The DOI matches its Crossref record; 14 of the 14 references it cites were found in a registry or an index.
Stability and Lifetime of Quadruply Hydrogen Bonded 2-Ureido-4[1 H]-pyrimidinone Dimers
Abstract
2-Ureido-4[1 H ]-pyrimidinones are known to dimerize via a strong quadruple hydrogen bond array. A detailed study of the dimerization constant and lifetime of the dimer is presented here. Excimer fluorescence of pyrene-labeled 2-ureido-4[1 H ]-pyrimidinone 1b was used to determine a dimerization constant K dim of 6 × 10 7 M - 1 in CHCl 3, 1 × 10 7 M - 1 in chloroform saturated with water, and 6 × 10 8 M - 1 in toluene (all at 298 K). Under these conditions, the preexchange lifetime of the similar dimers of both 1d and 1e is 170 ms in CDCl 3, 80 ms in wet CDCl 3, and 1.7 s in toluene- d 8, as determined by dynamic NMR spectroscopy. Association rate constants were calculated from the K dim values and the preexchange lifetimes. The resulting values are significantly lower than the diffusion-controlled association rate constants calculated using the Stokes−Einstein and the Debeije equations. This difference is ascribed to a tautomeric equilibrium of the monomer between the dimerizing 4[1 H ]-pyrimidinone and nondimerizing 6[1 H ]-pyrimidinone tautomers, which is unfavorable for dimerization.
Overview
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Integrity signals
Registry
Cites
Statistics
Verification
Claims the paper makes
The claims and statistics of this paper haven’t been checked yet.
Run the check — free, no account needed. It reads the open-access text and checks the sources it cites.
Self-check
Percentages, sums and reported differences re-computed from the paper’s own numbers.
The self-check needs the paper’s full text.
Citations
Cites
Supramolecular Chemistry: Concepts and Perspectives
Lehn, J. (1995) · Wiley eBooks · doi:10.1002/3527607439 · Cited by 9,864
Investigation of exchange processes by two-dimensional NMR spectroscopy
Jeener, J., Meier, B. H., Bachmann, P., & Ernst, R. R. (1979) · The Journal of Chemical Physics · doi:10.1063/1.438208 · Cited by 4,749
Reversible Polymers Formed from Self-Complementary Monomers Using Quadruple Hydrogen Bonding
Sijbesma, R. P., Beijer, F. H., Brunsveld, L., Folmer, B. J. B., Hirschberg, J. H. K. K., Lange, R. F. M., Lowe, J. K. L., & Meijer, E. W. (1997) · Science · doi:10.1126/science.278.5343.1601 · Cited by 2,393
Self-citationStrong Dimerization of Ureidopyrimidones via Quadruple Hydrogen Bonding
Beijer, F. H., Sijbesma, R. P., Kooijman, H., Spek, A. L., & Meijer, E. W. (1998) · Journal of the American Chemical Society · doi:10.1021/ja974112a · Cited by 815
Self-citationApplication of two-dimensional NMR to kinetics of chemical exchange
Perrin, C. L., & Dwyer, T. J. (1990) · Chemical Reviews · doi:10.1021/cr00104a002 · Cited by 753
Dynamics of reversible networks
Leibler, L., Rubinstein, M., & Colby, R. H. (1991) · Macromolecules · doi:10.1021/ma00016a034 · Cited by 724
Stott, K., Stonehouse, J., Keeler, J., Hwang, T.-L., & Shaka, A. J. (1995) · Journal of the American Chemical Society · doi:10.1021/ja00119a048 · Cited by 703
One-Dimensional NOE Experiments Using Pulsed Field Gradients
Stott, K., Keeler, J., Van, Q. N., & Shaka, A. J. (1997) · Journal of Magnetic Resonance · doi:10.1006/jmre.1997.1110 · Cited by 414
Self-Complementarity Achieved through Quadruple Hydrogen Bonding
Beijer, F. H., Kooijman, H., Spek, A. L., Sijbesma, R. P., & Meijer, E. W. (1998) · Angewandte Chemie International Edition · doi:10.1002/(sici)1521-3773(19980202)37:1/2<75::aid-anie75>3.0.co;2-r · Cited by 320
Self-citationStonehouse, J., Adell, P., Keeler, J., & Shaka, A. J. (1994) · Journal of the American Chemical Society · doi:10.1021/ja00092a092 · Cited by 269
Cited by
Using the dynamic bond to access macroscopically responsive structurally dynamic polymers
Wojtecki, R. J., Meador, M. A., & Rowan, S. J. (2011) · Nature Materials · doi:10.1038/nmat2891 · Cited by 1,636
Stimuli-responsive supramolecular polymeric materials
Yan, X., Wang, F., Zheng, B., & Huang, F. (2012) · Chemical Society Reviews · doi:10.1039/c2cs35091b · Cited by 1,631
G‐Quartets 40 Years Later: From 5′‐GMP to Molecular Biology and Supramolecular Chemistry
Davis, J. T. (2004) · Angewandte Chemie International Edition · doi:10.1002/anie.200300589 · Cited by 1,626
Self-healing polymeric materials
Yang, Y., & Urban, M. W. (2013) · Chemical Society Reviews · doi:10.1039/c3cs60109a · Cited by 1,444
Supramolecular polymeric hydrogels
Appel, E. A., del Barrio, J., Loh, X. J., & Scherman, O. A. (2012) · Chemical Society Reviews · doi:10.1039/c2cs35264h · Cited by 1,159
Burattini, S., Greenland, B. W., Merino, D. H., Weng, W., Seppala, J., Colquhoun, H. M., Hayes, W., Mackay, M. E., Hamley, I. W., & Rowan, S. J. (2010) · Journal of the American Chemical Society · doi:10.1021/ja104446r · Cited by 935
Self-Healing Injectable Hydrogels for Tissue Regeneration
Bertsch, P., Diba, M., Mooney, D. J., & Leeuwenburgh, S. C. G. (2023) · Chemical Reviews · doi:10.1021/acs.chemrev.2c00179 · Cited by 892
Yan, X., Liu, Z., Zhang, Q., Lopez, J., Wang, H., Wu, H.-C., Niu, S., Yan, H., Wang, S., Lei, T., et al. (2018) · Journal of the American Chemical Society · doi:10.1021/jacs.8b01682 · Cited by 632
Tough Stimuli-Responsive Supramolecular Hydrogels with Hydrogen-Bonding Network Junctions
Guo, M., Pitet, L. M., Wyss, H. M., Vos, M., Dankers, P. Y. W., & Meijer, E. W. (2014) · Journal of the American Chemical Society · doi:10.1021/ja500205v · Cited by 627
Self-citationChemical and physical aspects of self-healing materials
Yang, Y., Ding, X., & Urban, M. W. (2015) · Progress in Polymer Science · doi:10.1016/j.progpolymsci.2015.06.001 · Cited by 536
A modular and supramolecular approach to bioactive scaffolds for tissue engineering
Dankers, P. Y. W., Harmsen, M. C., Brouwer, L. A., Van Luyn, M. J. A., & Meijer, E. W. (2005) · Nature Materials · doi:10.1038/nmat1418 · Cited by 455
Self-citationChen, J., Gao, Y., Shi, L., Yu, W., Sun, Z., Zhou, Y., Liu, S., Mao, H., Zhang, D., Lu, T., et al. (2022) · Nature Communications · doi:10.1038/s41467-022-32517-4 · Cited by 325
Self‐Healing Supramolecular Block Copolymers
Hentschel, J., Kushner, A. M., Ziller, J., & Guan, Z. (2012) · Angewandte Chemie International Edition · doi:10.1002/anie.201204840 · Cited by 309
Supramolecular Block Copolymers with Cucurbit[8]uril in Water
Rauwald, U., & Scherman, O. A. (2008) · Angewandte Chemie International Edition · doi:10.1002/anie.200705591 · Cited by 296
Xu, J., Wang, X., Zhang, X., Zhang, Y., Yang, Z., Li, S., Tao, L., Wang, Q., & Wang, T. (2023) · Chemical Engineering Journal · doi:10.1016/j.cej.2022.138673 · Cited by 284
Wei, M., Zhan, M., Yu, D., Xie, H., He, M., Yang, K., & Wang, Y. (2015) · ACS Applied Materials & Interfaces · doi:10.1021/am507575z · Cited by 153
Krieg, E., Weissman, H., Shimoni, E., Bar On (Ustinov), A., & Rybtchinski, B. (2014) · Journal of the American Chemical Society · doi:10.1021/ja503906p · Cited by 79
Chang, R., Huang, Y., Shan, G., Bao, Y., Yun, X., Dong, T., & Pan, P. (2015) · Polymer Chemistry · doi:10.1039/c5py00742a · Cited by 72
Watts, A., & Hillmyer, M. A. (2019) · Biomacromolecules · doi:10.1021/acs.biomac.9b00411 · Cited by 59
Metadata
- Authors
- Söntjens, S. H. M., Sijbesma, R. P., van Genderen, M. H. P., & Meijer, E. W.
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2000-07-20
- Volume
- 122
- Issue
- 31
- Pages
- 7487-7493
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W1988653878
- Cited by
- 542
- References
- 14
- FWCI
- 8.15
- Type
- journal article
- Language
- en
- Open access
- closed
About these checks
Registry, retraction, Cites and statistics results are computed, not judged, with one exception: a printed reference that no index lists is read once by a model before it counts as a citation error. Claims are extracted by a model and kept only when their quote appears verbatim in the text; each cited source is then checked, with a model’s help, for whether it says what the claim relies on. Those verdicts can be wrong — read the claim’s quote and the cited source before relying on one.
Statistics and arithmetic are recomputed, not judged.
Confidence bands are shown only for fields calibrated on our annotated test set. None is calibrated yet, so no band is shown.
What counts as a claim ›How we measure confidence ›How we check this ›
Are you an author, or do you see a problem with this page? Request a review
Data sources
Bibliographic data: Semantic Scholar, OpenAlex, Crossref.
Contains information from the Semantic Scholar Academic Graph Datasets, made available under the ODC Attribution License (ODC-BY 1.0).
Semantic Scholar’s data is described in: Kinney, R., et al. (2023). The Semantic Scholar Open Data Platform. arXiv:2301.10140.
