Jump to main content
Jump to site search
Publishing
Advanced

Issue 11, 2011
Previous Article Next Article

A bis-urea naphthalene macrocycle displaying two crystal structures with parallel ureas

Michael F. Geer,a  Mark D. Smitha  and  Linda S. Shimizu*a 
Author affiliations

* Corresponding authors

a University of South Carolina, Department of Chemistry and Biochemistry, Columbia, USA
E-mail: shimizul@chem.sc.edu
Fax: +803-777-9521
Tel: +803-777-2066

Abstract

Herein we synthesized a bis-urea macrocycle from 2,7-dimethylnaphthalene that displays an unusual parallel urea conformation. The naphthalenes also adopt a bowl shape over the anticipated parallel planar orientation. Crystallization of the macrocycle from different solvent systems affords two solvated forms. 1·DMSO·(H2O)2 has an extended columnar structure where parallel macrocycles are linked by intervening hydrogen bonded water molecules. In 1·(MeOH)2 direct hydrogen-bonds link the macrocycles into chains, which hydrogen-bond with methanol molecules to form a layered structure.

Graphical abstract: A bis-urea naphthalene macrocycle displaying two crystal structures with parallel ureas

Back to tab navigation
Download options Please wait...

Supplementary files

Publication details

The article was received on 16 Feb 2011, accepted on 02 Apr 2011 and first published on 15 Apr 2011


Article type: Communication
DOI: 10.1039/C1CE05207A
Citation: CrystEngComm, 2011,13, 3665-3669
  •   Request permissions

    A bis-urea naphthalene macrocycle displaying two crystal structures with parallel ureas

    M. F. Geer, M. D. Smith and L. S. Shimizu, CrystEngComm, 2011, 13, 3665
    DOI: 10.1039/C1CE05207A

    If you are not the author of this article and you wish to reproduce material from it in a third party non-RSC publication you must formally request permission using RightsLink. Go to our Instructions for using RightsLink page for details.

    Authors contributing to RSC publications (journal articles, books or book chapters) do not need to formally request permission to reproduce material contained in this article provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      Reproduced from Ref. XX with permission from the Centre National de la Recherche Scientifique (CNRS) and The Royal Society of Chemistry.
    • For reproduction of material from PCCP:
      Reproduced from Ref. XX with permission from the PCCP Owner Societies.
    • For reproduction of material from PPS:
      Reproduced from Ref. XX with permission from the European Society for Photobiology, the European Photochemistry Association, and The Royal Society of Chemistry.
    • For reproduction of material from all other RSC journals and books:
      Reproduced from Ref. XX with permission from The Royal Society of Chemistry.

    If the material has been adapted instead of reproduced from the original RSC publication "Reproduced from" can be substituted with "Adapted from".

    In all cases the Ref. XX is the XXth reference in the list of references.

    If you are the author of this article you do not need to formally request permission to reproduce figures, diagrams etc. contained in this article in third party publications or in a thesis or dissertation provided that the correct acknowledgement is given with the reproduced material.

    Reproduced material should be attributed as follows:

    • For reproduction of material from NJC:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the Centre National de la Recherche Scientifique (CNRS) and the RSC
    • For reproduction of material from PCCP:
      [Original citation] - Reproduced by permission of the PCCP Owner Societies
    • For reproduction of material from PPS:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry (RSC) on behalf of the European Society for Photobiology, the European Photochemistry Association, and RSC
    • For reproduction of material from all other RSC journals:
      [Original citation] - Reproduced by permission of The Royal Society of Chemistry

    If you are the author of this article you still need to obtain permission to reproduce the whole article in a third party publication with the exception of reproduction of the whole article in a thesis or dissertation.

    Information about reproducing material from RSC articles with different licences is available on our Permission Requests page.

Search articles by author

Spotlight

Advertisements