Journal of Molecular Modeling

, Volume 13, Issue 9, pp 951–963

QSPR modeling of hyperpolarizabilities

  • Alan R. Katritzky
  • Liliana Pacureanu
  • Dimitar Dobchev
  • Mati Karelson
Original Paper

DOI: 10.1007/s00894-007-0209-4

Cite this article as:
Katritzky, A.R., Pacureanu, L., Dobchev, D. et al. J Mol Model (2007) 13: 951. doi:10.1007/s00894-007-0209-4

Abstract

The polarizabilities and the first and second hyperpolarizabilities of 219 conjugated organic compounds are modeled by QSPR (quantitative structure activity relationship) based on a large pool of constitutional, topological, electronic and quantum chemical descriptors calculated by CODESSA Pro (comprehensive descriptors for structural and statistical analysis) derived solely from molecular structure. Multilinear models were developed using the BMLR (best multilinear regression) algorithm to relate the experimental (hyper)polarizabilities to their predicted values. The regression equations include AM1 (Austin model 1) calculated (hyper)polarizabilities together with the size, electrostatic and quantum chemical descriptors to compensate for the imprecision of the AM1 computational method. The results emphasize the main factors that influence (hyper)polarizability. All models were validated by the “leave-one-out” method and internal validations that confirmed the stability and good predictive ability.

Figure

Plot of experimental versus predicted second hyperpolarizability values for conjugated aromatic compounds

Keywords

CODESSA Pro Multilinear regression Polarizability QSPR 

Supplementary material

894_2007_209_MOESM1_ESM.doc (505 kb)
Table 1Experimental and predicted (hyper)polarizability values for conjugated organic compounds that display NLO properties are available (DOC 505 kb) (doi:10.1007/s00894-007-0209-4)

Copyright information

© Springer-Verlag 2007

Authors and Affiliations

  • Alan R. Katritzky
    • 1
  • Liliana Pacureanu
    • 1
  • Dimitar Dobchev
    • 1
    • 2
  • Mati Karelson
    • 2
    • 3
  1. 1.Center for Heterocyclic Compounds, Department of ChemistryUniversity of FloridaGainesvilleUSA
  2. 2.Department of ChemistryTallinn University of TechnologyTallinnEstonia
  3. 3.Department of ChemistryUniversity of TartuTartuEstonia

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