Journal of Chemical Crystallography

, Volume 35, Issue 9, pp 723–729

Hydrogen bonding in aromatic formamides

  • Matthias Zeller
  • Robert J. Wilcox
  • Floyd G. SnyderIII
  • Harry A. SeibelII
  • Nathan J. Takas
  • Allen D. Hunter
Article

The solid state structures of two p-substituted aromatic formamides have been determined. p-Nitro formamido benzene (1) crystallizes in the monoclinic space group C2/c with a = 10.9859(7), b = 10.0576(7), c = 13.0331(9) Å, β = 97.148(1) and Z = 8. p-formamido anisole (2) crystallizes in the orthorhombic space group Pna21 with a = 10.5598(7), b = 7.6553(5), c = 9.2522(6) Å and Z = 4. Both compounds show hydrogen bonding in the solid state, forming infinite chains via N–H⋅ < eqid1 > ⋅O = C bridges. For the anisole formamide (2), the molecules exhibit in a zig-zag arrangement. The nitro compound (1) exhibits a spiral-like wavy line with a fourfold repeating unit, making it the first formamide having a chiral N–H⋅ < eqid2 > ⋅O bridged chain reminiscent of those found for α-helices in proteins. While the individual spirals of 1 are orientated either clockwise or counterclockwise, their orientation towards each other is random.

Key words

Formamides hydrogen bonding disorder infinite chain spiral disorder 

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

References

  1. 1.
    (a) Dobson, C.M.; ali, A.; Karplus, M. Angew. Chem., Int. Ed. 1998, 37, 868–893. (b) Dill, K.A. Biochemistry 1990, 29, 7133–7155; (c) Accounts of Chemical Research, 1998, 31(11), entire issue.Google Scholar
  2. 2.
    van der Vaart, A.; Bursulaya, B.D.; Brooks, C.L., III; Merz, K.M., Jr. J. Phys. Chem. B 2000, 194, 9554.CrossRefGoogle Scholar
  3. 3.
    Vendruscolo, M.; Domany, E. J. Chem. Phys. 1998, 109, 11101–11108.CrossRefGoogle Scholar
  4. 4.
    Suhai, S. J. Phys. Chem. 1996, 100, 3950–3958.CrossRefGoogle Scholar
  5. 5.
    Kobko, N.; Paraskevas, L.; del Rio, E.; Dannenberg, J.J. J. Am. Chem. Soc. 2001, 123, 4348.CrossRefPubMedGoogle Scholar
  6. 6.
    (a) Ladell, J.; Post, B. Acta Cryst. 1954, 7, 559. (b) Torrie, B.H.; O’Donovan, C.; Powell, B.M. Molecular Physics 1994, 82(4), 643–649.Google Scholar
  7. 7.
    Conquest Version 1.5, Copyright CCDC 2002. Databases used: CSD version 5.24 (November 2002) + Updates Feb, Apr and Jul 2003.Google Scholar
  8. 8.
    Stryer, L. Biochemistry; 4th edn; W. H. Freeman and Company: New York, 1995, p. 28–32.Google Scholar
  9. 9.
    Bruker (1997). SAINT (Version 6.02), SMART for WNT/2000 (Version 5.625) and SHELXTL. Bruker AXS Inc., Madison, Wisconsin, USA.Google Scholar

Copyright information

© Springer Science + Business Media, Inc. 2005

Authors and Affiliations

  • Matthias Zeller
    • 1
  • Robert J. Wilcox
    • 1
  • Floyd G. SnyderIII
    • 1
  • Harry A. SeibelII
    • 1
  • Nathan J. Takas
    • 1
  • Allen D. Hunter
    • 1
  1. 1.Department of ChemistryYoungstown State UniversityYoungstownUSA

Personalised recommendations