A colorimetric proton sponge

Journal of Organic Chemistry

Volumn 75, Issue 20, 2010, Pages 6977-6979

  Swor, Charles D ^a   Zakharov, Lev N ^a   Tyler, David R ^a  

^a UNIVERSITY OF OREGON   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COLOR CHANGES; POSITIVE SOLVATOCHROMISM; PROTON SPONGE; PROTONATED; ROOM TEMPERATURE;

COLORIMETRY; NAPHTHALENE; OPTICAL PROJECTORS; PROTONS;

COLOR;

1,8 BIS(DIMETHYLAMINO)NAPHTHALENE; 3 [4,5 BIS(DIMETHYLAMINO)NAPTHALEN 1 YL]FURAN 2,5 DIONE; ACETONITRILE; ACID ANHYDRIDE; MALEIC ACID DERIVATIVE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; COLOR; COLORIMETRY; PROTON TRANSPORT; ROOM TEMPERATURE; SOLVATOCHROMISM; SOLVENT EFFECT; ULTRAVIOLET SPECTROSCOPY; X RAY CRYSTALLOGRAPHY;

1-NAPHTHYLAMINE; COLORIMETRY; CRYSTALLOGRAPHY, X-RAY; MALEIC ANHYDRIDES; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PROTONS; STEREOISOMERISM;

EID: 77957910131     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo101381r     Document Type: Article

References (35)

1. Alder, R. W.; Bowman, P. S.; Steele, W. R. S.; Winterman, D. R. Chem. Commun. 1968, 723-724
2. Kaljurand, I.; Kutt, A.; Soovali, L.; Rodima, T.; Maemets, V.; Leito, I.; Koppel, I. A. J. Org. Chem. 2005, 70, 1019-1028
3. Terrier, F.; Halle, J. C.; Pouet, M. J.; Simonnin, M. P. J. Org. Chem. 1986, 51, 409-411
4. Kurasov, L. A.; Pozharskii, A. F.; Kuzmenko, V. V.; Klyuev, N. A.; Chernyshev, A. I.; Goryaev, S. S.; Chikina, N. L. Zh. Org. Khim. 1983, 19, 590-597
5. Ozeryanskii, V. A.; Pozharskii, A. F.; Fomchenkov, A. M. Russ. Chem. Bull. 1998, 47, 313-317
6. Vistorobskii, N. V.; Pozharskii, A. F. Zh. Org. Khim. 1991, 27, 1543-1552
7. Ryabtsova, O. V.; Pozharskii, A. F.; Ozeryanskii, V. A.; Vistorobskii, N. V. Russ. Chem. Bull. 2001, 50, 854-859
8. Maresca, L.; Natile, G.; Fanizzi, F. P. J. Chem. Soc., Dalton Trans. 1992, 1867-1868
9. Chambers, R. D.; Korn, S. R.; Sandford, G. Tetrahedron 1992, 48, 7939-7950
10. Chambers, R. D.; Korn, S. R.; Sandford, G. J. Chem. Soc., Chem. Commun. 1993, 856-857
11. Rozentsveig, I. B.; Levkovskaya, G. G.; Mirskova, A. N.; Kozyreva, O. B. Russ. J. Org. Chem. 1997, 33, 565-566
12. Lee, Y.; Kitagawa, T.; Komatsu, K. J. Org. Chem. 2004, 69, 263-269
13. Fenske, D.; Becher, H. J. Chem. Ber. 1974, 107, 117-122
14. Mao, F.; Tyler, D. R.; Keszler, D. J. Am. Chem. Soc. 1989, 111, 130-134
15. van Doorn, J.; A., J. H. G.; Meijboom, N. J. Chem. Soc., Perkin Trans. 2 1990, 479-485
16. Pozharskii, A. F.; Ozeryanskii, V. A. Proton Sponges. In The Chemistry of Anilines; John Wiley & Sons Ltd., 2007; Vol. 2, pp 931 - 1139.
17. Einspahr, H.; Robert, J. B.; Marsh, R. E.; Roberts, J. D. Acta Crystallogr. B Struct. Crystallogr. Cryst. Chem. 1973, 29, 1611-1617
18. Korzhenevskaya, N. G.; Schroeder, G.; Brzezinski, B.; Rybachenko, V. I. Russ. J. Org. Chem. 2001, 37, 1603-1610
19. Reichardt, C. Chem. Rev. 1994, 94, 2319-2358
20. Pozharskii, A. F.; Kuzmenko, V. V.; Aleksandrov, G. G.; Dmitrienko, D. V. Russ. J. Org. Chem. 1995, 31, 525
21. Szemik-Hojniak, A.; Deperasinska, I.; Buma, W.; Balkowski, G.; Pozharskii, A.; Vistorobskii, N.; Allonas, X. Chem. Phys. Lett. 2005, 401, 189-195
22. Pozharskii, A.; Vistorobskii, N.; Bardin, A.; Filatova, E. Russ. J. Org. Chem. 2006, 42, 131-135
23. Mekh, M. A.; Pozharskii, A. F.; Ozeryanskii, V. A. Pol. J. Chem. 2009, 83, 1609-1621
24. Abraham, M. H.; Grellier, P. L.; Prior, D. V.; Duce, P. P.; Morris, J. J.; Taylor, P. J. J. Chem. Soc., Perkin Trans. 2 1989, 699-711
25. Mulliken, R. S. J. Am. Chem. Soc. 1952, 74, 811-824
26. Rosokha, S. V.; Kochi, J. K. J. Org. Chem. 2002, 67, 1727-1737
27. McKusick, B. C.; Heckert, R. E.; Cairns, T. L.; Coffman, D. D.; Mower, H. F. J. Am. Chem. Soc. 1958, 80, 2806-2815
28. Martin, E. L.; Dickinson, C. L.; Roland, J. R. J. Org. Chem. 1961, 26, 2032-2037
29. Martin, E. L. Substituted Maleic Anhydrides and the Corresponding Lactones of 3-Formylacrylic Acid. U.S. Patent 3,113,939, Dec 10, 1963.
30. Kadlecek, D. E.; Hong, D.; Carroll, P. J.; Sneddon, L. G. Inorg. Chem. 2004, 43, 1933-1942
31. Tomoi, M.; Suzuki, T.; Kakiuchi, H. Makromol. Chem., Rapid Commun. 1987, 8, 291-296
32. Corma, A.; Iborra, S.; Rodríguez, I.; Sánchez, F. J. Catal. 2002, 211, 208-215
33. Bruker SMART and SAINT; Bruker AXS, Inc.: Madison, WI, 2000.
34. Sheldrick, G. M. SADABS; University of Göttingen: Germany, 1995.
35. Sheldrick, G. M. Acta Crystallogr. A 2008, 64, 112-122