On hydrogen bonding in 2-amino-3-hydroxymethyl-1,3-propane diol (TRIS) - Variable temperature neutron single crystal and DFT study

Zeitschrift fur Kristallographie

Volumn 222, Issue 10, 2007, Pages 555-565

  Smrčok, L'ubomír ^a   Piccoli, Paula M Briggs ^b   Schultz, Arthur J ^b   Sládkovičová, Mariana ^a   Mach, Pavel ^a  

^a INSTITUTE OF CHEMISTRY   (Slovakia)

^b ARGONNE NATIONAL LABORATORY   (United States)

Author keywords

DFT; Neutron diffraction; Single crystal structure analysis; Tris(hydroxymethyl) aminomethane

Indexed keywords

EID: 35648973149     PISSN: 00442968     EISSN: None     Source Type: Journal    
DOI: 10.1524/zkri.2007.222.10.555     Document Type: Article

References (54)

1. Bates, R. G.; Robinson, R. A.: Tris(hydroxymethyl)aminomethane. Useful secondary pH standard. Anal. Chem. 45 (1973) 420-420.
2. Blöchl, P. E.: Projector augmented-wave method. Phys. Rev. B50 (1994) 17953-17979.
3. Brandenburg, K.: Diamond. Version 3.1d. Crystal Impact GbR, Bonn, Germany, (2006).
4. Bruno, I. J.; Cole, J. C.; Edgington, P. R.; Kessler, M.; Macrae, C. F.; McCabe, P.; Pearson, J.; Taylor, R.: New software for searching the Cambridge Structural Database and visualizing crystal structures. Acta Cryst. B58 (2002) 389-397.
5. Calhorda, M. J.: Weak hydrogen bonds: theoretical studies. Chem. Commun. (2000) 801-809.
6. Castellari, C.; Ottani, S.: Anti-Inflammatory Drugs. V. [Tris-(2-hydroxymethyl)methyl]ammonium 2-[(2,6-Dichlorophenyl)amino] phenylacetate (TRISH. D). Acta Cryst. C53 (1997) 482-486.
7. Castenada, J. P.; Denisov, G. S.; Kucherov, S. Yu.; Schreiber, V. M.; Shurukina, A. V.: Infrared and ab initio studies of hydrogen bonding and proton transfer in the complexes formed by pyrazoles. J. Molecular Structure 660 (2003) 25-40.
8. Debrus, S.; May, M.; Barycki, J.; Glowiak, T.; Barnes, A. J.; Rtajczak, H.; Xue, F.: Crystal structure, vibrational spectra and non-linear optical properties of the orthoarsenic acid-tris- (hydroxymethyl)- aminomethane crystal. J. Molecular Structure 661-662 (2004) 595-601.
9. Dunitz, J. D.; White, D. N.: Non-rigid-body thermal-motion analysis. J. Acta Cryst. A29 (1973) 93-94.
10. Ďurovič, S.; Kupčík, V.: Crystallographic data on Tris-hydroxymethyl-aminomethane. Chem. Zvesti 13 (1959) 565-571. In Slovak.
11. Eilerman, D.; Rudman, R.: Polymorphism of crystalline poly(hydroxymethyl) compounds. III. The structures of crystalline and plastic tris(hydroxymethyl) aminomethane. J. Chem. Phys. 72 (1980) 5656-5666.
12. Eilerman, D.; Rudman, R.: Structure of tris(hydroxymethyl) acetic acid. Acta Cryst. B35 (1979) 2768-2771.
13. Ejsmont, K.; Zaleski, J.; Joe, I. H.; Jayakumar, V. S.: Bis(glycyl-glycinium) oxalate at 100 K. Acta Cryst C59 (2003) o553-o555.
14. Farugia, L. J.: ORTEP-3 for Windows - a version of ORTEP-III with a Graphical User Interface (GUI). J. Appl. Cryst. 30 (1997) 565-565.
15. Farrugia, L. J.: WinGXsuite for small molecule single-crystal crystallography. J. Appl. Cryst. 32 (1999) 837-838.
16. Gatti, C.; May, E.; Destro, R.; Cargnoni, F.: Fundamental properties and nature of CH center dot center dot O interactions in crystals on the basis of experimental and theoretical charge densities. The case of 3,4- bis(dimethylamino)-3-cyclobutene-1,2-dione (DMACB) crystal. J. Phys. Chem. A106 (2002) 2707-2720.
17. Golovina, N. I.; Raevskii, A. V.; Fedorov, B. S.; Chukanov, N. V.; Shilov, G. V.; Keonova, L. S.; Tarasov, V. P.; Erofeev, L. N.: Temperature-dependent structure-energy changes in crystals of compounds with poly(hydroxymethyl) grouping. J. Solid State Chem. 164 (2002) 301-312.
18. Gu, Y.; Kar, T.; Scheiner, S.: Fundamental properties of the CH . . . O Interaction: Is it a true hydrogen bond? J. Am. Chem. Soc. 121 (1999) 9411-9422.
19. Hanuza, J.; Maczka, M.; Waskowska, A.; Oganowski, W.; Andruszkiewicz, M.; Ban-Oganowska, H.; Lutz, B.; van der Maas, J. H.: Structural and spectroscopic evidence of hydrogen bonding in 3-bromo-5-hydroxy-2,6-dimethylpyridine and 3-chloro-5-hydroxy-2,6-dimethylpyridine. J. Mol. Structure 404 (1997) 33-45.
20. Hirshfeld, F. L.: Can X-ray data distinguish bonding effects from vibrational smearing? Acta Cryst. A32 (1976) 239-244.
21. Howard, J. A. K.; Johnson, O.; Schultz, A. J.; Stringer, A. M.: Determination of the neutron absorption cross section for hydrogen as a function of wavelength with a pulsed neutron source. J. Appl. Cryst. 20 (1987) 120-122.
22. Ivarsson, G. J. M.: Structure of bis[tris(hydroxymethyl) aminomethane nickel(II) diperchlorate. Acta Cryst. B38 (1982) 1828-1831.
23. Jeffrey, G. A.: An Introduction to Hydrogen Bonding. Oxford University Press, 1997.
24. Kendi, E.: Molecular and crystal structure of tris(hydroxymethyl) aminomethane. Z. Kristallogr. 160 (1982) 139-143.
25. Kresse, G.; Hafner, J.: Ab initio molecular dynamics for open-shell transition metals. Phys. Rev. B48 (1993) 13115-13118.
26. Kresse, G.; Hafner, J.: Norm-conserving and ultrasoft pseudopotentials for first-row and transition elements. J. Phys. Condens. Matter 6 (1994) 8245-8527.
27. Kresse, G.; Furthmüller, J.: Efficiency of ab-initio total energy calculations for metals and semiconductors using a plane-wave basis set. Comp. Mat. Sci. 6 (1996) 15-50.
28. Kresse, G.; Joubert, D.: From ultrasoft pseudopotentials to the projector augmented-wave method. Phys. Rev. B59 (1999) 1758-1775.
29. Larson, A. C.; Von Dreele, R. B.: General Structure Analysis System-GSAS. Los Alamos National Laboratory, 2004.
30. Lautié, A.; Froment, F.; Novak, A.: Relationship between NH stretching frequencies and N . . . O distances of crystals containing NH . . . O bonds. Spectroscopy Letters 9 (1976) 289-299.
31. 2) hydrogen bond. Acta Cryst. (1992) B48 700-713.
32. Loehlin, J. H.; Franz, K. J.; Gist, L.; Moore, R. H.: Supramolecular alcohol-amine crystals and their hydrogen-bond patterns. Acta Cryst. B54 (1998) 695-704.
33. Perdew, J. P.; Wang, Y.: Accurate and simple analytic representation of the electron-gas correlation energy. Phys. Rev. B45 (1992) 13244-13249.
34. Ramette, R. W.; Culberson, C. H.: Acid-base properties of tris(hydroxymethyl)aminomethane (Tris) buffers in sea water from 5 to 40°C. Anal. Chem. 49 (1977) 867-870.
35. Rose, H. A.; Van Camp, A.: Tris(hydroxymethyl)aminomethane (2-amino-2-hydroxy-methyl-1,3-propanediol). Anal. Chem. 27 (1955) 1356.
36. Rudman, R.; Eilerman, D.; LaPlaca, S. J.: The structure of crystalline Tris: a plastic crystal precursor, buffer, and acetylcholine attenuator. Science 200 (1978) 531-533.
37. +X- (X=F, Cl, Br, I). Acta Cryst. C39 (1983) 1267-1271.
38. Rychlý, R.; Pekárek, V.: The use of potassium chloride and tris(hydroxymethyl)aminomethane as standard substances for solution calorimetry. J. Chem. Thermodynamics 9 (1977) 391-396.
39. Sears, V. F.: Methods of Experimental Physics. Vol. 23, Neutron Scattering, Part A. Academic Press: Orlando, FL, 1986; pp. 521-550.
40. Semmingsen, D.: Neutron diffraction refinement of the structure of pentaerythritol. Acta Chem. Scand. A42 (1988) 279-283.
41. Schmidt, M. W.; Baldridge, K. K.; Boatz, J. A.; Elbert, S. T.; Gordon, M. S.; Jenses, J. H.; Koseki, S.; Matsunaga, N.; Nguyen K. A.; Su, S.; Windus, T. L.; Dupuis, M.; Motgomery, J. A. Jr.: General atomic and molecular electronic structure system. J. Comput. Chem. 14 (1993) 1347-1363.
42. Schomacher, V.; Trueblood, K. N.: On the rigid-body motion of molecules in crystals. Acta Cryst. B24 (1968) 63-76.
43. Schultz, A. J.; Van Derveer, D. G.; Parker, D. W.; Baldwin, J. E.: Structure of methylenecyclopropane-2-carboxamide by time-of-flight neutron diffraction. Acta Cryst. C46 (1990) 276-279.
44. Schultz, A. J.; De Lurgio, P. M.; Hammonds, J. P.; Mikkelson, D. J.; Mikkelson, R. L.; Miller, M. E.; Naday, I.; Peterson, P. F.; Porter, R. R.; Worlton, T. G.: The upgraded IPNS single crystal diffractometer. Physica B385-386 (2006) 1059-1061.
45. Shakked, Z.; Viswamitra, M. A.; Kennard, O.: Interactions of Tris buffer with nucleotides: The crystal structure of tris(hydroxymethyl)methylamonium adenosine 5′-diphosphate dehydrate. Biochemistry 19 (1980) 2567-2571.
46. Sládkovičová, M.; Mach, P.; Smrčok, L.; Rundlof, H.: DFT and neutron diffraction study of 1,6-anhydro-β-D- glucopyranose (levoglucosan). Central European Journal of Chemistry 5 (2007a) 55-70.
47. Sládkovićová, M.; Smrčok, L.; Mach, P.; Tunega, D.; Ramirez-Cuesta, A. J.: Inelastic neutron scattering and DFT study of 1,6-anhydro-β-D-glucopyranose (levoglucosan). J. Molecular Structure 2007b. doi:10.1016/j.molstruc.2007.03.042
48. Sládkovičová, M.; Smrčok, L.; Mach, P.; Tunega, D.; Kolesnikov, A. I.: Inelastic neutron scattering and DFT study of 2-amino-3-hydroxymethyl-1,3-propane diol (TRIS). Chem. Phys. (2007c). Accepted.
49. Smrčok, L.; Sládkovicová, M.; Langer, V.; Wilson, C.C.; Koóš, M.: On hydrogen bonding in 1,6-anhydro-β-D- glucopyranose (levoglucosan) : X-ray and neutron diffraction and DFT study. Acta Cryst. B62 (2006) 912-918.
50. Spek, A. L.: Single-crystal structure validation with the program PLATON. J. Appl. Cryst. 36 (2003) 7-13.
51. Steiner, T.; Saenger, W.: Geometric analysis of non-ionic O-H . . . O hydrogen bonds and non-bonding arrangements in neutron diffraction study of carbohydrates. Acta Cryst. B48 (1992a) 819-827.
52. Steiner, T.; Saenger, W.: Geometry of C-H . . . O hydrogen bonds in carbohydrate crystal structures. Analysis of neutron diffraction data. J. Am. Chem. Soc. 114 (1992b) 10146-10154.
53. Steiner, T.; Saenger, W.: Lengthening of the covalent O-H bond in O-H . . . O hydrogen bonds re-examined from low-temperature neutron diffraction data of organic compounds. Acta Cryst. B50 (1994) 348-357.
54. Steiner, T.: The hydrogen bond in the solid state. Angew. Chem. Int. Ed. 41 (2002) 48-76.