Photoacoustic FTIR spectroscopy, a nondestructive method for sensitive analysis of solid-phase organic chemistry

Journal of Organic Chemistry

Volumn 61, Issue 23, 1996, Pages 7980-7981

  Gosselin, Francis ^a   Di Renzo, Mauro ^a   Ellls, Thomas H ^a   Lubell, William D ^a  

^a UNIVERSITÉ DE MONTRÉAL   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000683556     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961393g     Document Type: Article

References (35)

1. FTIR spectroscopy of KBr pellets is described in: (a) Crowley, J. I.; Rapoport, H. J. Org. Chem. 1980, 45, 3215. (b) Frechet, J. M.; Schuerch, C. J. J. Am. Chem. Soc. 1971, 95, 492. The use of FTIR spectroscopy of KBr pellets in combinatorial syntheses is described in: (c) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. (d) Kurth, M. J.; Allbergh Randall, L. A.; Chen, C.; Melander, C.; Miller, R. B.; McAlister, K.; Reitz, G.; Rang, R.; Nakatsu, T.; Green, C. J. Org. Chem. 1994, 59, 5862. (e) Chen, C.; Allbergh Randall, L. A.; Miller, R. B.; Jones, A. D.; Kurth, M. J. J. Am. Chem. Soc. 1994, 116, 2661.
2. FTIR spectroscopy of KBr pellets is described in: (a) Crowley, J. I.; Rapoport, H. J. Org. Chem. 1980, 45, 3215. (b) Frechet, J. M.; Schuerch, C. J. J. Am. Chem. Soc. 1971, 95, 492. The use of FTIR spectroscopy of KBr pellets in combinatorial syntheses is described in: (c) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. (d) Kurth, M. J.; Allbergh Randall, L. A.; Chen, C.; Melander, C.; Miller, R. B.; McAlister, K.; Reitz, G.; Rang, R.; Nakatsu, T.; Green, C. J. Org. Chem. 1994, 59, 5862. (e) Chen, C.; Allbergh Randall, L. A.; Miller, R. B.; Jones, A. D.; Kurth, M. J. J. Am. Chem. Soc. 1994, 116, 2661.
3. FTIR spectroscopy of KBr pellets is described in: (a) Crowley, J. I.; Rapoport, H. J. Org. Chem. 1980, 45, 3215. (b) Frechet, J. M.; Schuerch, C. J. J. Am. Chem. Soc. 1971, 95, 492. The use of FTIR spectroscopy of KBr pellets in combinatorial syntheses is described in: (c) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. (d) Kurth, M. J.; Allbergh Randall, L. A.; Chen, C.; Melander, C.; Miller, R. B.; McAlister, K.; Reitz, G.; Rang, R.; Nakatsu, T.; Green, C. J. Org. Chem. 1994, 59, 5862. (e) Chen, C.; Allbergh Randall, L. A.; Miller, R. B.; Jones, A. D.; Kurth, M. J. J. Am. Chem. Soc. 1994, 116, 2661.
4. FTIR spectroscopy of KBr pellets is described in: (a) Crowley, J. I.; Rapoport, H. J. Org. Chem. 1980, 45, 3215. (b) Frechet, J. M.; Schuerch, C. J. J. Am. Chem. Soc. 1971, 95, 492. The use of FTIR spectroscopy of KBr pellets in combinatorial syntheses is described in: (c) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. (d) Kurth, M. J.; Allbergh Randall, L. A.; Chen, C.; Melander, C.; Miller, R. B.; McAlister, K.; Reitz, G.; Rang, R.; Nakatsu, T.; Green, C. J. Org. Chem. 1994, 59, 5862. (e) Chen, C.; Allbergh Randall, L. A.; Miller, R. B.; Jones, A. D.; Kurth, M. J. J. Am. Chem. Soc. 1994, 116, 2661.
5. FTIR spectroscopy of KBr pellets is described in: (a) Crowley, J. I.; Rapoport, H. J. Org. Chem. 1980, 45, 3215. (b) Frechet, J. M.; Schuerch, C. J. J. Am. Chem. Soc. 1971, 95, 492. The use of FTIR spectroscopy of KBr pellets in combinatorial syntheses is described in: (c) Moon, H.-s.; Schore, N. E.; Kurth, M. J. J. Org. Chem. 1992, 57, 6088. (d) Kurth, M. J.; Allbergh Randall, L. A.; Chen, C.; Melander, C.; Miller, R. B.; McAlister, K.; Reitz, G.; Rang, R.; Nakatsu, T.; Green, C. J. Org. Chem. 1994, 59, 5862. (e) Chen, C.; Allbergh Randall, L. A.; Miller, R. B.; Jones, A. D.; Kurth, M. J. J. Am. Chem. Soc. 1994, 116, 2661.
6. Single-bead FTIR microspectroscopy is presented in: (a) Yan, B.; Kumaravel, G.; Anjaria, H.; Wu, A.; Petter, R.; Jewell, C. F.; Wareing, J. R. J. Org. Chem. 1995, 60, 5736. (b) Yan, B.; Kumaravel, G. Tetrahedron 1996, 52, 843.
7. Single-bead FTIR microspectroscopy is presented in: (a) Yan, B.; Kumaravel, G.; Anjaria, H.; Wu, A.; Petter, R.; Jewell, C. F.; Wareing, J. R. J. Org. Chem. 1995, 60, 5736. (b) Yan, B.; Kumaravel, G. Tetrahedron 1996, 52, 843.
8. Internal reflection FTIR spectroscopy of injection molded high density polystyrene ("Mega-Crowns") is described in: Gremlich, H.-U.; Berets, S. L. Appl. Spectrosc. 1996, 50, 532.
9. Recent NMR techniques for the analysis of solid-phase synthesis resins are presented in: (a) Keifer, P. A. J. Org. Chem. 1996, 61, 1558. (b) Sarkar, S. K.; Garigipati, R. S.; Adams, J. L.; Keifer, P. A. J. Am. Chem. Soc. 1996, 118, 2305. (c) Garigipati, R. S.; Adams, B.; Adams, J. L.; Sarkar, S. K. J. Org. Chem. 1996, 61, 2911. (d) Anderson, R. C.; Jarema, M. A.; Shapiro, M. J.; Stokes, J. P.; Zilox, M. J. Org. Chem. 1995, 60, 2650. (e) Fitch, W. L.; Detre, G.; Holmes, C. P.; Shoolery, J. N.; Keifer, P. A. J. Org. Chem. 1994, 59, 7995.
10. Recent NMR techniques for the analysis of solid-phase synthesis resins are presented in: (a) Keifer, P. A. J. Org. Chem. 1996, 61, 1558. (b) Sarkar, S. K.; Garigipati, R. S.; Adams, J. L.; Keifer, P. A. J. Am. Chem. Soc. 1996, 118, 2305. (c) Garigipati, R. S.; Adams, B.; Adams, J. L.; Sarkar, S. K. J. Org. Chem. 1996, 61, 2911. (d) Anderson, R. C.; Jarema, M. A.; Shapiro, M. J.; Stokes, J. P.; Zilox, M. J. Org. Chem. 1995, 60, 2650. (e) Fitch, W. L.; Detre, G.; Holmes, C. P.; Shoolery, J. N.; Keifer, P. A. J. Org. Chem. 1994, 59, 7995.
11. Recent NMR techniques for the analysis of solid-phase synthesis resins are presented in: (a) Keifer, P. A. J. Org. Chem. 1996, 61, 1558. (b) Sarkar, S. K.; Garigipati, R. S.; Adams, J. L.; Keifer, P. A. J. Am. Chem. Soc. 1996, 118, 2305. (c) Garigipati, R. S.; Adams, B.; Adams, J. L.; Sarkar, S. K. J. Org. Chem. 1996, 61, 2911. (d) Anderson, R. C.; Jarema, M. A.; Shapiro, M. J.; Stokes, J. P.; Zilox, M. J. Org. Chem. 1995, 60, 2650. (e) Fitch, W. L.; Detre, G.; Holmes, C. P.; Shoolery, J. N.; Keifer, P. A. J. Org. Chem. 1994, 59, 7995.
12. Recent NMR techniques for the analysis of solid-phase synthesis resins are presented in: (a) Keifer, P. A. J. Org. Chem. 1996, 61, 1558. (b) Sarkar, S. K.; Garigipati, R. S.; Adams, J. L.; Keifer, P. A. J. Am. Chem. Soc. 1996, 118, 2305. (c) Garigipati, R. S.; Adams, B.; Adams, J. L.; Sarkar, S. K. J. Org. Chem. 1996, 61, 2911. (d) Anderson, R. C.; Jarema, M. A.; Shapiro, M. J.; Stokes, J. P.; Zilox, M. J. Org. Chem. 1995, 60, 2650. (e) Fitch, W. L.; Detre, G.; Holmes, C. P.; Shoolery, J. N.; Keifer, P. A. J. Org. Chem. 1994, 59, 7995.
13. Recent NMR techniques for the analysis of solid-phase synthesis resins are presented in: (a) Keifer, P. A. J. Org. Chem. 1996, 61, 1558. (b) Sarkar, S. K.; Garigipati, R. S.; Adams, J. L.; Keifer, P. A. J. Am. Chem. Soc. 1996, 118, 2305. (c) Garigipati, R. S.; Adams, B.; Adams, J. L.; Sarkar, S. K. J. Org. Chem. 1996, 61, 2911. (d) Anderson, R. C.; Jarema, M. A.; Shapiro, M. J.; Stokes, J. P.; Zilox, M. J. Org. Chem. 1995, 60, 2650. (e) Fitch, W. L.; Detre, G.; Holmes, C. P.; Shoolery, J. N.; Keifer, P. A. J. Org. Chem. 1994, 59, 7995.
14. In situ mass spectrometry of solid-phase resins is presented in: (a) Egner, B. J.; Cardno, M.; Bradley, M. J. Chem. Soc., Chem. Commun. 1995, 2163. (b) Egner, B. J.; Langley, G. J.; Bradley, M. J. Org. Chem. 1995, 60, 2652.
15. In situ mass spectrometry of solid-phase resins is presented in: (a) Egner, B. J.; Cardno, M.; Bradley, M. J. Chem. Soc., Chem. Commun. 1995, 2163. (b) Egner, B. J.; Langley, G. J.; Bradley, M. J. Org. Chem. 1995, 60, 2652.
16. Chemical techniques are discussed in: Chu, S. S,; Reich, S. H. Bioorg. Med. Chem. Lett. 1995, 5, 1053 and ref 4 therein.
17. Skoog, D. A.; Leary, J. J. Principles of Instrumental Analysis, 4th ed.; Saunders College: Orlando, FL, 1992; Chapter 8, pp 168-170; Chapter 12, pp 285.
18. Reviewed in: Rosencwaig, A. Photoacoustics and Photoacoustic Spectroscopy; Wiley: New York, 1980.
19. Bertrand, L.; Monchalin, J.-P.; Lepoutre, F. Appl. Optics 1982, 21, 248.
20. Rapp, W. Macrobeads as Microreactors: New Solid Phase Synthesis Methodology. In Combinatorial Chemistry: Synthesis and Application; Wilson, S., Czarnik, A. W., Eds.; Wiley: New York, 1996; Chapter 4, p 75.
21. Di Renzo, M.; Ellis, T. H.; Domingue, A.; Bertrand, L.; Sacher E.; Stangel, I. J. Adhesion 1994, 47, 115.
22. Gillis-D'Hamere, I.; Vrancken, K. C.; Vansant, E. F.; De Roy, G. J. Chem. Soc., Faraday Trans. 1992, 88, 2047.
23. Jurdana L. E.; Ghiggino K. P.; Leaver I. H.; Barraclough C. G.; Cole-Clarke, P. Appl. Spectrosc. 1994, 48, 44.
24. Sowa, M. G.; Mantsch, H. H. Appl. Spectrosc. 1994, 48, 316.
25. Urban, M. W.; Salazar-Rojas, E. M. J. Polymer Chem. 1990, 28, 1593.
26. Vidrine, W. D. Appl. Spectrosc. 1980, 34, 314.
27. Merrifield, R. B. J. Am. Chem. Soc. 1963, 85, 2149. The resin was 1% cross-linked with divinylbenzene, 1 mequiv of Cl/g.
28. -1. Helium was used as the carrier gas. PA spectra were ratioed against carbon black spectra obtained from the reference from MTEC photoacoustics.
29. Absorption spectra were taken on the spectrometer described in ref 18 using a DTGS detector with the samples pressed in KBr pellets. One hundred spectra were co-added at a mirror speed of 0.6 cm/s (10 kHz) and ratioed against the source emission spectrum. Beyond ratioing and in one case spectral subtraction, the spectra were subjected to no other mathematical treatment such as smoothing or base-line correction.
30. KBr pellets were prepared according to the procedure described in ref 1a.
31. Resino amino esters were prepared according to: Gisin; B. F. Helv. Chim. Acta 1973, 56, 1476. Characteristic bands and PA-FTIR spectra are reported in the supporting information.
32. Assignments of spectral bands for different functional groups were made according to: Colthup, N. B.; Daly, N. H.; Wiberley, S. E. Introduction to Infrared and Roman Spectroscopy, 3rd ed.; Academic Press: San Diego, 1990.
33. For a related synthesis of resino dehydropeptide see: Ojima, I.; Tsai, C.-Y.; Zhang, Z. Tetrahedron Lett. 1994, 35, 5785. For comparison, we prepared methyl N-(p-cyanobenzoyl)dehydroalanine from methyl S-benzylcysteinate hydrochloride; experimental details and spectral data for all intermediates are presented in the supporting information.
34. The oxidation conditions were modified from: Kondo, K.; Nagishi, A.; Fukuyama, M. Tetrahedron Lett. 1969, 2461.
35. Kelly-Basetti, B. M.; Mackay, M. F.; Pereira, S. M.; Savage, G. P.; Simpson, G. W. Heterocycles 1994, 37, 529.