Ureidobenzotriazine Multiple H-Bonding Arrays: The Importance of Geometrical Details on the Stability of H-Bonds

G.B.W.L. Ligthart, D. Guo, A.L. Spek, H. Kooijman, H. Zuilhof, R.P. Sijbesma

Research output: Contribution to journalArticleAcademicpeer-review

16 Citations (Scopus)

Abstract

A 3-ureidobenzo-1,2,4-triazine 1-N-oxide (1) was synthesized successfully. The derivative displays an acceptor-donor-acceptor-acceptor (ADAA) hydrogen-bonding motif in CDCl3 and DMSO-d6 solution as well as in the solid state. Although moderately strong association of 1 was observed with DAD motifs, nonspecific binding is observed with ureidopyridines featuring a complementary DADD array. Density functional calculations of conformations 1a and 1b together with two complexes revealed the clearly nonplanar geometry of the multiply hydrogen-bonded complex, in which some bonds are significantly longer (3.2 Å) than is optimal for H-bonds. As a result, only very small free energies of association were calculated, in line with the experimentally observed absence of specific assembly of the components.
Original languageEnglish
Pages (from-to)111-117
JournalJournal of Organic Chemistry
Volume73
Issue number1
DOIs
Publication statusPublished - 2008

Keywords

  • 3-amino-1,2,4-benzotriazine 1,4-dioxide tirapazamine
  • donor-acceptor interaction
  • pyridine n-oxides
  • hydrogen-bonds
  • heterocyclic ureas
  • molecular recognition
  • guanine-cytosine
  • guanidine base
  • complexes
  • polymers

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