A novel indicator series for measuring pKa values in acetonitrile

Tetrahedron

Volumn 60, Issue 34, 2004, Pages 7287-7292

  Heemstra, Jennifer M ^a   Moore, Jeffrey S ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

Azobenzene; Indicator; Organic base

Indexed keywords

ACETONITRILE; AZOBENZENE; DYE;

ABSORPTION SPECTROSCOPY; CONFERENCE PAPER; LIGHT ABSORPTION; PRIORITY JOURNAL; PROTON TRANSPORT;

EID: 3343012153     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.05.019     Document Type: Conference Paper

References (21)

1. Paquette L.A. Encyclopedia of Reagents for Organic Synthesis. 1995;Wiley, Chichester
2. Reich H.J., Rigby J.H. Handbook of Reagents for Organic Synthesis: Acidic and Basic Reagents. 1999;Wiley, Chichester
3. Tang J., Dopke J., Verkade J.G. J. Am. Chem. Soc. 115:1993;5015-5020
4. Schwesinger R., Schlemper H., Hasenfratz C., Willaredt J., Dambacher T., Breuer T., Ottaway C., Fletschinger M., Boele J., Fritz H., Putzas D., Rotter H.W., Bordwell F.G., Satish A.V., Ji G.-Z., Peters E.-M., Peters K., von Schnering H.G., Walz L. Liebigs Ann. 1996;1055-1081
5. Sigma-Aldrich Chemfiles. Strong and Hindered Bases in Organic Synthesis. http://www.sigmaaldrich.com/aldrich/brochure/al_chemfile_v3_no1.pdf (accessed Dec 2003).
6. a values. http://www.courses.fas.harvard.edu/~chem206/Fall_2001/ lectures/18_Acid_Based_Properties_of_Organic_Molecules/pKa_compilation.pdf (accessed Sept 2003).
7. Heemstra J.M., Moore J.S. Org. Lett. 6:2004;659-662
8. Izutsu K. Acid-Base Dissociation Constants in Dipolar Aprotic Solvents. IUPAC Chemical Data Series No. 35. 1990;Blackwell Scientific, Oxford
9. Leito I., Kaljurand I., Koppel I.A., Yagupolskii L.M., Vlasov V.M. J. Org. Chem. 63:1998;7868-7874
10. Kaljurand I., Rodima T., Leito I., Koppel I.A., Schwesinger R. J. Org. Chem. 65:2000;6202-6208
11. Swain M., Woodward C.F., Brice B.A. J. Am. Chem. Soc. 71:1949;1341-1345
12. Augustin-Nowacka D., Makowski M., Chmurzynski L. Anal. Chim. Acta. 418:2000;233-240
13. Fortune W.B., Mellon M.G. J. Am. Chem. Soc. 60:1938;2607-2609
14. Kurtoglu M., Birbiçer N., Kimyonsen Ü., Serin S. Dyes Pigments. 41:1999;143-147
15. Giumanini A.G., Chiavari G., Musiani M.M., Rossi P. Synthesis. 1980;743-746
16. a values refer to the dissociation constant of the protonated azobenzene indicator
17. Carey F.A., Sundberg R.J. Advanced Organic Chemistra, Part A: Structure and Mechanisms. 4th ed.:2000;Kluwer Academic/Plenum, New York
18. Ege S.N. Organic Chemistry: Structure and Reactivity. 3rd ed.:1994;DC Heath and Company, Lexington, Massachusetts
19. Vaidyanathan S. Indian J. Chem. 11:1973;400
20. Nishimura N., Kosako S., Sueishi Y. Bull. Chem. Soc. Jpn. 57:1984;1617-1625
21. Skulski K. Bull. Acad. Pol. Sci. Ser. Sci. Chim. 21:1973;859-868