TY - JOUR
T1 - Computational study of solvation free energy, dipole moment, polarizability, hyperpolarizability and molecular properties of betulin, a constituent of Corypha taliera (Roxb.)
AU - Khan, Mohammad Firoz
AU - Rashid, Ridwan Bin
AU - Hossain, Md Aslam
AU - Rashid, Mohammad A.
N1 - Funding Information:
One of us (MAR) is thankful to the Ministry of Education, Government of the People's Republic of Bangladesh for a research grant (No. 37.01.0000.078. 02.018.13-125/10/2/2015) for the period 2014-15 to 2016-17 to carry out the work.
Publisher Copyright:
© 2017, University of Dhaka. All rights reserved.
PY - 2017
Y1 - 2017
N2 - Ab initio calculations were carried out to studysolvation free energy, dipole moment, molecular electrostatic potential (MESP), Mulliken charge distribution, polarizability, hyperpolarizability and different molecular properties like global reactivity descriptors (chemical hardness, softness, chemical potential, electronegativity, electrophilicity index) of betulin. B3LYP/6-31G(d,p) level of theory was used to optimize the structure both in gas phase and in solution. The solvation free energy, dipole moment and molecular properties were calculated by applying the Solvation Model on Density (SMD) in six solvent systems namely water, dimethyl sulfoxide (DMSO), acetonitrile, n-octanol, chloroform and carbontetrachloride. The solvation free energy of betulin increases with decreasing polarity of the solvent. No systematic trend of hyperpolarizability with solvent polarity is found. Molecular electrostatic potential (MESP) and Mulliken population analysis (MPA) reveal that the most possible sites for nucleophilic attack are C30, H76 and H77 and electrophilic attack are O1 and O2 among the atoms in betulin. However, the dipole moment, polarizability, chemical potential, electronegativity and electrophilicity index of betulin increase on going from non-polar to polar solvents. Chemical hardness was also increased with decreasing polarity of the solvent and opposite relation was found in the case of softness. These results provide better understanding of the stability and reactivity of betulin in different solvent systems.
AB - Ab initio calculations were carried out to studysolvation free energy, dipole moment, molecular electrostatic potential (MESP), Mulliken charge distribution, polarizability, hyperpolarizability and different molecular properties like global reactivity descriptors (chemical hardness, softness, chemical potential, electronegativity, electrophilicity index) of betulin. B3LYP/6-31G(d,p) level of theory was used to optimize the structure both in gas phase and in solution. The solvation free energy, dipole moment and molecular properties were calculated by applying the Solvation Model on Density (SMD) in six solvent systems namely water, dimethyl sulfoxide (DMSO), acetonitrile, n-octanol, chloroform and carbontetrachloride. The solvation free energy of betulin increases with decreasing polarity of the solvent. No systematic trend of hyperpolarizability with solvent polarity is found. Molecular electrostatic potential (MESP) and Mulliken population analysis (MPA) reveal that the most possible sites for nucleophilic attack are C30, H76 and H77 and electrophilic attack are O1 and O2 among the atoms in betulin. However, the dipole moment, polarizability, chemical potential, electronegativity and electrophilicity index of betulin increase on going from non-polar to polar solvents. Chemical hardness was also increased with decreasing polarity of the solvent and opposite relation was found in the case of softness. These results provide better understanding of the stability and reactivity of betulin in different solvent systems.
KW - Betulin
KW - Dipole moment
KW - Polarizability
KW - Solvation free energy
KW - Solvation model
UR - http://www.scopus.com/inward/record.url?scp=85026640918&partnerID=8YFLogxK
U2 - 10.3329/dujps.v16i1.33376
DO - 10.3329/dujps.v16i1.33376
M3 - Article
AN - SCOPUS:85026640918
SN - 1816-1820
VL - 16
SP - 1
EP - 9
JO - Dhaka University Journal of Pharmaceutical Sciences
JF - Dhaka University Journal of Pharmaceutical Sciences
IS - 1
ER -