1,3-Bis(m-nitrophenyl)urea: An exceptionally good complexing agent for proton acceptors

Journal of the American Chemical Society

Volumn 110, Issue 17, 1988, Pages 5896-5897

  Etter, Margaret C ^a   Panunto, Thomas W ^a  

^a UNIVERSITY OF MINNESOTA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33845278631     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00225a049     Document Type: Article

References (8)

1. Etter, M. C. Isr. J. Chem. 1985, 25, 312–319. (b) Etter, M. C.; Urbanczyk-Lipkowska, Z.; Jahn, D. A.; Frye, J. S. J. Am. Chem. Soc. 1986, 108, 5871–5876. (c) Panunto, T. W.; Urbanczyk-Lipkowska, Z.; Johnson, R. B.; Etter, M. C. J. Am. Chem. Soc. 1987, 109, 7786–7797.
2. Etter, M. C. J. Am. Chem. Soc. 1982, 104, 1095–1096.
3. Etter, M. C.; Rasmussen, J. K.; Gleason, W. B.; Kress, R. B.; Duerst, R. W.; Gillard, R. D. J. Org. Chem. 1986, 51, 5405–5408. (b) Etter, M. C.; Baures, P. W. J. Am. Chem. Soc. 1988, 110, 639–640. (c) Mori, K.; Stein, Z.; Goldberg, I. J. Org. Chem. 1988, 53, 308–312.
4. Dannecker, W.; Kopf, J.; Rust, H. Cryst. Struct. Commun. 1979, 8, 429–432.
5. Taft reports a value of 0.71 for β(the solvatochromic parameter for proton-accepting strength) compared to 0.55 for THF and 0.94 for triphenylphosphine oxide (Kamlet, M. J.; Abboud, J.-L.M.; Abraham, M. H.; Taft, R. W. J. Org. Chem. 1983, 48, 2877–2887).
6. 2 analogues of 1, 1,8-biphenylenediol (Hine, J.; Hahn, S.; Miles, D. E. J. Org. Chem. 1986, 51, 577–584), and fluorinated alcohols (ref 5).
7. Groth, P. An Introduction to Chemical Crystallography; Wiley: New York, 1906; pp 29–30.
8. Taylor, R.; Kennard, O. J. Am. Chem. Soc. 1982, 104, 5063–5070.