Prediction of partition coefficients of benzothiophene and benzothiophene 1,1-dioxide in octane/acetonitrile system using COSMO theory

Yusuke Shimoyama, Yoshio Iwai, Satoshi Yoda, Takeshi Furuya

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

The partition coefficients of benzothiophene (BT) and benzothiophene 1,1-dioxide (BTDO) in the octane/ acetonitrile system were predicted using the COSMO (conductor-like screening model) based activity coefficient models COSMO-SAC (segment activity coefficient) and COSMO-UNIQUAC. In COSMO-UNIQUAC, a segment activity coefficient was described in a UNIQUAC-type equation. The results with COSMO-UNIQUAC were compared with those from the COSMO-SAC model. It was found that COSMO-UNIQUAC reproduced the experimental data more accurately than COSMO-SAC. The surface charge density profiles (σ-profiles) of functional groups on BT and BTDO molecules were utilized to determine that the partition coefficients of BTDO are much lower than those of BT. A hypothetical molecule with the volume and surface area of BTDO was conducted by using the σ-profiles of functional groups on BT and BTDO. The partition coefficients of the hypothetical component were predicted by COSMO-UNIQUAC. It was revealed that the partitions of BTDO in the octane/acetonitrile system were influenced from the charge density changes by the oxidation on not only the sulfur atom but also on the carbon and hydrogen atoms.

Original languageEnglish
Pages (from-to)3247-3252
Number of pages6
JournalIndustrial and Engineering Chemistry Research
Volume47
Issue number9
DOIs
Publication statusPublished - May 7 2008

All Science Journal Classification (ASJC) codes

  • Chemistry(all)
  • Chemical Engineering(all)
  • Industrial and Manufacturing Engineering

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