Electronic substituent effect on Se-H⋯N hydrogen bond: A computational study of para-substituted pyridine-SeH2 complexes

Jaju, Karan; Pal, Dhritabrata; Chakraborty, Amrita; Chakraborty, Shamik

doi:10.1016/j.cpletx.2019.100031

Cited by 10 publications

(5 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…65 They reported a larger interaction energy for CH 3 OH⋯NH 3 , inconsistent with the stronger aqueous acidity of CH 3 SH compared to CH 3 OH. Jaju et al calculated the S–H⋯N hydrogen bonding stabilization energy in the [C 5 H 5 –N⋯H–SH] complex to be ∼3 kcal mol-1, which is ∼1 kcal mol −1 larger than the S–H⋯O interaction in the SH 2 ⋯CH 3 OH complex (at the MP2/aug-cc-pVTZ level), 66 perhaps due simply to the higher basicity of the N atom than the O atom. The distances for the S–H⋯N and S–H⋯O hydrogen bonds in these complexes are predicted to be 2.08 Å and 2.10 Å, respectively.…”

Section: Noncovalent Interactions Involving Sulfur Atomsmentioning

confidence: 99%

“…CCSD(T)). 47,53,65,66,77,116,117,[119][120][121]122 For small systems, these methods can be affordable. A study by Rothlisberger and co-workers showed that dispersion corrected atom centered potentials (DCACPs) 123,124 significantly improve the DFT description of the weak interactions of sulfur-containing molecules and the resulting DFT method correctly reproduces MP2 or CCSD(T) binding energies.…”

Section: Recommendations For Modelersmentioning

confidence: 99%

“…120 For basis sets, double-ζ or triple-ζ Pople type basis sets that include diffuse and polarization functions, Weigend's def2-TZVP 125,126 basis set, and Dunning's correlation-consistent cc-pVnZ or augmented correlation-consistent aug-cc-pVnZ (where n = D, T, or Q) basis sets [127][128][129][130][131] are commonly used in calculations on sulfurbased noncovalent interactions. 53,56,[64][65][66]71,77,[115][116][117][119][120][121] To obtain reliable interaction energies, the counterpoise correction for basis set superposition error (BSSE) 132 and corrections for zero-point vibrational energies are recommended, especially when small basis sets are used. [133][134][135] If one wishes to include solvent in one's modelling, there are three general approaches: implicit solvation, explicit sol-Fig.…”

Section: Recommendations For Modelersmentioning

confidence: 99%

See 2 more Smart Citations

Impacts of noncovalent interactions involving sulfur atoms on protein stability, structure, folding, and bioactivity

Kojasoy

Tantillo

2023

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

Section: Noncovalent Interactions Involving Sulfur Atomsmentioning

confidence: 99%

Section: Recommendations For Modelersmentioning

confidence: 99%

Section: Recommendations For Modelersmentioning

confidence: 99%

See 1 more Smart Citation

Impacts of noncovalent interactions involving sulfur atoms on protein stability, structure, folding, and bioactivity

Kojasoy

Tantillo

2023

Org. Biomol. Chem.

View full text Add to dashboard Cite

show abstract

“…These NCIs are crucial for the stability, structure, and function of compounds and proteins containing selenium, as well as for molecular recognition [ 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 ]. Theoretical and experimental studies have demonstrated that selenium can serve as a proton acceptor to engage in D–H ∙∙∙ Se (D = C, N, O, S) hydrogen bonds (HBs) [ 18 , 19 , 20 , 21 , 22 , 23 ] and also act as a proton donor to form Se–H ∙∙∙ A (A = N, O, S, Se, π) HBs [ 24 , 25 , 26 , 27 , 28 ]. These selenium-centered hydrogen bonds (SeCHBs) are a significant class of selenium-containing NCIs.…”

Section: Introductionmentioning

confidence: 99%

Unveiling the Nature and Strength of Selenium-Centered Chalcogen Bonds in Binary Complexes of SeO2 with Oxygen-/Sulfur-Containing Lewis Bases: Insights from Theoretical Calculations

Lu,

Chen,

Liu

et al. 2024

IJMS

View full text Add to dashboard Cite

Among various non-covalent interactions, selenium-centered chalcogen bonds (SeChBs) have garnered considerable attention in recent years as a result of their important contributions to crystal engineering, organocatalysis, molecular recognition, materials science, and biological systems. Herein, we systematically investigated π–hole-type Se∙∙∙O/S ChBs in the binary complexes of SeO2 with a series of O-/S-containing Lewis bases by means of high-level ab initio computations. The results demonstrate that there exists an attractive interaction between the Se atom of SeO2 and the O/S atom of Lewis bases. The interaction energies computed at the MP2/aug-cc-pVTZ level range from −4.68 kcal/mol to −10.83 kcal/mol for the Se∙∙∙O chalcogen-bonded complexes and vary between −3.53 kcal/mol and −13.77 kcal/mol for the Se∙∙∙S chalcogen-bonded complexes. The Se∙∙∙O/S ChBs exhibit a relatively short binding distance in comparison to the sum of the van der Waals radii of two chalcogen atoms. The Se∙∙∙O/S ChBs in all of the studied complexes show significant strength and a closed-shell nature, with a partially covalent character in most cases. Furthermore, the strength of these Se∙∙∙O/S ChBs generally surpasses that of the C/O–H∙∙∙O hydrogen bonds within the same complex. It should be noted that additional C/O–H∙∙∙O interactions have a large effect on the geometric structures and strength of Se∙∙∙O/S ChBs. Two subunits are connected together mainly via the orbital interaction between the lone pair of O/S atoms in the Lewis bases and the BD*(OSe) anti-bonding orbital of SeO2, except for the SeO2∙∙∙HCSOH complex. The electrostatic component emerges as the largest attractive contributor for stabilizing the examined complexes, with significant contributions from induction and dispersion components as well.

show abstract

“…The research on nature of DOI: 10.1002/masy.202000252 selenium hydrogen bonding is emerging in recent time. [9,10] Hypervalent spirocyclic selenium compounds have demonstrated efficient mimetics of selenoenzme glutathione peroxidase (GPx). [11][12][13][14][15][16][17] The aerobic metabolism produces harmful peroxides which are reduced by the catalytic activity of GPx.…”

Section: Introductionmentioning

confidence: 99%

Molecular structure and HOMO/LUMO analysis of 1,1'‐Spirobi[3H‐2,1‐benzoxaselenolene] by quantum chemical investigation

Guin

Verma

Singh

et al. 2021

Macromolecular Symposia

View full text Add to dashboard Cite

This work involves the investigation of equilibrium geometry, electronic energy, the HOMO/LUMO band gap, and Mulliken population analysis of 1,1'‐Spirobi[3H‐2,1‐benzoxaselenolene] using density functional approach. A total of 10 functionals are tested for better prediction of the molecular structure of the title compound. The functional GGA‐BLYP with the DNP basis set is found to be the best to correctly predict the experimental structure. The HOMO‐LUMO electronic gap is found to be 3.849 eV.

show abstract

Electronic substituent effect on Se-H⋯N hydrogen bond: A computational study of para-substituted pyridine-SeH2 complexes

Cited by 10 publications

References 39 publications

Impacts of noncovalent interactions involving sulfur atoms on protein stability, structure, folding, and bioactivity

Impacts of noncovalent interactions involving sulfur atoms on protein stability, structure, folding, and bioactivity

Unveiling the Nature and Strength of Selenium-Centered Chalcogen Bonds in Binary Complexes of SeO2 with Oxygen-/Sulfur-Containing Lewis Bases: Insights from Theoretical Calculations

Molecular structure and HOMO/LUMO analysis of 1,1'‐Spirobi[3H‐2,1‐benzoxaselenolene] by quantum chemical investigation

Contact Info

Product

Resources

About