TY - JOUR
T1 - Theoretical study of thermochemical and structural parameters of chlorinated isomers of aniline
AU - Altarawneh, Ibrahem
AU - Altarawneh, Khaled
AU - Al-Muhtaseb, Ala'a H.
AU - Alrawadieh, Saleh
AU - Altarawneh, Mohammednoor
N1 - Funding Information:
This study has been supported by a grant of computing time from the National Computational Infrastructure (NCI), Australia.
PY - 2012/4/1
Y1 - 2012/4/1
N2 - 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.
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.
KW - Chlorinated anilines
KW - DFT
KW - Inversion
KW - Solvation energies
UR - http://www.scopus.com/inward/record.url?scp=84858159284&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84858159284&partnerID=8YFLogxK
U2 - 10.1016/j.comptc.2012.01.032
DO - 10.1016/j.comptc.2012.01.032
M3 - Article
AN - SCOPUS:84858159284
SN - 2210-271X
VL - 985
SP - 30
EP - 35
JO - Computational and Theoretical Chemistry
JF - Computational and Theoretical Chemistry
ER -