A theoretical study of substituted 2-pyridone2-hydroxypyridine tautomerism

Other Title(s)

دراسة نظرية لنظام 2-بيريدون و 2-هيدروكسي بيريدين المعوض

Dissertant

al-Sabayilah, Ahmad Ali Salim

Thesis advisor

al-Umari, Hamzah

Comitee Members

al-Qudah, Muhammad Mustafa
al-Ashram, Muhammad Hasan
Qasir, Arab Khalil

University

Mutah University

Faculty

Faculty of Science

Department

Department of Chemistry

University Country

Jordan

Degree

Master

Degree Date

2007

English Abstract

All of the possible substitution positions on 2-Pyridone and hydroxypyridine were studied by the use of OH, CH3, CF3, F, NH2, NO2, and CHO substituents, and it is found that position 4 gives the most stable substituted compound.

Also, the effect of substituents (OH, CH3, CF3, F, NH2, NO2, and CHO) on the relative stability of 2-pyridone and 2-hydroxypyridine have been studied.

It is found that 2-pyridone is more stable than 2-hydroxypyridine by 3.117 kcal / mol, and the free energy ΔG was found to be 1.920 kcal / mol, which suggests that the tautomerization is shifted towards the keto form.

The MNDO program and MINDO-Forces was used to estimate optimized geometries, heat of formation, entropies, electron density and dipole moments for all of the substituted and substituted keto and enol compounds.

It is found that the bond lengths, bond angles and dipole moments are affected by the substituents especially at the position where the substituents are attached (position 4).

Also, the stabilizing effect of the substituents on the 2-pyridone and 2-hydroxypyridine were determined by Gibbs free energy (ΔG) and the isoseismic reactions.

All of the substituents studied were found not to effect the position of equilibrium.

The substituents OH, F, NH2 and CH3 were found to be electron releasing groups, where, NO2, CF3 and CHO were electron withdrawing groups.

Main Subjects

Chemistry

Topics

• Spectrometers
• Optics
• Light
• Analytical chemistry
• Absorption spectra

No. of Pages

64

Table of Contents

• APA
• MLA
• AMA

Language

English

Data Type

Arab Theses

Record ID

BIM-304605