Elucidation of specific aspects of dielectric constants of conjugated organic compounds: A QSPR approach

Areum Lee, Daejin Kim, Kyung Hyun Kim, Seung Hoon Choi, Kihang Choi, Dong Hyun Jung

    Research output: Contribution to journalArticlepeer-review

    10 Citations (Scopus)

    Abstract

    The characteristic aspects of dielectric constants of π-conjugated compounds are elucidated by a quantitative structure property relationship (QSPR) study. To develop a QSPR model, among 141 collected π-conjugated compounds, a subset of 116 compounds was used as the training set for the model building and the rest was used as the test set for the model validation. Statistical regression models using 396 molecular descriptors were generated based on the genetic function approximation algorithm. The predicted dielectric constants obtained by the best model are highly correlated with the experimental values (squared correlation coefficient R 2 of 0.93 and 0.97 for the training and test sets, respectively), while a previous prediction model for general organic molecules (Sild S, Karelson M (2002) J Chem Inf Comput Sci 42:360-367) is not valid for our collected π-conjugated organic compounds. It has been known that the dielectric constants of organic materials are largely influenced by orientational correlations of the constituent molecules. In general, hydrogen bonding is one of the most important intermolecular interactions affecting orientational correlation. In the case of π-conjugated compounds, however, π-π interaction could be another comparable interaction with the hydrogen bonding.

    Original languageEnglish
    Pages (from-to)251-256
    Number of pages6
    JournalJournal of Molecular Modeling
    Volume18
    Issue number1
    DOIs
    Publication statusPublished - 2012 Jan

    Bibliographical note

    Funding Information:
    This study was supported by grant No. 10031803 from the Industrial Source Technology Development Programs funded by the Ministry of Knowledge Economy, Republic of Korea. We thank Accelrys Korea for support with the modeling software.

    Keywords

    • Conjugated organic compound
    • Dielectric constant
    • Orientational correlation
    • Prediction model
    • QSPR

    ASJC Scopus subject areas

    • Catalysis
    • Computer Science Applications
    • Physical and Theoretical Chemistry
    • Organic Chemistry
    • Inorganic Chemistry
    • Computational Theory and Mathematics

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