scholarly journals One-Dimensional Hydrogen-Bonded N–H…O in the Hybrid Phosphate: Hirshfeld Surface Analysis and DFT Quantum Chemical Calculations

2021 ◽  
Vol 15 (3) ◽  
pp. 359-368
Author(s):  
Abdellatif Rafik ◽  
◽  
Hafid Zouihri ◽  
Taoufiq Guedira ◽  
◽  
...  
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Density Functional Theory Calculations ◽  
Hirshfeld Surface ◽  
Basis Set ◽  
Hirshfeld Surface Analysis ◽  
Supramolecular Network ◽  
Perfect Agreement ◽  
Molecular Electrostatic Potential Surface

In the present work the 3D-supramolecular network is stabilized by N–H…O and O–H…O hydrogen bonds, by O…N interactions involving the organic cation and inorganic anion as checked by Hirshfeld surface analysis. The van der Waals contacts play a key role in the consolidation of the packing of 4-chloro-2-methylanilinium dihydrogenphosphate[4-CMDHP] structure. In order to support experimental results, density functional theory calculations have been performed using B3LYP functional with 3-21 G basis set. All of the obtained theoretical results are in a perfect agreement with the experimental ones. Furthermore, nonlinear optical behavior of 4-CMDHP has been investigated by determining the Hirshfeld surface, density of states and HOMO-LUMO energy gap using the same basis set. Finally, the molecular electrostatic potential surface of 4-CMDHP molecule was simulated and discussed.

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of (E)-1-(4-bromophenyl)-3-(3-fluorophenyl)prop-2-en-1-one

2019 ◽  
Vol 75 (1) ◽  
pp. 58-63 ◽  
Author(s):  
Muhamad Fikri Zaini ◽  
Ibrahim Abdul Razak ◽  
Mohamad Zahid Anis ◽  
Suhana Arshad
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Significant Contribution ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Basis Set ◽  
Hirshfeld Surface Analysis ◽  
Functional Theory ◽  
Homo Lumo

The asymmetric unit of the title halogenated chalcone derivative, C15H10BrFO, contains two independent molecules, both adopting an s-cis configuration with respect to the C=O and C=C bonds. In the crystal, centrosymmetrically related molecules are linked into dimers via intermolecular hydrogen bonds, forming rings with R 1 2(6), R 2 2(10) and R 2 2(14) graph-set motifs. The dimers are further connected by C—H...O interactions into chains parallel to [001]. A Hirshfeld surface analysis suggests that the most significant contribution to the crystal packing is by H...H contacts (26.3%). Calculations performed on the optimized structure obtained using density functional theory (DFT) at B3LYP with the 6–311 G++(d,p) basis set reveal that the HOMO–LUMO energy gap is 4.12 eV, indicating the suitability of this crystal for optoelectronic and biological applications. The nucleophilic and electrophilic binding site regions are elucidated using the molecular electrostatic potential (MEP).

scholarly journals Synthesis, X-ray crystal structure, Hirshfeld surface analysis and DFT studies of (E)-N′-(2-bromobenzylidene)-4-methylbenzohydrazide

2019 ◽  
Vol 75 (2) ◽  
pp. 109-114 ◽  
Author(s):  
Azhagan Ganapathi Anitha ◽  
Chidambaram Arunagiri ◽  
Annamalai Subashini
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Hirshfeld Surface ◽  
Basis Set ◽  
Hirshfeld Surface Analysis ◽  
Functional Theory ◽  
X Ray ◽  
Homo Lumo ◽  
Good Support

The title molecule, C15H13BrN2O, displays a trans configuration with respect to the C=N double bond. The dihedral angle between the bromo- and methyl-substituted benzene rings is 16.1 (3)°. In the crystal, molecules are connected by N—H...O and weak C—H...O hydrogen bonds, forming R 2 1(6) ring motifs and generating chains along the a–axis direction. The optimized structure generated theoretically via density functional theory (DFT) using standard B3LYP functional and 6–311 G(d,p) basis-set calculations renders good support to the experimental data. The HOMO–LUMO behaviour was elucidated to determine the energy gap. The intermolecular interactions were quantified and analysed using Hirshfeld surface analysis.

scholarly journals Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 2-(2,3-dihydro-1H-perimidin-2-yl)-6-methoxyphenol

2020 ◽  
Vol 76 (5) ◽  
pp. 605-610
Author(s):  
Ballo Daouda ◽  
Nanou Tiéba Tuo ◽  
Tuncer Hökelek ◽  
Kangah Niameke Jean-Baptiste ◽  
Kodjo Charles Guillaume ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Functional Theory ◽  
Compound C

The title compound, C18H16N2O2, consists of perimidine and methoxyphenol units, where the tricyclic perimidine unit contains a naphthalene ring system and a non-planar C4N2 ring adopting an envelope conformation with the NCN group hinged by 47.44 (7)° with respect to the best plane of the other five atoms. In the crystal, O—HPhnl...NPrmdn and N—HPrmdn...OPhnl (Phnl = phenol and Prmdn = perimidine) hydrogen bonds link the molecules into infinite chains along the b-axis direction. Weak C—H...π interactions may further stabilize the crystal structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (49.0%), H...C/C...H (35.8%) and H...O/O...H (12.0%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry indicates that in the crystal, the O—HPhnl...NPrmdn and N—HPrmdn...OPhnl hydrogen-bond energies are 58.4 and 38.0 kJ mol−1, respectively. Density functional theory (DFT) optimized structures at the B3LYP/ 6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

scholarly journals Density functional theory calculations and Hirshfeld surface analysis of propyl-para-hydroxybenzoate (PHB) for optoelectronic application

2020 ◽  
Vol 0 (0) ◽  
Author(s):  
V. Mohankumar ◽  
N. Karunagaran ◽  
M. Senthil Pandian ◽  
P. Ramasamy
Keyword(s):  
Charge Transfer ◽  
Surface Analysis ◽  
Density Functional ◽  
Hirshfeld Surface ◽  
Basis Set ◽  
Hirshfeld Surface Analysis ◽  
Frontier Molecular Orbital ◽  
Mulliken Charge ◽  
Charge Analysis ◽  
Orbital Analysis

AbstractThe geometries, electrostatic potential, Mulliken charge analysis, Natural Bond Orbital analysis and polarizabilities of propyl-para-hydroxybenzoate were calculated using B3LYP functional with 6-311++G(d,p) basis set. The calculated geometries are well matched with the experimental values. The Mullliken atomic charge analysis shows that the eventual charges are contained in the molecule. The NBO analysis explains the intramolecular charge transfer in the PHB molecule. The bonding features of the molecule were analyzed with the aid of Hirshfeld surface analysis. The frontier molecular orbital analysis showed the charge transfer obtained within the molecule. The calculated hyperpolarizability of the PHB molecule was 6.977E−30 esu and it was 8.9 times that of standard urea molecule.

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT study of N-(2-amino-5-methylphenyl)-2-(5-methyl-1H-pyrazol-3-yl)acetamide

2021 ◽  
Vol 77 (6) ◽  
pp. 638-642
Author(s):  
Gamal Al Ati ◽  
Karim Chkirate ◽  
Joel T. Mague ◽  
Nadeem Abad ◽  
Redouane Achour ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Layer Structure ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Lumo Energy ◽  
Functional Theory ◽  
Homo Lumo

The title molecule, C13H16N4O, adopts an angular conformation. In the crystal a layer structure is generated by N—H...O and N—H...N hydrogen bonds together with C—H...π(ring) interactions. Hirshfeld surface analysis indicates that the most important contributions to the crystal packing are from H...H (53.8%), H...C/C...H (21.7%), H...N/N...H (13.6%), and H...O/O...H (10.8%) interactions. The optimized structure calculated using density functional theory (DFT) at the B3LYP/ 6–311 G(d,p) level is compared with the experimentally determined structure in the solid state. The calculated HOMO–LUMO energy gap is 5.0452 eV.

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of 2-[(2-hydroxy-5-methylbenzylidene)amino]benzonitrile

2020 ◽  
Vol 76 (8) ◽  
pp. 1195-1200
Author(s):  
Md. Serajul Haque Faizi ◽  
Emine Berrin Cinar ◽  
Alev Sema Aydin ◽  
Erbil Agar ◽  
Necmi Dege ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Condensation Reaction ◽  
Three Dimensional ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Orthorhombic Space Group ◽  
Compound C ◽  
Dimensional Network

The title compound, C15H12N2O, was synthesized by condensation reaction of 2-hydroxy-5-methylbenzaldehyde and 2-aminobenzonitrile, and crystallizes in the orthorhombic space group Pbca. The phenol ring is inclined to the benzonitrile ring by 25.65 (3)°. The configuration about the C=N bond is E, stabilized by a strong intramolecular O—H...N hydrogen bond that forms an S(6) ring motif. In the crystal, C—H...O and C—H...N interactions lead to the formation of sheets perpendicular to the a axis. C—H...π interactions, forming polymeric chains along the a-axis direction, connect these sheets into a three-dimensional network. A Hirshfeld surface analysis indicates that the most important contributions for the packing arrangement are from H...H and C...H/H...C interactions. The density functional theory (DFT) optimized structure at the B3LYP/6–311 G(d,p) level is compared with the experimentally determined molecular structure and the HOMO–LUMO energy gap is given.

scholarly journals Crystal structure, Hirshfeld surface analysis and interaction energy and DFT studies of 3-{(2Z)-2-[(2,4-dichlorophenyl)methylidene]-3-oxo-3,4-dihydro-2H-1,4-benzothiazin-4-yl}propanenitrile

2019 ◽  
Vol 75 (6) ◽  
pp. 721-727 ◽  
Author(s):  
Nada Kheira Sebbar ◽  
Brahim Hni ◽  
Tuncer Hökelek ◽  
Abdelhakim Jaouhar ◽  
Mohamed Labd Taha ◽  
...  
Keyword(s):  
Crystal Structure ◽  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Boat Conformation ◽  
Compound C

The title compound, C18H12Cl2N2OS, consists of a dihydrobenzothiazine unit linked by a –CH group to a 2,4-dichlorophenyl substituent, and to a propanenitrile unit is folded along the S...N axis and adopts a flattened-boat conformation. The propanenitrile moiety is nearly perpendicular to the mean plane of the dihydrobenzothiazine unit. In the crystal, C—HBnz...NPrpnit and C—HPrpnit...OThz (Bnz = benzene, Prpnit = propanenitrile and Thz = thiazine) hydrogen bonds link the molecules into inversion dimers, enclosing R 2 2(16) and R 2 2(12) ring motifs, which are linked into stepped ribbons extending along [110]. The ribbons are linked in pairs by complementary C=O...Cl interactions. π–π contacts between the benzene and phenyl rings, [centroid–centroid distance = 3.974 (1) Å] may further stabilize the structure. The Hirshfeld surface analysis of the crystal structure indicates that the most important contributions for the crystal packing are from H...H (23.4%), H...Cl/Cl...H (19.5%), H...C/C...H (13.5%), H...N/N...H (13.3%), C...C (10.4%) and H...O/O...H (5.1%) interactions. Hydrogen bonding and van der Waals interactions are the dominant interactions in the crystal packing. Computational chemistry calculations indicate that the two independent C—HBnz...NPrpnit and C—HPrpnit...OThz hydrogen bonds in the crystal impart about the same energy (ca 43 kJ mol−1). Density functional theory (DFT) optimized structures at the B3LYP/6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of 6-bromo-3-(12-bromododecyl)-2-(4-nitrophenyl)-4H-imidazo[4,5-b]pyridine

2020 ◽  
Vol 76 (5) ◽  
pp. 677-682 ◽  
Author(s):  
Zainab Jabri ◽  
Karim Jarmoni ◽  
Tuncer Hökelek ◽  
Joel T. Mague ◽  
Safia Sabir ◽  
...  
Keyword(s):  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Hirshfeld Surface ◽  
Hirshfeld Surface Analysis ◽  
Side Chain ◽  
Functional Theory ◽  
Compound C ◽  
Homo Lumo

The title compound, C24H30Br2N4O2, consists of a 2-(4-nitrophenyl)-4H-imidazo[4,5-b]pyridine entity with a 12-bromododecyl substituent attached to the pyridine N atom. The middle eight-carbon portion of the side chain is planar to within 0.09 (1) Å and makes a dihedral angle of 21.9 (8)° with the mean plane of the imidazolopyridine moiety, giving the molecule a V-shape. In the crystal, the imidazolopyridine units are associated through slipped π–π stacking interactions together with weak C—HPyr...ONtr and C—HBrmdcyl...ONtr (Pyr = pyridine, Ntr = nitro and Brmdcyl = bromododecyl) hydrogen bonds. The 12-bromododecyl chains overlap with each other between the stacks. The terminal –CH2Br group of the side chain shows disorder over two resolved sites in a 0.902 (3):0.098 (3) ratio. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...H (48.1%), H...Br/Br...H (15.0%) and H...O/O...H (12.8%) interactions. The optimized molecular structure, using density functional theory at the B3LYP/ 6–311 G(d,p) level, is compared with the experimentally determined structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

scholarly journals Crystal structure, Hirshfeld surface analysis and DFT studies of 1-benzyl-3-[(1-benzyl-1H-1,2,3-triazol-5-yl)methyl]-2,3-dihydro-1H-1,3-benzodiazol-2-one monohydrate

2020 ◽  
Vol 76 (1) ◽  
pp. 95-101
Author(s):  
Asmaa Saber ◽  
Nada Kheira Sebbar ◽  
Tuncer Hökelek ◽  
Mohamed Labd Taha ◽  
Joel T. Mague ◽  
...  
Keyword(s):  
Hydrogen Bonds ◽  
Surface Analysis ◽  
Density Functional ◽  
Energy Gap ◽  
Crystal Packing ◽  
Close Approach ◽  
Hirshfeld Surface ◽  
Van Der Waals Interactions ◽  
Hirshfeld Surface Analysis ◽  
Dimensional Structure

In the title molecule, C24H21N5O·H2O, the dihydrobenzodiazole moiety is not quite planar, while the whole molecule adopts a U-shaped conformation in which there is a close approach of the two benzyl groups. In the crystal, chains of alternating molecules and lattice water extending along [201] are formed by O—HUncoordW...ODhyr and O—HUncoordW...NTrz (UncoordW = uncoordinated water, Dhyr = dihydro and Trz = triazole) hydrogen bonds. The chains are connected into layers parallel to (010) by C—HTrz...OUncoordW hydrogen bonds with the dihydrobenzodiazole units in adjacent layers intercalating to form head-to-tail π-stacking [centroid-to-centroid distance = 3.5694 (11) Å] interactions between them, which generates the overall three-dimensional structure. Hirshfeld surface analysis indicates that the most important contributions for the crystal packing are from H...H (52.1%), H...C/C...H (23.8%) and O...H/H...O (11.2%) interactions. Hydrogen-bonding and van der Waals interactions are the dominant interactions in the crystal packing. Density functional theory (DFT) optimized structures at the B3LYP/ 6–311 G(d,p) level are compared with the experimentally determined molecular structure in the solid state. The HOMO–LUMO behaviour was elucidated to determine the energy gap.

Sign in / Sign up

Export Citation Format

Share Document