scholarly journals Microwave Assisted Synthesis, Antifungal Activity, and DFT Study of Some Novel Triazolinone Derivatives

2015 ◽  
Vol 2015 ◽  
pp. 1-7
Author(s):  
Na-Bo Sun ◽  
Jian-Zhong Jin ◽  
Fang-Yue He
Keyword(s):  
Antifungal Activity ◽  
Geometry Optimization ◽  
Pythium Ultimum ◽  
Basis Set ◽  
Orbital Energy ◽  
Microwave Assisted Synthesis ◽  
Good Activity ◽  
Full Geometry Optimization ◽  
H Nmr ◽  
Multistep Reaction

A series of some novel 1,2,4-triazol-5(4H)-one derivatives were designed and synthesized under microwave irradiation via multistep reaction. The structures of 1,2,4-triazoles were confirmed by1H NMR, MS, FTIR, and elemental analysis. The antifungal activities of 1,2,4-triazoles were determined. The antifungal activity results indicated that the compounds5c,5f, and5hexhibited good activity againstPythium ultimum, and the compounds5band5cdisplayed good activity againstCorynespora cassiicola. Theoretical calculation of the compound5cwas carried out with B3LYP/6-31G (d). The full geometry optimization was carried out using 6-31G(d) basis set, and the frontier orbital energy and electrostatic potential were discussed, and the structure-activity relationship was also studied.

scholarly journals Synthesis, Crystal Structure, and Theoretical Studies of N-(4-((4-chlorobenzyl)oxy)phenyl)-4- (trifluoromethyl)pyrimidin-2-amine

2013 ◽  
Vol 2013 ◽  
pp. 1-5 ◽  
Author(s):  
Jian-Chang Jin ◽  
Zhao-Hui Sun ◽  
Ming-Yan Yang ◽  
Jing Wu ◽  
Xing-Hai Liu
Keyword(s):  
Title Compound ◽  
Geometry Optimization ◽  
Basis Set ◽  
Orbital Energy ◽  
Monoclinic Space Group ◽  
X Ray Diffraction ◽  
Full Geometry Optimization ◽  
X Ray ◽  
Compound C ◽  
Frontier Orbital Energy

The title compound (C18H13ClF3N3O) were synthesized and recrystallized from CH3OH. The compound was characterized byH1NMR, MS, HRMS, and X-ray diffraction. The compound crystallized in the monoclinic space groupP2(1)/nwitha=8.2354(14),b=12.686(2),c=16.633(3) Å,α=90,β=97.951(3),γ=90∘,V=1721.0(5)  Å3,Z=4,andR=0.0376for 1933 observed reflections withI>2σ(I).X-ray analysis reveals that intermolecular N–H⋯N interactions exist in the adjacent molecules. Theoretical calculation of the title compound was carried out with HF/6-31G(d,p), B3LYP/6-31G(d,p). The full geometry optimization was carried out using 6-31G(d,p)basis set and the frontier orbital energy. The optimized geometric bond lengths and bond angles obtained by using HF and DFT (B3LYP) showed the best agreement with the experimental data.

scholarly journals Distinctive Supramolecular Features of β-Cyclodextrin Inclusion Complexes with Antidepressants Protriptyline and Maprotiline: A Comprehensive Structural Investigation

2021 ◽  
Vol 14 (8) ◽  
pp. 812
Author(s):  
Thammarat Aree
Keyword(s):  
Inclusion Complexes ◽  
Density Functional ◽  
Water Solubility ◽  
Geometry Optimization ◽  
Binding Constants ◽  
Basis Set ◽  
Full Geometry Optimization ◽  
Basis Set Superposition Error ◽  
X Ray ◽  
Molecular Stability

Depression, a global mental illness, is worsened due to the coronavirus disease 2019 (COVID-2019) pandemic. Tricyclic antidepressants (TCAs) are efficacious for the treatment of depression, even though they have more side effects. Cyclodextrins (CDs) are powerful encapsulating agents for improving molecular stability, water solubility, and lessening the undesired effects of drugs. Because the atomic-level understanding of the β-CD–TCA inclusion complexes remains elusive, we carried out a comprehensive structural study via single-crystal X-ray diffraction and density functional theory (DFT) full-geometry optimization. Here, we focus on two complexes lining on the opposite side of the β-CD–TCA stability spectrum based on binding constants (Kas) in solution, β-CD–protriptyline (PRT) 1—most stable and β-CD–maprotiline (MPL) and 2—least stable. X-ray crystallography unveiled that in the β-CD cavity, the PRT B-ring and MPL A-ring are aligned at a nearly perfect right angle against the O4 plane and primarily maintained in position by intermolecular C–H···π interactions. The increased rigidity of the tricyclic cores is arising from the PRT -CH=CH- bridge widens, and the MPL -CH2–CH2- flexure narrows the butterfly angles, facilitating the deepest and shallower insertions of PRT B-ring (1) and MPL A-ring (2) in the distorted round β-CD cavity for better complexation. This is indicated by the DFT-derived complex stabilization energies (ΔEstbs), although the complex stability orders based on Kas and ΔEstbs are different. The dispersion and the basis set superposition error (BSSE) corrections were considered to improve the DFT results. Plus, the distinctive 3D arrangements of 1 and 2 are discussed. This work provides the first crystallographic evidence of PRT and MPL stabilized in the β-CD cavity, suggesting the potential application of CDs for efficient drug delivery.

Ab initio studies on amides: conformational preferences of formimide and barriers to interconversion of the conformers

1980 ◽  
Vol 33 (8) ◽  
pp. 1635 ◽  
Author(s):  
L Radom ◽  
NV Riggs
Keyword(s):  
Ground State ◽  
Room Temperature ◽  
Geometry Optimization ◽  
Basis Set ◽  
Partial Geometry ◽  
Electrostatic Repulsion ◽  
Full Geometry Optimization ◽  
Vapour State ◽  
Conformational Preferences ◽  
Model Transition

Formimide (diformamide), the parent of the diacylamines, is capable of existing in three basic ground-state conformations about the N-C bonds. Full geometry optimization with the STO-3G basis set predicts that all three conformers are fully coplanar, that the E,E (1) and E,Z(3) conformers are of similar energy, and that the Z,Z (2) conformer is of somewhat higher energy (by 11 kJ mol-1); 4-31G evaluation of the energies suggests that (2) is by far the least stable and that (1) is of higher energy than (3) by 6.5 kJ mol-1. Analysis of the calculated charge distribution suggests that (2) is destabilized by electrostatic repulsion. These results are consistent with experimental conclusions that planar (3) is strongly preferred in the vapour state at room temperature and that (2) has not been observed in the vapour state or in solution. Partial geometry optimization with the STO-3G basis set of model transition states for internal rotation suggests a barrier height of 52 kJ mol-1 (72 kJ mol-1 when evaluated with the 4-31G basis set) for the conversion (3) → (1).

Theoretical and experimental analysis of porphyrin derivatives with suitable anchoring groups for DSSC applications

2017 ◽  
Vol 21 (02) ◽  
pp. 88-102 ◽  
Author(s):  
Nora A. Sánchez-Bojorge ◽  
Simón Flores-Armendáriz ◽  
María E. Fuentes-Montero ◽  
Victor H. Ramos-Sánchez ◽  
Gerardo Zaragoza-Galán ◽  
...  
Keyword(s):  
Energy Levels ◽  
Dye Sensitized Solar Cells ◽  
Semiempirical Method ◽  
Basis Set ◽  
Orbital Energy ◽  
Geometrical Parameters ◽  
H Nmr ◽  
Porphyrin Derivatives ◽  
Lowest Unoccupied Molecular Orbital ◽  
Anchoring Groups

In this contribution, different porphyrin derivatives were experimentally synthesized and theoretically analyzed using several electronic structure methods to study the geometrical and electronic properties of A4, trans-A2B[Formula: see text]and A3B porphyrins bearing several functional groups (–OH, –COOH, -3,5-di-[Formula: see text]Bu, –OCH2CH2CH2COOEt and –OMe) suitable to be employed as dyes in Dye Sensitized Solar Cells (DSSC). A4 (R [Formula: see text] -H, -OMe, -OH, -3,5-di-tert-butyl, –OCH2CH2CH2COOEt) and A3B (R[Formula: see text][Formula: see text]R[Formula: see text][Formula: see text]R[Formula: see text][Formula: see text]–H; R[Formula: see text][Formula: see text]–OH and R[Formula: see text][Formula: see text]-3,5-di-[Formula: see text]Bu) porphyrins were synthesized and characterized by UV-vis and 1H NMR spectroscopies for comparison. The geometrical parameters were analyzed in the ground state and gas phase using the semiempirical method PM6 and the DFT functionals M06-2X and B3LYP, in combination with the 6-31G(d), DZVP and TZVP basis set. For calculations of the electronic and excited state properties, CAM-B3LYP, M06-2X and HSE06, using SMD as solvation model, were applied. This study revealed that HSE06/DZVP protocol is the best methodology to simulate electronic spectra in these porphyrin derivatives. Indeed, whereas substituent groups did not significantly affect the geometrical structure of the porphyrin derivatives studied, they do influence their electronic structures, mainly in the LUMO (lowest unoccupied molecular orbital) energy levels.

scholarly journals Structure, MESP and HOMO-LUMO study of 10-Acetyl- 10H-phenothiazine 5-oxide using vibrational spectroscopy and quantum chemical methods

BIBECHANA ◽  
2012 ◽  
Vol 9 ◽  
pp. 38-49
Author(s):  
Bhawani Datt Joshi ◽  
Poonam Tandon ◽  
Sudha Jain
Keyword(s):  
Molecular Orbital ◽  
Density Functional ◽  
Energy Gap ◽  
Geometry Optimization ◽  
Basis Set ◽  
Orbital Energy ◽  
Potential Energy Distribution ◽  
Hartree Fock ◽  
Quantum Chemical Methods ◽  
B3lyp Method

In this communication, we have presented the geometry optimization, complete vibrational study with potential energy distribution (PED) and frontier orbital energy gap for the 10-Acetyl-10H-phenothiazine 5-oxide (APTZ) molecule using ab initio Hartree-Fock (HF) and density functional theory (DFT/B3LYP) method employing 6-311++G(d,p) basis set. The calculated IR and Raman spectra with their intensities, molecular electrostatic potential (MESP) surface and highest occupied molecular orbital (HOMO) - lowest unoccupied molecular orbital (LUMO) plot have been given. DOI: http://dx.doi.org/10.3126/bibechana.v9i0.7151 BIBECHANA 9 (2013) 38-49

Spectroscopic investigations and DFT studies of synthesized 4-acetamidophenyl 3,4,5-trimethoxybenzoate and 4-acetyl phenyl 3,4,5-trimethoxybenzoate a novel conjugate of gallic acid

2020 ◽  
Vol 17 ◽  
Author(s):  
Sangeeta Srivastava ◽  
Nadeem Ahmad Ansari ◽  
Sadaf Aleem
Keyword(s):  
Gallic Acid ◽  
Density Functional ◽  
Energy Gap ◽  
Basis Set ◽  
Major Constituent ◽  
Orbital Energy ◽  
Reactivity Descriptors ◽  
Homo And Lumo ◽  
Electrophilic Reactivity ◽  
Global And Local

: Gallic acid is abundantly found in amla (Phyllanthus emblica), a deciduous of the family phyllanthaceae. Gallic acid, the major constituent of the plant was methylated to 3,4,5 trimethoxy gallic acid, which then underwent steglich esterification first with paracetamol and then with 4-hydroxy acetophenone to yield 4-acetamidophenyl 3,4,5-trimethoxybenzoate and 4-acetyl phenyl 3,4,5-trimethoxybenzoate “respectively”. 1H NMR, 13C NMR, UV, FT-IR and mass spectroscopy were used to characterize the synthesized compounds. Density functional theory (B3YLP) using 6-31G (d,p) basis set have been used for quantum chemical calculations. AIM (Atom in molecule) approach depicted weak molecular interactions within the molecules whereas the reactive site and reactivity within the molecule were examined by global and local reactivity descriptors. The HOMO and LUMO energies and frontier orbital energy gap were calculated by time dependant DFT approach using IEFPCM model. Small value for HOMO–LUMO energy gap indicated that easier charge transfer occurs within compound 4. The nucleophilic and electrophilic reactivity were determined by MEP (molecular electrostatic potential) experiment. Polarizability, dipole moment, and first hyperpolarizability values were calculated to depict the NLO (nonlinear optical) property of both the synthesized compounds. The antimicrobial activity was also carried out and broad spectrum antibacterial activity against several strains of bacteria and certain unicellular fungi were exhibited by synthesized compound 3.

Microwave Assisted Synthesis and Antifungal Activity of Some Novel Thioethers Containing 1,2,4-triazolo[4,3-a] pyridine Moiety

2016 ◽  
Vol 13 (6) ◽  
pp. 521-525 ◽  
Author(s):  
Zhi-Wen Zhai ◽  
Yan-Xia Shi ◽  
Ming-Yan Yang ◽  
Wen Zhao ◽  
Zhao-Hui Sun ◽  
...  
Keyword(s):  
Antifungal Activity ◽  
Microwave Assisted Synthesis ◽  
Microwave Assisted ◽  
Pyridine Moiety

scholarly journals ß-Cyclodextrin Inclusion Complexes with Catechol-Containing Antioxidants Protocatechuic Aldehyde and Protocatechuic Acid—An Atomistic Perspective on Structural and Thermodynamic Stabilities

Molecules ◽  
2021 ◽  
Vol 26 (12) ◽  
pp. 3574
Author(s):  
Thammarat Aree
Keyword(s):  
Inclusion Complexes ◽  
Protocatechuic Acid ◽  
Inclusion Complexation ◽  
Geometry Optimization ◽  
Therapeutic Effects ◽  
Full Geometry Optimization ◽  
Oh Groups ◽  
X Ray ◽  
Protocatechuic Aldehyde ◽  
Crystal Contacts

Protocatechuic aldehyde (PCAL) and protocatechuic acid (PCAC) are catechol derivatives and have broad therapeutic effects associated with their antiradical activity. Their pharmacological and physicochemical properties have been improved via the cyclodextrin (CD) encapsulation. Because the characteristics of b-CD inclusion complexes with PCAL (1) and PCAC (2) are still equivocal, we get to the bottom of the inclusion complexation by an integrated study of single-crystal X-ray diffraction and DFT full-geometry optimization. X-ray analysis unveiled that PCAL and PCAC are nearly totally shielded in the b-CD wall. Their aromatic rings are vertically aligned in the b-CD cavity such that the functional groups on the opposite side of the ring (3,4-di(OH) and 1-CHO/1-COOH groups) are placed nearby the O6–H and O2–H/O3–H rims, respectively. The preferred inclusion modes in 1 and 2 help to establish crystal contacts of OH×××O H-bonds with the adjacent b-CD OH groups and water molecules. By contrast, the DFT-optimized structures of both complexes in the gas phase are thermodynamically stable via the four newly formed host–guest OH⋯O H-bonds. The intermolecular OH×××O H-bonds between PCAL/PCAC 3,4-di(OH) and b-CD O6–H groups, and the shielding of OH groups in the b-CD wall help to stabilize these antioxidants in the b-CD cavity, as observed in our earlier studies. Moreover, PCAL and PCAC in distinct lattice environments are compared for insights into their structural flexibility.

Synthesis, characterization and computational studies of 1,3-bis[(E)-furan-2-yl)methylene]urea and 1,3-bis[(E)-furan-2-yl)methylene]thiourea

2020 ◽  
Vol 0 (0) ◽  
Author(s):  
Kazeem Adelani Alabi ◽  
Ibrahim Olasegun Abdulsalami ◽  
Moriam Dasola Adeoye ◽  
Shukurat Modupe Aderinto ◽  
Rasheed Adewale Adigun
Keyword(s):  
Energy Surface ◽  
Salmonella Typhi ◽  
Basis Set ◽  
Frontier Molecular Orbital ◽  
Thiourea Derivatives ◽  
H Nmr ◽  
Complete Relaxation ◽  
Cercospora Zeae Maydis ◽  
Global Parameters ◽  
C Nmr

AbstractUrea and thiourea derivatives: 1,3-bis[(E)-furan-2-yl)methylene]urea (BFMU) and 1,3-bis[(E)-furan-2-yl)methylene]thiourea (BFMT) were synthesized and characterized by spectrometry analyses (UV, IR, 1H NMR and 13C NMR). They were screened for antibacterial (Salmonella typhi, Staphylococcus aureus, Pseudomonas aeruginosa, Xanthomonas axonopodis and Streptococcus bovis) and antifungal (Fusarium oxysporum, Colletotrichum gloeosporioides and Cercospora zeae-maydis) activities. Quantum chemical calculations of frontier molecular orbital energies (EHOMO and ELUMO), and their associated global parameters were carried out by DFT levels of theory, with complete relaxation in the potential energy surface using 6-31G* basis set (DFT/B3LYP/6-31G*). Azomethine functional groups (C=N) appeared at δ 7.6 ppm and δ 7.0 ppm in the proton spectra, the peaks between δ 105 and δ 160 ppm of 13C spectra represent the methylene carbons (C=C). BFMU is a better inhibitor of P. aeruginosa and S. bovis, while BFMT is a better inhibitor of S. typhi, S. aureus and X. axonopodis and the fungi isolates (F. oxysporum, C. gloeosporioides and C. zeae-maydis) used. The global parameters agreed favorably with the experimental results, indicating the higher activity of BFMT.

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