Tautomeric Equilibria of Substituted 2-Pyridone/2-Hydroxypyridine in the Gas and Aqueous Phases
Chemical Science International Journal · pp. 1–11 · Published 14 Aug 2018
10.9734/CSJI/2018/42946Abstract
Heats of formation, entropies and Gibbs free energies for the twenty structures of substituted 2-pyridone and 2-hydroxypyridine were studied using semiempirical Austin Model (AM1) and Parametric Method 3 (PM3) calculations at the self-consistent field level, both in the gas and liquid phases, with full geometry optimization. It was revealed from the study that 2-hydroxypyridine is predominant in gas phase, while 2-pyridone in the liquid phase which agrees with the experimental and theoretical predictions. All substituents such as F, Cl, OH, CH3, NH2, NO2, CHO, CN, CF3 stabilize the 2-pyridone in the gas and liquid phases except F, Cl and NH2 in PM3 calculations in the gas phase. The substituents stabilization is more effective in liquid phase. This was also confirmed by thermodynamic calculations and isodesmic reactions.
Cited by 4
Doaa Samaha, Sawsan Mahmoud, Mosaad Sayed Mohamed · Journal of Enzyme Inhibition and Medicinal Chemistry · 2024
Doaa Samaha, Sawsan Mahmoud, Mosaad S. Mohamed · 2023
Jason B. Harper, Karin S. Schaffarczyk McHale · Comprehensive Heterocyclic Chemistry IV · 2022
S. Ida, P. Wilson, B. Neppolian · Ultrasonics Sonochemistry · 2020
Related research
- Effect of Substituents on Methylenecyclobutane / 1-Methylcyclobutene System — shares topic coverage
- A DFT Study on Stepwise Fluorinated Methylenecyclopentane ⇌1-Methylcyclopentene System — shares topic coverage
- Reactivity Indices and Theoretical Estimation of Acidity Constants of Diphenylphosphine Oxides in Dichloromethane — shares topic coverage
- Theoretical Study of Stability, Tautomerism, Equilibrium Constants (pKT) of 2-Thiouracil in Gas Phase and Different Solvents (Water and Acetonitrile) by the Density Functional Theory Method — shares topic coverage
- A Theoretical Study of the Enol Contents of Cyclohexanone, Cyclopentanone and Acetone — shares topic coverage
Article metrics
Real usage data collected on this platform.
0
Page views
0
PDF downloads
0
Outbound clicks
4
Citations
Views by country
Approximate, from request IP at view time — not citizenship or institution. Countries with fewer than 5 views are grouped as "Other".
No views recorded yet.
Traffic sources
Referring site, by host.
No traffic recorded yet.
Views and downloads exclude known bots/crawlers. Citations combines this platform's own DOI-resolved index with each external source's own reported total — see Cited by above for individually listed citing works. Last refreshed 0 seconds ago.