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Zeitschrift für Kristallographie - Crystalline Materials

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Volume 230, Issue 6

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Crystal and molecular structures of two 1H-2-substituted benzimidazoles

Pilar Cabildo
  • Fac. de Ciencias, Dpto. Química Orgánica y Bio-Orgánica, Universidad Nacional de Educación a Distancia (UNED), Senda del Rey 9, E-28040 Madrid, Spain
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
/ Rosa M. Claramunt
  • Fac. de Ciencias, Dpto. Química Orgánica y Bio-Orgánica, Universidad Nacional de Educación a Distancia (UNED), Senda del Rey 9, E-28040 Madrid, Spain
  • Other articles by this author:
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/ Fco. Javier Zuñiga
  • Corresponding author
  • Fac. Ciencia y Tecnología, Dpto. Física Materia Condensada, Universidad del Pais Vasco, APDO. 644, 48080 Bilbao, Spain
  • Email
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/ Ibon Alkorta
  • Instituto de Química Médica, Centro de Química Orgánica Manuel Lora-Tamayo, CSIC, Juan de la Cierva 3, E-28006 Madrid, Spain
  • Other articles by this author:
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/ Jose Elguero
  • Instituto de Química Médica, Centro de Química Orgánica Manuel Lora-Tamayo, CSIC, Juan de la Cierva 3, E-28006 Madrid, Spain
  • Other articles by this author:
  • De Gruyter OnlineGoogle Scholar
Published Online: 2015-03-28 | DOI: https://doi.org/10.1515/zkri-2015-0004

Abstract

The X-ray molecular structure of two benzimidazoles unsubstituted on the nitrogen atoms (2-ethyl-1H-benzimidazole and 2-propyl-1H-benzimidazole) has been determined and analysed in the context of crystallographic and solid-state NMR data of seven substituted benzimidazoles. The first compound presents polymorphism, and two polymorphs [forms 3a and 3c] were obtained from different solutions of dichloromethane/hexane. Polymorph (3a) contains two independent molecules differing in the conformation of the ethyl group. Polymorph (3c) contains only one molecule in the asymmetric unit, with similar configuration as the ordered molecule of polymorph (3a). Another polymorphic form (3b) is obtained by cooling form (3a) below 179 K. The transition is related to an order-disorder process and involves a change in the hydrogen-bonding scheme. The second compound (4) presents enantiomorphism and its asymmetric unit contains four independent molecules that differ in the conformation of the 2-propyl group. For form (3a), the splitting of NMR signals is almost perfectly consistent with the features of the crystal structure, whereas not splitting is observed for compound (4). Agreements between NMR and X-ray crystallography techniques are also observed in other simple 2-R-1H-benzimidazoles (R = C4H9, CH2C6H5 and C6H5), but disagreements are found for R = H, CH3.

This article offers supplementary material which is provided at the end of the article.

Keywords: benzimidazoles; low-temperature structure; NMR crystallography; phase transitions; Polymorphism

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About the article

Corresponding author: Fco. Javier Zuñiga, Fac. Ciencia y Tecnología, Dpto. Física Materia Condensada, Universidad del Pais Vasco, APDO. 644, 48080 Bilbao, Spain, E-mail:


Received: 2014-11-19

Accepted: 2015-02-23

Published Online: 2015-03-28

Published in Print: 2015-06-01


Citation Information: Zeitschrift für Kristallographie - Crystalline Materials, Volume 230, Issue 6, Pages 427–438, ISSN (Online) 2196-7105, ISSN (Print) 2194-4946, DOI: https://doi.org/10.1515/zkri-2015-0004.

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