Nitrogen-halogen intermolecular forces in solution [22]

Journal of the American Chemical Society

Volumn 121, Issue 34, 1999, Pages 7973-7974

  Wash, Paul L ^a   Ma, Shihong ^a   Obst, Ulrike ^a   Rebek Jr , Julius ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

BENZENE; HALOGEN; NITROGEN; PHENAZINE; XANTHENE;

CHEMICAL STRUCTURE; CONTROLLED STUDY; FORCE; HYDROGEN BOND; LETTER; MOLECULAR INTERACTION; MOLECULAR RECOGNITION;

EID: 0033198577     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991653m     Document Type: Letter

References (18)

1. Paliwal, S.; Geib, S.; Wilcox, C. S. J. Am. Chem. Soc. 1994, 116, 4497-4498.
2. Adams, H.; Carver, F. J.; Hunter, C. A.; Morales, J. C.; Seward, E. M. Angew. Chem., Int. Ed. Engl. 1996, 35, 1542-1544.
3. Kato, Y.; Conn, M. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1994, 116, 3279-3284.
4. Kato, Y.; Conn, M. M.; Rebek, J., Jr. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 1208-1212.
5. Bent, H. A. Chem. Rev. 1968, 68, 587-648.
6. Lommerse, J. P. M.; Stone, A. J.; Taylor, R.; Allen, F. H. J. Am. Chem. Soc. 1996, 118, 3108-3116.
7. Desiraju, G. R.; Harlow, R. L. J. Am. Chem. Soc. 1989, 111, 6757-6764.
8. Xu, K.; Ho, D. M.; Pascal, R. A., Jr. J. Am. Chem. Soc. 1994, 116, 105-110.
9. Amico, V.; Meille, S. V.; Corradi, E.; Messina, M. T.; Resnati, G. J. Am. Chem. Soc. 1998, 120, 8261-8262.
10. Reddy, D. S.; Panneerselvam, K.; Pilati, T.; Desiraju, G. R. J. Chem. Soc., Chem. Commun. 1993, 661-662.
11. Xu, K.; Ho, D. M.; Pascal, R. A. J. Org. Chem. 1995, 60, 7186-7191.
12. Blackstock, S. C.; Kochi, J. K.; Lorand, J. P. J. Org. Chem. 1987, 52, 1451-1460.
13. Initial studies involving symmetrically substituted cleft compounds (containing two convergent aromatic bromines in the C isomer) failed to show interaction with such guests as phenazine, DABCO, and 1,4-benzoquinone; all suitable guests with nucleophilic heteroatoms are presented in the required collinear arrangement. In these cases, C and S isomers of the dibromides were assigned by the X-ray structure determination of a suitable crystal grown of the S isomer. A standard crystallographer's report can be found in the Supporting Information.
14. Shimizu, K. D.; Dewey, T. M.; Rebek, J., Jr. J. Am. Chem. Soc. 1994, 116, 5145-5149. Similar solid-state evidence of pyramidalization at the imide nitrogen is present in the X-ray structure described in ref 13.
15. Huq, A. K. M. S.; Lodhi, S. A. K. J. Phys. Chem. 1966, 70, 1354-1358.
16. Langhals, H.; Ismael, R. Eur. J. Org. Chem. 1998, 1915, 5-1917. Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793-1796.
17. Langhals, H.; Ismael, R. Eur. J. Org. Chem. 1998, 1915, 5-1917. Nelson, J. C.; Saven, J. G.; Moore, J. S.; Wolynes, P. G. Science 1997, 277, 1793-1796.
18. Benisi, H. A.; Hildebrand, J. H. J. Am. Chem. Soc. 1949, 71, 2703-2707.