Surprisingly regular structure–property relationships between C–O bond distances and methoxy group torsional potentials: An ab initio and density functional study

Klocker, Johanna; Karpfen, Alfred; Wolschann, Peter

doi:10.1016/s0166-1280(03)00413-5

Cited by 17 publications

(6 citation statements)

References 27 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compare these theoretically calculated geometric parameters with experimental data from a crystallographic analysis [ 79 ], knowing that the relative deviation Δ for a geometric parameter X is expressed as a percentage by the relation:

…”

Section: Resultsmentioning

confidence: 99%

A Competition between Hydrogen, Stacking, and Halogen Bonding in N-(4-((3-Methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)selanyl)phenyl)acetamide: Structure, Hirshfeld Surface Analysis, 3D Energy Framework Approach, and DFT Calculation

Gouda

El‐Lateef

Khalaf

et al. 2022

IJMS

View full text Add to dashboard Cite

N-(4-((3-Methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)selanyl)phenyl)acetamide (5), C19H15NO3Se, was prepared in two steps from 4,4′-diselanediyldianiline (3) via reduction and subsequent nucleophilic reaction with 2-methyl-3-bromo-1,4-naphthalenedione, followed by acetylation with acetic anhydride. The cytotoxicity was estimated against 158N and 158JP oligodendrocytes and the redox profile was also evaluated using different in vitro assays. The technique of single-crystal X-ray diffraction is used to confirm the structure of compound 5. The enantiopure 5 crystallizes in space group P21 with Flack parameter 0.017 (8), exhibiting a chiral layered absolute structure. Molecular structural studies showed that the crystal structure is foremost stabilized by N-H···O and relatively weak C-H···O contacts between molecules, and additionally stabilized by weak C-H···π and Se···N interactions. Hirshfeld surface analysis is used to quantitatively investigate the noncovalent interactions that stabilize crystal packing. Framework energy diagrams were used to graphically represent the stabilizing interaction energies for crystal packing. The analysis of the energy framework shows that the interactions energies of and C-H···π and C-O···π are primarily dispersive and are the crystal’s main important forces. Density functional theory (DFT) calculations were used to determine the compound’s stability, chemical reactivity, and other parameters by determining the HOMO-LUMO energy differences. The determination of its optimized surface of the molecular electrostatic potential (MEP) was also carried out. This study was conducted to demonstrate both the electron-rich and electron-poor sites.

show abstract

…”

Section: Resultsmentioning

confidence: 99%

A Competition between Hydrogen, Stacking, and Halogen Bonding in N-(4-((3-Methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)selanyl)phenyl)acetamide: Structure, Hirshfeld Surface Analysis, 3D Energy Framework Approach, and DFT Calculation

Gouda

El‐Lateef

Khalaf

et al. 2022

IJMS

View full text Add to dashboard Cite

show abstract

“…1). Most research thus far has been limited to first and second row elements in the periodic table [4,8,9, and only a few studies considered molecules with other atom types, such as Br [76,101], Ge [70], As [70], Se [115] and Te [125] (see Figure 1). A less biased assessment of the performance of DFT for torsional profiles should cover larger domains of compound space, including molecules with third-row atoms.…”

Section: Introductionmentioning

confidence: 99%

“…An overview of the existing literature indicates a severe lack of chemical diversity in systems studied so far (Figure ). Most research thus far has been limited to first and second row elements in the periodic table ,,,− …”

Section: Introductionmentioning

confidence: 99%

“…5,11 An overview of the existing literature indicates a severe lack of chemical diversity in systems studied so far (Figure 1). Most research thus far has been limited to first and second row elements in the periodic table 4,8,9,11−126 and only a few studies considered molecules with other atom types, such as Br, 76,101 Ge, 70 As, 70 Se, 115 and Te 127 (see Figure 1).…”

Section: Introductionmentioning

confidence: 99%

See 1 more Smart Citation

Torsional Potentials of Glyoxal, Oxalyl Halides, and Their Thiocarbonyl Derivatives: Challenges for Popular Density Functional Approximations

Tahchieva

Bakowies

Ramakrishnan

et al. 2018

J. Chem. Theory Comput.

View full text Add to dashboard Cite

The reliability of popular density functionals was studied for the description of torsional profiles of 36 molecules: glyoxal, oxalyl halides, and their thiocarbonyl derivatives. HF and 18 functionals of varying complexity, from local density to range-separated hybrid approximations and double-hybrid, have been considered and benchmarked against CCSD(T)-level rotational profiles. For molecules containing heavy halogens, most functionals fail to reproduce barrier heights accurately and a number of functionals introduce spurious minima. Dispersion corrections show no improvement. Calibrated torsion-corrected atom-centered potentials rectify the shortcomings of PBE and also improve on σ-hole based intermolecular binding in dimers and crystals.

show abstract

“…There is only limited information related to the compounds containing methoxy groups. This relates to the methoxy group rotation in anisole [4], relationships between the C-O bond length and the methoxy group rotational potentials [5] and ab initio calculations for anisole [6]. There are several other communications connected with the methoxy groups but in rather very complicated molecular structures.…”

Section: Introductionmentioning

confidence: 99%

Structure and Vibrational Spectra of 1,3,5-Trimethoxybenzene

2007

View full text Add to dashboard Cite

Inelastic neutron scattering infrared and Raman spectra of the crystalline 1,3,5-trimethoxybenzene were measured and compared with simulated ones by using the Gaussian 98 and DMol3 programs at density functional theory methods. Application of the double numerical plus polarization basis set for the crystalline state within the local density Perdew and Wang (PWC functionals) approximation quite well reproduces the low frequency bands related to the methyl group librational modes, which are very sensitive to molecular interactions. Infrared spectra for the crystalline sample and CCl 4 solution show spectacularly the change of low frequency modes by going from the symmetric D 3h molecules in the gas phase to asymmetric ones in the crystal.

show abstract

Surprisingly regular structure–property relationships between C–O bond distances and methoxy group torsional potentials: An ab initio and density functional study

Cited by 17 publications

References 27 publications

A Competition between Hydrogen, Stacking, and Halogen Bonding in N-(4-((3-Methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)selanyl)phenyl)acetamide: Structure, Hirshfeld Surface Analysis, 3D Energy Framework Approach, and DFT Calculation

A Competition between Hydrogen, Stacking, and Halogen Bonding in N-(4-((3-Methyl-1,4-dioxo-1,4-dihydronaphthalen-2-yl)selanyl)phenyl)acetamide: Structure, Hirshfeld Surface Analysis, 3D Energy Framework Approach, and DFT Calculation

Torsional Potentials of Glyoxal, Oxalyl Halides, and Their Thiocarbonyl Derivatives: Challenges for Popular Density Functional Approximations

Structure and Vibrational Spectra of 1,3,5-Trimethoxybenzene

Contact Info

Product

Resources

About