimised molecular geometry of (1) agrees closely with that obtained from the crystallographic study. The crystal exhibits cooperation of N–H···O hydrogen bonds with C–H···O and C–H···π(arene) interactions, resulting in a three-dimensional framework featuring R2 2(8) and R2 2(10) synthons. The effect of substitution in different arylsulfonamides retrieved from the Cambridge Structural Database (CSD) on the formation of supramolecular synthons has been analysed in terms of graph-set notation. Hydrogen-bond based interactions in (1) have been complemented by molecular electrostatic potential (MEP) surface calculation. Hirshfeld surface analyses of (1) and a few related arylsulfonamides retrieved from the CSD indicate that about 80% of the Hirshfeld surface areas in these compounds are due to H···H and O···H contacts.

Hydroxy Derivatives of Poststerone and Its Nontrivial 13(14→8)-Abeo-analogues: Synthesis, Crystal Packing, and Intermolecular Hydrogen Bonds

Tin oxides (SnO2) have been widely utilized in electronics, nanolithography, and catalysis. As the atomically precise models of SnO2, tin-oxo clusters (TOCs) not only provide opportunities for mech...

Molecular docking/dynamics simulations, MEP analysis, and pharmacokinetics prediction of some withangulatin A derivatives as allosteric glutaminase C inhibitors in breast cancer

Structural characterization and Hirshfeld surface analysis of racemic baclofen

ABSTRACTA new bicyclononane derivative, 1,1′-(2,6-dihydroxy-2,6-dimethyl-3,7-dioxa-bicyclo[3.3.1]nonane-1,5-diyl) diethanone dihydrate (1), has been synthesized and structurally characterized by the single-crystal X-ray diffraction technique. In the solid-state structure of the compound, molecular units are interlinked via strong hydrogen bonds as well as non-classical weak hydrogen bonds leading to a three-dimensional supramolecular architecture. Solid-state DFT optimized geometry in (1) agrees closely with that obtained from the crystallographic analysis. The C(dioxa-bicyclononane)–H … O(hydroxy) hydrogen bond generates cyclic (10) ring in (1) which are further connected through C–H … O and O–H … O hydrogen bonds into a three-dimensional framework in the title compound. Hirshfeld surface analysis of the title compound along with some related nonane derivatives retrieved from the Cambridge Structural Database shows that the most of the Hirshfeld surface area in this class of compounds is due to H … H and O … H interactions.

Chemoselective synthesis, X-ray characterization and DFT studies of new organic single crystal: S-(2-aminophenyl) cyclohexylcarbamothioate

The interplay of strong and weak hydrogen bonds, dipole–dipole interactions, and aromatic interactions of o- and p-nitroaniline derivatives was studied by combining crystal structure analysis and density functional theory (DFT) calculations. Crystal structures of four 2-nitroaniline derivatives, 2-((2-nitrophenyl)amino)ethyl methanesulfonate (1A), 2-((2-nitrophenyl)amino)ethyl 4-methylbenzenesulfonate (2A), N,N′-((1,3-phenylenebis(oxy))bis(ethane-2,1-diyl))bis(2-nitroaniline) (3A), and N-(2-chloroethyl)-2-nitroaniline (4A), and crystal structures of three 4-nitroaniline derivatives, 2-((4-nitrophenyl)amino)ethyl methanesulfonate (1B), 2-((4-nitrophenyl)amino)ethyl 4-methylbenzenesulfonate (2B), and tert-butyl-(2-((4-nitrophenyl)amino)ethyl) carbonate (5B), were analyzed with regard to intra- and intermolecular hydrogen bonding and π–π interactions. The effect of o/p-substitution on π-electron distribution, aromaticity of the nitroaniline ring, and relative strength of intra- and intermolecular weak interactions were compared using HOMA indices, Hirshfeld surfaces, and DFT calculations. The 2-nitroaniline derivatives contain an intramolecular hydrogen bond between amino and nitro groups, creating a six-membered chelate ring, which formed pseudostacked structures with aromatic rings. van der Waals corrected DFT calculations showed that stacking of a phenyl and a chelate ring contributed significantly to the dimerization of 1A and 2A. Therefore, it can be concluded that the phenyl–chelate interactions are an important factor in stacking of the monomers in addition to C–H···O hydrogen bonding. In 4-nitroaniline derivatives, intermolecular N–H···O hydrogen bonds were in a significant role in packing, creating hydrogen-bonded dimers in 1B and 2B, and hydrogen-bonded chains in 5B.

Synthesis, crystal structures, computational studies and antimicrobial activity of new designed bis((5-aryl-1,3,4-oxadiazol-2-yl)thio)alkanes

Synthesis, structural characterization, and Hirshfeld surface analysis of novel NLO active 1-methyl-1,3,5,7-tetraazaadamantan-1-ium 3-carboxy-5-nitrobenzoate hydrate

Crystal growth, structural, vibrational, spectroscopic studies of novelly synthesized NLO active melaminium sulfamate single crystal: Experimental and theoretical approach

Optical, vibrational, NBO, first-order molecular hyperpolarizability and Hirshfeld surface analysis of a nonlinear optical chalcone

Synthesis, crystal structure, spectroscopic, quantum chemical investigation, molecular docking and ADMET prediction of 2(E)-3-(anthracen-9-yl)-1-(1-methyl-1H-pyrrol-2-yl) prop-2-en-1-one