Amino acid alanine reactivity with the fingerprint reagent ninhydrin. A detailed ab initio computational study

Journal of Forensic Sciences

Volumn 51, Issue 6, 2006, Pages 1267-1275

  Petraco, Nicholas D K ^a,b   Proni, Gloria ^a   Jackiw, Jennifer J ^a   Sapse, Anne Marie ^a,b  

^a JOHN JAY COLLEGE OF CRIMINAL JUSTICE   (United States)

^b CITY UNIVERSITY OF NEW YORK   (United States)

Author keywords

Computational; Forensic chemistry; Forensic science; Hartree fock SCF calculations; Mechanism; Ninhydrin; Quantum chemistry; Ruhemann's Purple

Indexed keywords

ACETALDEHYDE; ALANINE; AMINO ACID; NINHYDRIN; REAGENT; RUHEMANN PURPLE;

AB INITIO CALCULATION; ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; COLOR; DENSITY FUNCTIONAL THEORY; ENERGY TRANSFER; FEASIBILITY STUDY; FINGER DERMATOGLYPHICS; FORENSIC SCIENCE; GEOMETRY; HARTREE FOCK SELF CONSISTENT FIELD CALCULATION; HIGH TEMPERATURE; HUMAN; ISOMER; POROSITY; PRIORITY JOURNAL; QUANTUM CHEMISTRY; QUANTUM MECHANICS; REACTION ANALYSIS; ROOM TEMPERATURE;

ALANINE; DERMATOGLYPHICS; HUMANS; INDICATORS AND REAGENTS; MODELS, CHEMICAL; MOLECULAR STRUCTURE; NINHYDRIN;

EID: 33845576369     PISSN: 00221198     EISSN: 15564029     Source Type: Journal    
DOI: 10.1111/j.1556-4029.2006.00271.x     Document Type: Article

References (36)

1. Gaensslen RE, Young KR. Fingerprints. In: James SH, Nordby JJ, editors. Forensic science. An introduction to scientific and investigative techniques. New York, NY: CRC Press, 2005. pp. 341-60.
2. Berry J, Stoney DA. History and development of fingerprinting. In: Lee HC, Gaensslen RE, editors. Advances in fingerprint technology. 2nd ed. New York, NY: CRC Press, 2001. pp. 1-41.
3. Margot P, Lennard C. Fingerprint detection techniques. Lausanne: Universite de Lausanne, 1994.
4. Joullie MM, Thompson TR, Nemeroff NH. Ninhydrin and ninhydrin analogs. Syntheses and applications. Tetrahedron 1991;47:8791.
5. Lennard CJ, Margot PA, Stoilovic M, Warrener RN. Synthesis and evaluation of ninhydrin analogues as reagents for the development of latent fingerprints on paper surfaces. J Forensic Sci Soc 1988;28:3-23.
6. Calvin M, Wood CL. Conjugation of carbonyl groups and the absorption spectrum of triketopentane. J Am Chem Soc 1940;62:3152-5.
7. Almog J. Fingerprint development by ninhydrin and its analogues. In: Lee HC, Gaensslen RE, editors. Advances in fingerprint technology. 2nd ed. New York, NY: CRC Press, 2001. pp. 177-210.
8. Pounds CA. Developments in fingerprint visualization. In: Maehly A, Williams RL, editors. Forensic science progress. Berlin: Springer, 1988. pp. 96-119.
9. Pounds CA, Grigg R, Mongkolaussavaratana T. The use of 1,8-diazafluoren-9-one (DFO) for fluorescent detection of latent fingerprints on paper. A preliminary evaluation. J Forensic Sci 1990;35:169.
10. Menzel ER. Fingerprint detection with lasers. 2nd ed. New York, NY: Marcel Dekker, 1999.
11. Johnson AW, McCaldin DJ. Formation of yellow condensation products from amino compounds and ninhydrin. J Chem Soc 1958;158:817.
12. McCaldin DJ. The chemistry of ninhydrin. Chem Rev 1960;60:39.
13. Lamothe PJ, McCormick PG. Influence of acidity on the reaction of ninhydrin with amino acids. Anal Chem 1972;44:821.
14. Lamothe PJ, McCormick PG. Role of hydrindantin in the determination of amino acids using ninhydrin. Anal Chem 1973;45:1906.
15. Friedman M, Williams LD. Stoichiometry of formation of Ruhemann's Purple in the ninhydrin reaction. Bioorg Chem 1974;3:267.
16. Friedman M. Applications of the ninhydrin reaction for analysis of amino acids, peptides, and proteins to agricultural and biomedical sciences. J Agric Food Chem 2004;52:385.
17. Hehre WJ, Kong J. Spartan '04 windows. Irvine, CA: Wavefunction Inc, 2004.
18. Hehre WJ, Ditchfield R, Pople JA. Self-consistent molecular orbital methods. Xii. Further extensions of gaussian - type basis sets for use in molecular orbital studies of organic molecules. J Chem Phys 1972;56:2257.
19. Hariharan PC, Pople JA. The influence of polarization functions on molecular orbital hydrogenation energies. Theor Chim Acta 1973;28:213.
20. MacFayden DA, Fowler NJ. On the mechanism of the reaction of ninhydrin with amino acids. II. A spectrophotometric study of hydrindantin reactions. J Bio Chem 1950;186:13.
21. Schonberg A, Moubasher R. The Strecker degradation of α-amino acids. Chem Rev 1952;50:261.
22. Wittmann H, Muller AK, Ziegler E. New reagents for the detection of amino acids by paper chromatography. V. Reaction of 1.2.3-trioxo-2.3- dihydrophenylene. Monatsh Chem 1969;100:497.
23. Schertz TD, Reiter RC, Stevenson CD. Zwitterion radicals and anion radicals from electron transfer and solvent condensation with the fingerprint developing agent ninhydrin. J Org Chem 2001;66:7596-603.
24. Dietz F, Rommel-Mohle K, Schleitzer A, Tyutyulkov N. On the chromophore of the ninhydrin-amino acid color reaction. Z fur Naturforschung 1993;48b:1133-7.
25. Wigfield DC, Buchanan GW, Croteau SM. On Ruhemann's purple. Can J Chem 1980;58:201-8.
26. Grigg R, Malone JF, Mongkolaussavaratana T, Thianpatanagul S. X = Y - Z compounds as potential 1,3-dipoles. Part 23: 1,2 mechanisms of the reactions of ninhydrin and phenalene trion with proportional to-amino acids. X-ray crystal structure of protonated Ruhemann's Purple, a stable azomethine ylide. Tetrahedron 1989;45:3849-62.
27. Grigg R, Malone JF, Mongkolaussavaratana T, Thianpatanagul S. Cycloaddition reactions relevant to the mechanism of the ninhydrin reaction. X-ray crystal structure if the protonated Ruhemann's Purple, a stable 1,3-dipole. J Chem Soc Chem Commun 1986:421-2.
28. Pine SH, Hendrickson JB, Cram DJ, Hammond GS. Organic chemistry. 4th ed. New York: McGraw-Hill, 1980.
29. Elber R, Frank A, Almog J. Chemical development of latent fingerprints: computational design of ninhydrin analogues. J Forensic Sci 2000;45:757-60.
30. Ruhemann S. Cyclic di- and tri-ketones. Trans Chem Soc 1910;97:1438.
31. Ruhemann S. Triketohydrindene hydrate. Trans Chem Soc 1910;97:2025.
32. Ruhemann S. Triketohydrindene hydrate. III. Its relation to alloxan. Trans Chem Soc 1911;99:792.
33. Ruhemann S. Triketohydrindene hydrate. IV. Hydrindantin and its analogs. Trans Chem Soc 1911;99:1306.
34. Ruhemann S. Triketohydrindene hydrate. V. The analogs of uramil and purpuric acid. Trans Chem Soc 1911;99:1486.
35. Ruhemann S. Triketomethylenedioxyhydrindene. Trans Chem Soc 1912;101:780.
36. Rubin M. Chemistry of vicinal polyketones. Chem Rev 1975;75:177.