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Unique charge-separated intermolecular and eight-membered intramolecular H-bonds in bis-(thio)barbiturates

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Abstract

Reaction of symmetrical and unsymmetrical (thio)barbituric acids with aldehydes in the presence of triethylamine afforded a new form of bis-(thio)barbiturate containing charge-separated inter- and eight-membered intramolecular H-bonds. The reaction products were obtained as bis-(thio)barbiturates containing eight-membered intramolecular H-bond in the presence of l-(+)-tartaric acid (TA). The intramolecular H-bond strength (kcal/mol) and corresponding pKa value for 4ab′ were estimated to be 37 kcal/mol and −1.3, respectively.

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Acknowledgments

We gratefully acknowledge the financial support by the Research Council of Urmia University.

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Urmia University, 57159, Urmia, Iran

    Nader Noroozi Pesyan

  2. Department of Chemistry, Faculty of Science, Islamic Azad University, Ahar Branch, Ahar, Iran

    Mohammad Jalilzadeh

  3. Department of Chemistry, Faculty of Science, Tabriz Payam-e-noor University, Tabriz, Iran

    Nasim Yalabi Torkaman

  4. Department of Chemistry, Faculty of Science, Atatürk University, 25240, Erzurum, Turkey

    Ertan Şahin

Authors
  1. Nader Noroozi Pesyan
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Corresponding author

Correspondence to Nader Noroozi Pesyan.

Electronic supplementary material

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13738_2013_273_MOESM1_ESM.pdf

Full characterization data for compounds 3cd′–3fd′, 4ab′–4ae′ and crystallographic data for 4ab′ are available (PDF 7154 kb)

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Pesyan, N.N., Jalilzadeh, M., Torkaman, N.Y. et al. Unique charge-separated intermolecular and eight-membered intramolecular H-bonds in bis-(thio)barbiturates. J IRAN CHEM SOC 11, 35–45 (2014). https://doi.org/10.1007/s13738-013-0273-x

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  • DOI: https://doi.org/10.1007/s13738-013-0273-x

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