Application of quantum chemical descriptor in quantitative structure activity and structure property relationship

Abstract Various quantum chemical descriptors such as ionisation potential (I), electron affinity (A), quantum chemical hardness index (η), softness index (S), electronegativity (χ) and electrophilicity (ω) have been used in order to develop a possible quantitative structure–activity and structure–property relationship (QSAR/QSPR) model for a series of alkanes. The correlation between `I' and boiling point (BP) of alkanes (C2–C8) has been found to be −0.984. Among the six selected descriptors, linear relations derived from `I' reproduce fairly better experimental values for all the selected macroscopic properties. Hardness and softness indices exhibit acceptable correlation for all the selected macroscopic properties. They show promising correlation for heat of formation thereby establishing the fact that hardness is a measure of stability of molecules.

[1]  S. P. Gupta,et al.  QSAR (quantitative structure-activity relationship) studies on local anesthetics , 1991 .

[2]  Corwin Hansch,et al.  A survey of Hammett substituent constants and resonance and field parameters , 1991 .

[3]  C. Ioannides,et al.  A quantitative structure-activity relationship study on a series of 10 para-substituted toluenes binding to cytochrome P4502B4 (CYP2B4), and their hydroxylation rates. , 1995, Biochemical pharmacology.

[4]  R. Parr,et al.  Absolute hardness: companion parameter to absolute electronegativity , 1983 .

[5]  A. Debnath,et al.  International Commission for Protection Against Environmental Mutagens and Carcinogens. The importance of the hydrophobic interaction in the mutagenicity of organic compounds. , 1994, Mutation research.

[6]  Æleen Frisch,et al.  Exploring chemistry with electronic structure methods , 1996 .

[7]  C. Hansch,et al.  Comparative QSAR analysis of estrogen receptor ligands. , 1999, Chemical reviews.

[8]  Robert G. Parr,et al.  New measures of aromaticity: absolute hardness and relative hardness , 1989 .

[9]  R. Parr,et al.  Electronegativity: The density functional viewpoint , 1978 .

[10]  N. L. Allinger.  Calculation of Molecular Structure and Energy by Force-Field Methods , 1976 .

[11]  D. Lewis,et al.  Interaction of a series of nitriles with the alcohol-inducible isoform of P450: computer analysis of structure-activity relationships. , 1994, Xenobiotica; the fate of foreign compounds in biological systems.

[12]  L. Pauling.  The Nature Of The Chemical Bond , 1939 .

[13]  Rainer Franke,et al.  Theoretical drug design methods , 1984 .

[14]  R. Parr,et al.  Principle of maximum hardness , 1991 .

[15]  Robert G. Parr,et al.  Activation hardness: new index for describing the orientation of electrophilic aromatic substitution , 1990 .

[16]  M. Karelson,et al.  Quantum-Chemical Descriptors in QSAR/QSPR Studies. , 1996, Chemical reviews.

[17]  Ralph G. Pearson,et al.  Recent advances in the concept of hard and soft acids and bases , 1987 .

[18]  Satya P. Gupta,et al.  QSAR studies on hallucinogens , 1983 .

[19]  Susumu Shimoda,et al.  QSAR of Fungicidal Δ3‐1,2,4‐Thiadiazolines. Reactivity‐Activity Correlation of SH‐Inhibitors , 1993 .