pKa values and geometries of secondary and tertiary amines complexed to boronic acids - Implications for sensor design

Organic Letters

Volumn 3, Issue 9, 2001, Pages 1311-1314

  Wiskur, Sheryl L ^a   Lavigne, John J ^a   Ait Haddou, Hassan ^a   Lynch, Vincent ^a   Chiu, Yu Hung ^b   Canary, James W ^b   Anslyn, Eric V ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

^b NEW YORK UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BORONIC ACID DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PH; STRUCTURE ACTIVITY RELATION; X RAY CRYSTALLOGRAPHY;

AMINES; BORONIC ACIDS; CRYSTALLOGRAPHY, X-RAY; HYDROGEN-ION CONCENTRATION; MAGNETIC RESONANCE SPECTROSCOPY; MODELS, MOLECULAR; MOLECULAR STRUCTURE; QUATERNARY AMMONIUM COMPOUNDS; STRUCTURE-ACTIVITY RELATIONSHIP;

EID: 0035799849     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0156805     Document Type: Article

References (22)

1. Yoon, J.; Czarnik, A. W. J. Am. Chem. Soc. 1992, 114, 5874-5875.
2. James, T. D.; Sandanayake, K. R. A. S.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1994, 477-478.
3. Lavigne, J. J.; Anslyn, E. V. Angew. Chem., Int. Ed. 1999, 38, 3666-3669.
4. Ward, C. J.; Patel, P.; Ashton, P. R.; James, T. D. Chem. Commun. 2000, 229-230.
5. Wulff, G. Pure Appl. Chem. 1982, 54, 2093-2102.
6. Julliard, J.; Geugue, N. C. R. Acad. Paris C 1967, 264, 259-261.
7. Nöth, H.; Wrackmeyer, B. Nuclear Magnetic Properties of Boron. In Nuclear Magnetic Resonance Spectroscopy of Boron Compounds; Diehl, P., Fluck, E., Kosfeld, R., Eds.; NMR Basic Principles and Progress Series 14; Springer-Verlag: Berlin, 1978; pp 5-14, 287.
8. Lorand, J. P.; Edwards, J. O. J. Org. Chem. 1959, 24, 769-774.
9. Ait Haddou, H.; Anslyn, E. V. University of Texas at Austin, Austin, TX. Unpublished work, 2001.
10. (a) Metzger, A.; Anslyn, E. V. Angew. Chem., Int. Ed. 1998, 37, 649-652.
11. (b) Niikura, K.; Metzger, A.; Anslyn, E. V. J. Am. Chem. Soc. 1998, 120, 8533-8534.
12. (c) Niikura, K.; Bisson, A. P.; Anslyn, E. V. J. Chem. Soc., Perkin Trans. 2 1999, 1111-1114.
13. (d) Cabell, L. A.; Monahan, M.-K.; Anslyn, E. V. Tetrahedron Lett. 1999, 40, 7753-7756.
14. (a) Hawkins, R. T.; Snyder, H. R. J. Am. Chem. Soc. 1960, 82, 3863-3866.
15. (b) Hawkins, R. T.; Blackham, A. U. J. Org. Chem. 1967, 32, 597-600.
16. (c) Lavigne, J. J.; Anslyn, E. V. University of Texas at Austin, Austin, TX. Unpublished work, 2001.
17. Lavigne, J. J. Ph.D. Dissertation, University of Texas at Austin, 2000.
18. Potentiometric studies were conducted with a Brinkmann Titrino 702 autotitrator. A Metrohm combined pH glass electrode (Ag/AgCl) with 3 M NaCl internal filling solution was used. Measurements were taken at 25°C under nitrogen. About 100 data points were collected for each titration, and the analysis was carried out as described by Martell (see below). Equilibrium constants were calculated using the program BEST. All constants were determined using at least two independent titrations. Martell, A. E.; Motekaitis, R. J. Determination and Use of Stability Constants; VCH Publishers: New York, 1992.
19. 11B NMR spectra were obtained with a Bruker AMX-500 spectrometer. Quartz NMR tubes were used to limit background noise. The pH values of the solutions were adjusted between 1.6 and 11 and measured with an Orion 720A pH meter.
20. Toyota, S.; Futawaka, T.; Asakura, M.; Ikeda, H.; Oki, M. Organometallics 1998, 17, 4155-4163.
21. o))] = 0.0549 and a goodness of fit = 1.05. The molecule lies on a crystallographic 2-fold rotation axis passing through the central pyridine ring.
22. Bissel, R. A.; de Silva, A. P.; Gunaratne, H. Q. N.; Lynch, P. L. M.; Maguire, G. E. M.; McCoy, C. P.; Sandanayake, K. R. A. S. Top. Curr. Chem. 1993, 168, 223-264.