Theoretical study of thermochemical and structural parameters of chlorinated isomers of aniline

Ibrahem Altarawneh, Khaled Altarawneh, Ala'a H. Al-Muhtaseb, Saleh Alrawadieh, Mohammednoor Altarawneh

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

Thermochemical parameters, in terms of standard enthalpies of formation, standard entropies and Gibbs free energies of formation and heat capacities are calculated herein for all chlorinated isomers of aniline. Calculated values of standard enthalpies of formation are in agreement with the available experimental values. Calculated values of solvation energies indicate that the interaction of chlorinated aniline with water molecules decreases with the degree of chlorination. Trends in angles and barriers of inversion indicate that the pyramidalisation in chlorinated aniline decreases with the degree of chlorination. The most stable isomer in each homologue group is highlighted. Interaction of ortho chlorine atoms with the electron donating group of amine affords ortho-substituted isomers slight stability over other isomers.

Original languageEnglish
Pages (from-to)30-35
Number of pages6
JournalComputational and Theoretical Chemistry
Volume985
DOIs
Publication statusPublished - Apr 1 2012

Fingerprint

aniline
Isomers
Theoretical Models
isomers
Halogenation
chlorination
Chlorination
Enthalpy
enthalpy
Chlorine
Entropy
Amines
Solvation
energy of formation
Gibbs free energy
Hot Temperature
Electrons
Specific heat
chlorine
solvation

Keywords

  • Chlorinated anilines
  • DFT
  • Inversion
  • Solvation energies

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Biochemistry
  • Condensed Matter Physics

Cite this

Theoretical study of thermochemical and structural parameters of chlorinated isomers of aniline. / Altarawneh, Ibrahem; Altarawneh, Khaled; Al-Muhtaseb, Ala'a H.; Alrawadieh, Saleh; Altarawneh, Mohammednoor.

In: Computational and Theoretical Chemistry, Vol. 985, 01.04.2012, p. 30-35.

Research output: Contribution to journalArticle

Altarawneh, Ibrahem ; Altarawneh, Khaled ; Al-Muhtaseb, Ala'a H. ; Alrawadieh, Saleh ; Altarawneh, Mohammednoor. / Theoretical study of thermochemical and structural parameters of chlorinated isomers of aniline. In: Computational and Theoretical Chemistry. 2012 ; Vol. 985. pp. 30-35.
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AB - Thermochemical parameters, in terms of standard enthalpies of formation, standard entropies and Gibbs free energies of formation and heat capacities are calculated herein for all chlorinated isomers of aniline. Calculated values of standard enthalpies of formation are in agreement with the available experimental values. Calculated values of solvation energies indicate that the interaction of chlorinated aniline with water molecules decreases with the degree of chlorination. Trends in angles and barriers of inversion indicate that the pyramidalisation in chlorinated aniline decreases with the degree of chlorination. The most stable isomer in each homologue group is highlighted. Interaction of ortho chlorine atoms with the electron donating group of amine affords ortho-substituted isomers slight stability over other isomers.

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