Erratum: Detection of Explosives via Photolytic Cleavage of Nitroesters and Nitramines (J. Org. Chem. (2011) 76:9 (2976−2993) DOI: 10.1021/jo200280c);Detection of explosives via photolytic cleavage of nitroesters and nitramines

Journal of Organic Chemistry

Volumn 76, Issue 9, 2011, Pages 2976-2993

  Andrew, Trisha L ^a   Swager, Timothy M ^a  

^a MASSACHUSETTS INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINES; CHROMOPHORES; EXPLOSIVES DETECTION; FLUORESCENCE; FLUORESCENCE SPECTROSCOPY; IRRADIATION; NITRATION; NITRIC OXIDE; NITROGEN OXIDES;

DETECTION OF EXPLOSIVES; DIMETHYLANILINES; METHYL ESTERS; MODEL COMPOUND; NITRAMINES; NITROESTERS; NO X; PHOTOFRAGMENTATION; SYNTHESISED; UV IRRADIATION;

EXPLOSIVES;

AMINE; CYCLONITE; ESTER DERIVATIVE; EXPLOSIVE; ORGANONITROGEN DERIVATIVE; PENTAERYTHRITYL TETRANITRATE; TRINITROTOLUENE;

ARTICLE; CHEMICAL STRUCTURE; ELECTROCHEMISTRY; MASS FRAGMENTOGRAPHY; PHOTOCATALYSIS; SYNTHESIS; THIN LAYER CHROMATOGRAPHY;

EID: 79955568491     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/acs.joc.2c03003     Document Type: Erratum

References (43)

1. Jungreis, E. Spot Test Analysis: Clinical, Environmental, Forensic, and Geochemical Applications, 2 nd ed.; John Wiley: New York, 1997.
2. For representative examples see: Che, Y.; Yang, X.; Liu, G.; Yu, C.; Ji, H.; Zuo, J.; Zhao, J.; Zang, L. J. Am. Chem. Soc. 2010, 132, 5743-5750
3. Lan, A.; Li, K.; Wu, H.; Olson, D. H.; Emge, T. J.; Ki, W.; Hong, M.; Li, J. Angew. Chem., Int. Ed. 2009, 48, 2334-2338
4. Tao, S.; Yin, J.; Li, G. J. Mater. Chem. 2008, 18, 4872-4878
5. Toal, S. J.; Trogler, W. C. J. Mater. Chem. 2006, 16, 2871-2883
6. Yang, J.-S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 5321-5322
7. Engel, Y.; Elnathan, R.; Pevzner, A.; Davidi, G.; Flaxer, E.; Patolsky, F. Angew. Chem., Int. Ed. 2010, 49, 6830-6835
8. Bruschini, C. Subsurf. Sens. Technol. Appl. 2001, 2, 299-336
9. Takats, Z.; Cotte-Rodriguez, I.; Talaty, N.; Chen, H.; Cooks, R. G. Chem. Commun. 2005, 1950-1952
10. Eilbert, R. F. In Aspects of Explosives Detection; Marshall, M.; Oxley, J. C., Eds.; Elsevier: London, 2009; pp 89-130.
11. Andrew, T. L.; Swager, T. M. J. Am. Chem. Soc. 2007, 129, 7254-7255
12. Cope, W. C.; Barab, J. J. Am. Chem. Soc. 1917, 39, 504-514
13. Balakrishnan, V. K.; Halasz, A.; Hawari, J. Environ. Sci. Technol. 2003, 37, 1838-1843
14. Greiss, P. Ber. Dtsch. Chem. Ges. 1879, 12, 427-434
15. The original reagent reported by Greiss was composed of sulfanilic acid and α-naphthylamine; however, a more stable version of this formulation (the Zeller-Greiss reagent) containing sulfanilamide and N -(α-naphthyl) ethylenediamine hydrochloride has since been adopted: Zeller, H. D. Analyst 1955, 80, 632-640
16. Hawari, J.; Halasz, A.; Groom, C.; Deschamps, S.; Paquet, L.; Beaulieu, C.; Corriveau, A. Environ. Sci. Technol. 2002, 36, 5117-5123
17. Just, C. L.; Schnoor, J. L. Environ. Sci. Technol. 2004, 38, 290-295
18. Burton, D. T.; Turley, S. D. Bull. Environ. Contam. Toxicol. 1995, 55, 89-95
19. Glover, D. J.; Hoffsommer, J. C. Technical Report for Naval Surface Weapons Center, Silver Spring, MD, February 1979.
20. Sanchez, J. C.; Trogler, W. C. J. Mater. Chem. 2008, 18, 3143-3156
21. Roos, B. D.; Brill, T. B. Combust. Flame 2002, 128, 181-190
22. Peyton, G. R.; LaFaivre, M. H.; Maloney, S. W. CERL Technical Report for US Army Corps of Engineers, Champaign, IL, November 1999.
23. Gowenlock, B. G.; Pfab, J.; Young, V. M. J. Chem. Soc., Perkin Trans. 2 1997, 915-919
24. Pace, M. D. J. Phys. Chem. 1994, 98, 6251-6257
25. Bark, L. S.; Catterall, R. Mikrochim. Acta 1960, 4, 553-558
26. Demethylation of DMA has been observed in other cases: Macdonald, T. L.; Gutheim, W. G.; Martin, R. B.; Guengerich, F. P. Biochemistry 1989, 28, 2071-2077
27. Doyle, M. P.; Can Lente, M. A.; Mowat, R.; Fobare, W. F. J. Org. Chem. 1980, 45, 2570-2575
28. DMNA generally displays a low fluorescence quantum yield (<5%) and is susceptible to photolytic cleavage upon excitation: Costela, A.; Garcia-Moreno, I.; Garcia, O.; Sastre, R. Chem. Phys. Lett. 2001, 347, 115-120 (laser irradiation at 337 nm)
29. Görner, H.; Döpp, D. Photochem. Photobiol. Sci. 2002, 1, 270-277
30. Donor-acceptor anilines containing a nitro group as the "acceptor" component have been previously shown to possess large molar extinction coefficients and moderate fluorescence quantum yields. For example, see: Gruen, H.; Görner, H. J. Phys. Chem. 1989, 93, 7144-7152
31. Compound 17 was synthesized following a previously published procedure (Campeau, L.-C.; Parisien, M.; Jean, A.; Fagnou, K. J. Am. Chem. Soc. 2006, 128, 581-590)but is also commercially available
32. Oka, H.; Kouno, H.; Tanaka, H. J. Mater. Chem. 2007, 17, 1209-1215
33. The poor reactivity of the hexafluoro-2-propanol group toward Friedel-Crafts reactions has been observed previously; see: Amara, J. P.; Swager, T. M. Macromolecules 2006, 39, 5753-5759 and references cited therein
34. Seo, E. T.; Nelson, R. F.; Fritsch, J. M.; Marcoux, L. S.; Leedy, D. W.; Adams, R. N. J. Am. Chem. Soc. 1966, 88, 3498-3503
35. Rathore, R.; Kumar, A. S.; Lindeman, S. V.; Kochi, J. K. J. Org. Chem. 1998, 63, 5847-5856
36. 3) was previously used to control mono-nitrate electron-rich calixarenes: Xu, B.; Swager, T. M. J. Am. Chem. Soc. 1993, 115, 1160-1162
37. Strongly solvent-dependent fluorescence quantum yields have been previously observed for donor-acceptor chromophores. For example, see ref 18.
38. Sheldrick, G. M. Acta Crystallogr. A 1990, 46, 467
39. Sheldrick, G. M. SHELXL 91, Universtität Göttingen, Göttingen, 1997.
40. Demas, J. N.; Crosby, G. A. J. Phys. Chem. 1971, 75, 991
41. For a representative reference on the procedure followed, see: Hill, R. D.; Puddephatt, R. J. J. Am. Chem. Soc. 1985, 107, 1218
42. Hatchard, C. G.; Parker, C. A. Proc. R. Soc. London A 1956, 235, 518
43. Craig, D. J. Am. Chem. Soc. 1935, 57, 195