Hydrogen bonded complexes of oxazole family: electronic structure, stability, and reactivity aspects

Chopra, Neha; Kaur, Deepinder; Chopra, Geetanjali

doi:10.1007/s11224-017-1032-x

Cited by 8 publications

(2 citation statements)

References 36 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Among several biological active compounds, azines serve as a key building block for proteins, nucleotides, and polymers that play a pivotal role in biological and material science application. Hydrogen bonding involved in these species has reaped much more potential in medicinal chemistry, − and recently, several theoretical studies have been performed to analyze the effect of successive addition of nitrogen atoms in the biologically active heterocyclic aromatic moieties. − Azines are interesting model systems for investigating how successive replacement of C–H group with nitrogen atom affects the hydrogen-bonding ability of a 6-membered aromatic ring. Pyridine is found to have a large number of biological activities, including antiviral, anticancer, antimicrobial, antidiabetic, antitubercular, antidote, antileishmanial, antioxidant, antichagasic, antithrombin, anticoagulant, etc.…”

Section: Introductionmentioning

confidence: 99%

Exploring the Role of Consecutive Addition of Nitrogen Atoms on Stability and Reactivity of Hydrogen-Bonded Azine–Water Complexes

Chopra

Kaur

2019

ACS Omega

Self Cite

View full text Add to dashboard Cite

The second-order Møller–Plesset perturbation theory (MP2) and density functional theory with dispersion function calculations have been applied to investigate the hydrogen-bonding interaction between azines and water. The study suggests that the ability of nitrogen present in azine to act as a hydrogen-bond acceptor decreases in the order of pyridine ( PY ) > diazine ( DZ ) > triazine ( TZ ) > tetrazine ( TTZ ) > pentazine ( PZ ) > hexazine ( HZ ). Natural bond orbital (NBO) analysis, atoms in molecules, symmetry-adapted perturbation theory (SAPT), and molecular electrostatic potential studies reflect the factors important for hydrogen-bond strength as well as for the structural, electronic, and vibrational changes occurring during complexation. NBO analysis reflects that upon gradual addition of nitrogen atoms, hyperconjugation leads to an increase in the population of antibonding O–H bond, thus causing elongation and weakening of O–H bond in complexes incorporating N···H–O W interaction, whereas rehybridization leads to an increase in the s character of the carbon hybrid orbital in C–H bond, thus causing contraction and shortening of C–H bond in complexes having C–H···O W interactions. From the topological analysis, an excellent linear correlation is found to exist between stabilization energy (Δ E BSSE ), electron density (ρ c ), and its Laplacian (∇ 2 ρ c ) at the bond critical points.

show abstract

Section: Introductionmentioning

confidence: 99%

Exploring the Role of Consecutive Addition of Nitrogen Atoms on Stability and Reactivity of Hydrogen-Bonded Azine–Water Complexes

Chopra

Kaur

2019

ACS Omega

Self Cite

View full text Add to dashboard Cite

show abstract

“…Recent findings suggest that the biological effects of hydrogen peroxide (HP) are actually mediated by hydrogen-bonded complexes of HP and molecules of biological interest. In the last decade, several studies − had been conducted to describe the energetic and structural properties of hydrogen-bonded complexes of azoles.…”

Section: Introductionmentioning

confidence: 99%

Nature and Hierarchy of Hydrogen-Bonding Interactions in Binary Complexes of Azoles with Water and Hydrogen Peroxide

2018

Self Cite

View full text Add to dashboard Cite

In the present study, the hydrogen-bonded complexes of azole with water and hydrogen peroxide are systematically investigated by second-order Møller–Plesset perturbation theory and density functional theory with dispersion function calculations. This study suggests that the ability of pyrrolic nitrogen (NH) atom to function as hydrogen-bond donor increases with the introduction of nitrogen atoms in the ring, whereas the ability of pyridinic nitrogen (N) atom to act as hydrogen-bond acceptor reduces with successive aza substitution in the ring. With introduction of nitrogen atoms in the ring, the vibrational frequency, stabilization energy, and electron density in the σ antibonding orbitals of the X–H (X = N, C of azole) bond of the complexes all increase or decrease systematically. Decomposition analysis of total stabilization energy showed that the electrostatic energy term is a dominant attractive contribution in comparison to induction and dispersion terms in all of the complexes under study.

show abstract

A computational investigation on the adsorption behavior of bromoacetone on B36 borophene nanosheets

Taier,

Allal,

Bousba

et al. 2024

J Comput Electron

View full text Add to dashboard Cite

Hydrogen bonded complexes of oxazole family: electronic structure, stability, and reactivity aspects

Cited by 8 publications

References 36 publications

Exploring the Role of Consecutive Addition of Nitrogen Atoms on Stability and Reactivity of Hydrogen-Bonded Azine–Water Complexes

Exploring the Role of Consecutive Addition of Nitrogen Atoms on Stability and Reactivity of Hydrogen-Bonded Azine–Water Complexes

Nature and Hierarchy of Hydrogen-Bonding Interactions in Binary Complexes of Azoles with Water and Hydrogen Peroxide

A computational investigation on the adsorption behavior of bromoacetone on B36 borophene nanosheets

Contact Info

Product

Resources

About