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Structural Chemistry

, Volume 21, Issue 5, pp 955–964 | Cite as

Synthesis and structural characterization of novel 2-benzimidazolylthioureas: adducts of natural isothiocyanates and 2-amino-1-methylbenzimidazole

  • Anna ŚmiechowskaEmail author
  • Witold Przychodzeń
  • Jarosław Chojnacki
  • Piotr Bruździak
  • Jacek Namieśnik
  • Agnieszka Bartoszek
Original Research

Abstract

Adducts of natural allyl, phenethyl, and benzyl isothiocyanates and 2-amino-1-methylbenzimidazole were synthesized. After optimization of the reaction conditions, the target 2-benzimidazolylthioureas were obtained in reasonable yields. The detailed molecular and crystal structures of these compounds were characterized by spectroscopic and X-ray methods. Spectral analysis demonstrated that N-(1-methylbenzimidazolyl)-N′-allylthiourea, N-(1-methylbenzimidazolyl)-N′-benzylthiourea, and N-(1-methylbenzimidazolyl)-N′-phenethylthiourea exist in solution in an unprecedented three tautomeric forms, whose structures were corroborated unambiguously.

Keywords

Thioureas Isothiocyanates 2-Aminobenzimidazole Tautomerism 

Notes

Acknowledgments

The studies were supported by the Polish Ministry of Science and Higher Education, grant No. 312244336 and by the European Union (European Social Fund) within the framework of the project “InnoDoktorant—Scholarships for PhD students, 1st edition.” Calculations were carried out at the Academic Computer Center in Gdansk (TASK).

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Copyright information

© Springer Science+Business Media, LLC 2010

Authors and Affiliations

  • Anna Śmiechowska
    • 1
    Email author
  • Witold Przychodzeń
    • 1
  • Jarosław Chojnacki
    • 1
  • Piotr Bruździak
    • 1
  • Jacek Namieśnik
    • 1
  • Agnieszka Bartoszek
    • 1
  1. 1.Chemical FacultyGdańsk University of TechnologyGdanskPoland

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