Staff Publications

Staff Publications

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    'Staff publications' is the digital repository of Wageningen University & Research

    'Staff publications' contains references to publications authored by Wageningen University staff from 1976 onward.

    Publications authored by the staff of the Research Institutes are available from 1995 onwards.

    Full text documents are added when available. The database is updated daily and currently holds about 240,000 items, of which 72,000 in open access.

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Record number 362539
Title Ureidobenzotriazine Multiple H-Bonding Arrays: The Importance of Geometrical Details on the Stability of H-Bonds
Author(s) Ligthart, G.B.W.L.; Guo, D.; Spek, A.L.; Kooijman, H.; Zuilhof, H.; Sijbesma, R.P.
Source Journal of Organic Chemistry 73 (2008)1. - ISSN 0022-3263 - p. 111 - 117.
Department(s) Laboratory for Organic Chemistry
Publication type Refereed Article in a scientific journal
Publication year 2008
Keyword(s) 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
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.
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