Ethylenediamine at air/liquid and air/silica interfaces: Protonation versus hydrogen bonding investigated by sum frequency generation spectroscopy

Environmental Science and Technology

Volumn 40, Issue 5, 2006, Pages 1566-1572

  Xu, Man ^a   Liu, Dingfang ^a   Allen, Heather C ^a  

^a OHIO STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ADSORPTION; CHEMISORPTION; IMPURITIES; REACTION KINETICS; SILICA; SPECTROSCOPY;

MOLECULAR-SCALE INTERFACIAL INFORMATION; SILANOL; SUM FREQUENCY GENERATION SPECTROSCOPY; SURFACE SPECIFIC VIBRATIONAL SPECTROSCOPY;

HYDROGEN BONDS;

DIAMINE; ETHYLENEDIAMINE; HYDROGEN; MINERAL; OXIDE; PROTON; SILICON DIOXIDE;

ADSORPTION; CHEMISORPTION; HYDROGEN BONDS; IMPURITIES; REACTION KINETICS; SILICA; SPECTROSCOPY;

SPECTROSCOPY;

ADSORPTION; AIR; ARTICLE; COMPARATIVE STUDY; COMPLEX FORMATION; EXPERIMENTAL MODEL; HYDROGEN BOND; LIQUID; MOLECULAR INTERACTION; PKA; POLLUTANT; PROTON TRANSPORT; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; SPECTROSCOPY; SUM FREQUENCY GENERATION SPECTROSCOPY; TECHNIQUE;

AIR; ETHYLENEDIAMINES; HYDROGEN BONDING; PROTONS; SILICON DIOXIDE; SPECTRUM ANALYSIS; SURFACE TENSION;

EID: 33644863821     PISSN: 0013936X     EISSN: None     Source Type: Journal    
DOI: 10.1021/es051537l     Document Type: Article

References (53)

1. Al-Abadleh, H. A.; Grassian, V. H. Oxide surfaces as environmental interfaces. Surf. Sci. Rep. 2003, 52 (3-4), 63.
2. Usher, C. R.; Michel, A. E.; Grassian, V. H. Reactions on mineral dust. Chem. Rev. 2003, 103 (12), 4883.
3. Batista de Carvalho, L. A. E.; Lourenco, L. E.; Marques, M. P. M. Confirmational study of 1,2-diaminoethane by combined ab initio MO calculations and Raman spectroscopy. J. Mol. Struct. 1999, 482-483, 639.
4. C. I. C. A. Concise International Chemical Assessment Document 15: 1,2-Diaminoethane (Ethylenediamine); World Health Organization: Geneva, 1999.
5. Yang, R. S. H.; German, R. H.; Maronpot, R. R.; Mckelvey, J. A.; Weil, C. S.; Woodside, M. D. Acute and subchronic toxicity of ethylenediamine in laboratory animals. Fundam. and Appl. Toxicol. 1983, 3, 512.
6. Leung, H. W. Evaluation of the genotoxic potential of alkyleneamines. Mutat. Res. 1994, 320, 31.
7. Bultinck, P.; Goeminne, A.; Van de Vondel, D. Ab initio conformational analysis of the chelating bidentate ligands ethylenediamine and 1,3-propanediamine. J. Mol. Struct. (THEOCHEM) 1995, 339, 1.
8. Kazerouni, M. R.; Hedberg, L.; Hedberg, K. Conformational analysis. 16. Ethylenediamine. An electron-diffraction and ab initio investigation of molecular strcture, conformational composition, anti-gauche energy and entropy differences, and implications for internal hydrogen bonding. J. Am. Chem. Soc. 1994, 116, 5279.
9. Cetina, R.; Rubio, M.; Mora, M. A. Ethylenediamine. II. Dimers, geometry and energy of the intermolecylar hydrogen bond. Revista Latinoam. Quim. 1979, 10 (2), 50.
10. Adsorption on Silica Surface. In Surfactant Science Series; Papirer, E., Ed.; Marcel Dekker: New York, 2000; Vol. 90.
11. Vidyadhar, A.; Rao, K. H.; Chernyshova, I. V.; Pradip; Forssberg, K. S. E. Mechanisms of amine-quartz interaction in the absence and presence of alcohols studied by spectroscopic methods. J. Colloid Interface Sci. 2002, 256, 59.
12. Hirva, P.; Pakkanen, T. A. Modeling the interaction of amine bases on isolated and geminal hydroxyl groups on silica. Surf. Sci. 1992, 271, 530.
13. 13C NMR: Adsorption of amines on silica, alumina, and mixed silica-alumina. J. Catal. 1976, 44, 306.
14. McCain, K. S.; Schluesche, P.; Harris, J. M. Modifying the adsorption behavior of polyamidoamine dendrimers at silica surfaces investigated by total internal reflection fluorescence correlation spectroscopy. Anal. Chem. 2004, 76, 930.
15. 3, MgO and CaO: I. diethylamine and triethylamine. J. Catal. 1990, 121, 153.
16. Chabal, Y. J.; Hines, M. A.; Feijoo, D. Characterization of silicon surfaces and interfaces by optical vibrational spectroscopy. J. Vac. Sci. Technol., A 1995, 13 (3), 1719.
17. Shen, Y. R. A few selected applications of surface nonlinear optical spectroscopy. Appl. Phys. Sci. 1996, 93, 12104.
18. Richmond, G. L. Molecular bonding and interactions at aqueous surfaces as probed by vibrational sum frequency spectroscopy. Chem. Rev. 2002, 102 (8), 2693.
19. Eisenthal, K. B. Liquid interfaces probed by second-harmonic and sum-frequency spectroscopy. Chem. Rev. 1996,96 (4), 1343.
20. Shultz, M. J.; Baldelli, S.; Schnitzer, C.; Simonelli, D. Aqueous solution/air interfaces probed with sum fequency generation spectroscopy. J. Phys. Chem. B 2002, 106 (21), 5313.
21. Hommel, E. L.; Allen, H. C. 1-Methyl naphthalene reorientation at the air-liquid interface upon water saturation studied by vibrational broad bandwidth sum frequency generation spectroscopy. J. Phys. Chem. B 2003, 107, 10823.
22. Ma, G.; Allen, H. C. Diffuse reflection broad bandwidth sum frequency generation from particle surfaces. J. Am. Chem. Soc. 2002, 124 (32), 9374.
23. Shen, Y. R. Surface contribution versus bulk contribution in surface nonlinear optical spectroscopy. Appl. Phys. B 1999, 68, 295.
24. Miranda, P. B.; Shen, Y. R. Liquid interfaces: A study by sum-frequency vibrational spectroscopy. J. Phys. Chem. B 1999, 103, 3292.
25. Tadjeddine, A. Spectroscopic investigation of surfaces and interfaces by using infrared-visible sum and difference frequency generation. Surf. Rev. Lett. 2000, 7 (4), 423.
26. Shen, Y. R. Surface properties probed by second-harmonic and sum-frequency generation. Nature 1989, 337, 519.
27. Buck, M.; Himmelhaus, M. Vibrational spectroscopy of interfaces by infrared-visible sum frequency generation. J. Vac. Sci. Technol. A 2001, 19, 2717.
28. 2 film by sum frequency generation using methanol as a molecular probe. J. Phys. Chem. B 2004, 108, 265.
29. Shen, Y. R. The Principles of Nonlinear Optics, 1st ed.; John Wiley & Sons: New York, 1984.
30. Boyd, R. W. Nonlinear Optics, 1st ed.; Academic Press: Harcourt Brace Jovanovich, San Diego, 1992.
31. Hirose, C.; Akamatsu, N.; Domen, K. Formulas for the analysis of the surface SFG spectrum and transformation coefficients of cartesian SFG tensor components. Appl. Spectrosc. 1992, 46 (6), 1051.
32. Brown, M. G.; Raymond, E. A.; Allen, H. C.; Scatena, L. F.; Richmond, G. L. The analysis of interference effects in the sum frequency spectra of water interfaces. J. Phys. Chem. A 2000, 104, 10220.
33. 2 surfaces: Observation of molecular orientation and surface hydroxyl groups as sorption sites. Environ. Sci. Technol. 2005, 39, 206.
34. Yaws, C. L. Handbook of Vapor Pressure; Gulf Publishing Company: Houston, TX, 1994.
35. Jonsson, B.; B., L.; Holmberg, K.; Kronberg, B. Surfactants and Polymers in Aqueous Solution; John Wiley and Sons: New York, 1998.
36. Tyrode, E.; Johnson, C. M.; Baldelli, S.; Leygraf, C.; Rutland, M. W. A vibrational sum frequency spectroscopy study of the liquid-gas interface of acetic acid-water mixtures: 2. Orientation analysis. J. Phy. Chem. B 2005, 109, 329.
37. Defay, R.; Prigogine, I.; Bellemans, A. Surface Tension and Adsorption; John Wiley and Sons: New York, 1966.
38. Gopalakrishnan, S.; Jungwirth, P.; Tobias, D. J.; Allen, H. C. Air-liquid interfaces of aqueous solutions containing ammonium and sulfate: Spectroscopic and molecular dynamics studies. J. Phys. Chem. B 2005, 109 (18), 8861.
39. Allen, H. C.; Raymond, E. A.; Richmond, G. L. Nonlinear vibrational sum frequency generation spectroscopy of atmospherically relevant molecules at aqueous solution surfaces. Curr. Opin. Colloid Interface Sci. 2000, 5, 74.
40. Righini, R.; Califano, S. The vibrational optical spectrum of ethylenediamine crystal: Calculation of the one-phonon spectrum of the high-temperature crystal form. Chem. Phys. 1976, 17, 45.
41. Giorgini, M. G.; Pelletti, M. R.; Paliani, G.; Cataliotti, R. S. Vibrational spectra and assignments of ethylene-diamine and its deuterated derivatives. J. Raman Spectrosc. 1983, 14 (1), 16.
42. Hirose, C.; Akamatsu, N.; Domen, K. Formulas for the analysis of surface sum-frequency generation spectrum by CH stretching modes of methyl and methylene groups. J. Chem. Phys. 1992, 96 (2), 997.
43. Lu, R.; Can, W.; Wu, B.-H.; Chen, H.; Wang, H.-F. Vibrational polarization spectroscopy of CH stretching modes of the methylene group at the vapor/liquid interfaces with sum frequency generation. J. Phy. Chem. B 2004, 108, 7297.
44. Wei, X.; Hong, S.; Zhuang, X.; Goto, T.; Shen, Y. R. Nonlinear optical studies of liquid crystal alignment on a rubbed poly(vinyl alcohol) surface. Phys. Rev. E 2000, 62 (4), 5160.
45. Allen, H. C.; Raymond, E. A.; Richmond, G. L. Surface structural studies of methane sulfonic acid at air/aqueous solution interfaces using vibrational sum frequency spectroscopy. J. Phys. Chem. A 2001, 105 (9), 1649.
46. 2 surface: Probing the surface acidity with vibrational sum frequency generation spectroscopy. Environ. Sci. Technol. 2005, 39 (7), 2025.
47. Venables, J. A. Introduction to Surface and Thin Film Processes; Cambridge University Press: Cambridge, UK, 2000.
48. Sahai, N. Is silica really an anomalous oxide? Surface acidity and aqueous hydrolysis revisited. Environ. Sci. Technol. 2002, 36 (3), 445.
49. Dines, T. J.; MacGregor, L. D.; Rochester, C. H. The surface acidity of oxides probed by IR spectroscopy of adsorbed diazines. Phys. Chem. Chem. Phys. 2001, 3 (13), 2676.
50. a prediction: Critical reanalysis and a new approach. Geochim. Cosmochim. Acta 2004, 68 (9), 2025.
51. Ong, S.; Zhao, X.; Eisenthal, K. B. Polarization of water molecules at a charged interface: Second harmonic studies of the silica/water interface. Chem. Phys. Lett. 1992, 191, 327.
52. Higgins, S. R.; Stack, A. G.; Knauss, K. G.; Eggleston, C.; Jordan, G. In Water-Rock Interactions, Ore Deposits, and Environmental Geochemistry: A Tribute to David A. Crerar; Hellmann, R. E., Ed.; The Geochemical Society: St Louis, MO, 2002, 7, 111.
53. Ma, G.; Liu, D.; Allen, H. C. Piperidine adsorption on hydrated α-alumina (0001) surface studied by vibrational sum frequency generation spectroscopy. Langmuir 2004, 20 (26), 11620.