Influence of water content on basicities in acetonitrile

Journal of Solution Chemistry

Volumn 43, Issue 7, 2014, Pages 1270-1281

  Kaupmees, Karl ^a   Kaljurand, Ivari ^a   Leito, Ivo ^a  

^a UNIVERSITY OF TARTU   (Estonia)

Author keywords

Charge delocalization; COSMO RS; Non aqueous solvent; pK a< inf>; Water residue

Indexed keywords

EID: 84920195353     PISSN: 00959782     EISSN: None     Source Type: Journal    
DOI: 10.1007/s10953-014-0201-4     Document Type: Article

References (25)

1. Reichardt, C.; Welton, T.: Solvents and Solvent Effects in Organic Chemistry, 3rd edn. Wiley-VCH, Weinheim (2011)
2. Katritzky, A.R.; Tamm, T.; Wang, Y.; Karelson, M.: A unified treatment of solvent properties. J. Chem. Inf. Comput. Sci. 39, 692-698 (1999)
3. Kaupmees, K.; Kaljurand, I.; Leito, I.: Influence of water content on the acidities in acetonitrile. Quantifying charge delocalization in anions. J. Phys. Chem. A 114, 11788-11793 (2010)
4. Espinosa, S.; Bosch, E.; Rosés, M.: Acid-base constants of neutral bases in acetonitrile-water mixtures. Anal. Chim. Acta 454, 157-166 (2002)
5. Buckenmaier, S.M.C.; McCalley, D.V.; Euerby, M.R.: Determination of pK(a) values of organic bases in aqueous acetonitrile solutions using capillary electrophoresis. J. Chromatogr. A 1004, 71-79 (2003)
6. Ahmed, I.T.; Soliman, E.S.; Boraei, A.A.A.: The acidity constants of some pyrimidine bases in various water-organic solvent media. Ann. Chim.-Rome 94, 847-856 (2004)
7. Kaljurand, I.; Rodima, T.; Leito, I.; Koppel, I.; Schwesinger, R.: Self-consistent spectrophotometric basicity scale in acetonitrile covering the range between pyridine and DBU. J. Org. Chem. 65, 6202-6208 (2000)
8. Kaljurand, I.; Kütt, A.; Sooväli, L.; Rodima, T.; Mäemets, V.; Leito, I.; Koppel, I.A.: Extension of the self-consistent spectrophotometric basicity scale in acetonitrile to a full span of 28 pK(a) units: unification of different basicity scales. J. Org. Chem. 70, 1019-1028 (2005)
9. Kaljurand, I.; Koppel, I.A.; Kütt, A.; Rõõm, E.-I.; Rodima, T.; Koppel, I.; Mishima, M.; Leito, I.: Experimental gas-phase basicity scale of superbasic phosphazenes. J. Phys. Chem. A 111, 1245-1250 (2007)
10. Rõõm, E.-I.; Kütt, A.; Kaljurand, I.; Koppel, I.; Leito, I.; Koppel, I.A.; Mishima, M.; Goto, K.; Miyahara, Y.: Brönsted basicities of diamines in the gas phase, acetonitrile, and tetrahydrofuran. Chem. Eur. J. 13, 7631-7643 (2007)
11. Eckert-Maksić, M.; Glasovac, Z.; Trošelj, P.; Kütt, A.; Rodima, T.; Koppel, I.; Koppel, I.A.: Basicity of guanidines with heteroalkyl side chains in acetonitrile. Eur. J. Org. Chem. 30, 5176-5184 (2008)
12. Kunetskiy, R.A.; Polyakova, S.M.; Vavrik, J.; Cisarova, I.; Saame, J.; Nerut, E.R.; Koppel, I.; Koppel, I.A.; Kütt, A.; Leito, I.; Lyapkalo, I.M.: A new class of organosuperbases, N-alkyl-and N-aryl-1,3-dialkyl-,4,5-dimethylimidazol-2-ylidene amines: synthesis, structure, pK BH+ measurements and properties. Chem. Eur. J. 18, 3621-3630 (2012)
13. Štrukil, V.; Eilović, I.; Matković-Čalogović, D.; Saame, J.; Leito, I.; Šket, P.; Plavec, J.; Eckert-Maksić, M.: Molecular structure and acid/base properties of 1,2-dihydro-1,3,5-triazine derivatives. New J. Chem. 36, 86-96 (2012)
14. Kaljurand, I.; Lilleorg, R.; Murumaa, A.; Mishima, M.; Burk, P.; Koppel, I.; Koppel, I.A.; Leito, I.: The basicity of substituted N, N-dimethylanilines in solution and in the gas phase. J. Phys. Org. Chem. 26, 171-181 (2013)
15. Haav, K.; Saame, J.; Kütt, A.; Leito, I.: Basicity of phosphanes and diphosphanes in acetonitrile. Eur. J. Org. Chem. 11, 2167-2172 (2012)
16. Marcus, Y.; Kamlet, M.J.; Taft, R.W.: Linear solvation energy relationships - Standard molar Gibbs free energies and enthalpies of tranfer of ions from water into nonaqueous solvents. J. Phys. Chem. 92, 3613-3622 (1988)
17. Marenich, A.V.; Kelly, C.P.; Thompson, J.D.; Hawkins, G.D.; Chambers, C.C.; Giesen, D.J.; Winget, P.; Cramer, C.J.; Truhlar, D.G.: Minnesota Solvation Database - version 2012. University of Minnesota, Minneapolis (2012)
18. Klamt, A.: COSMO-RS: From Quantum Chemistry to Fluid Phase Thermodynamics and Drug Design. Elsevier Science Ltd.; Amsterdam (2005)
19. MacDonald, S.M.; Opallo, M.; Klamt, A.; Eckert, F.; Marken, F.: Probing carboxylate Gibbs transfer energies via liquid vertical bar liquid transfer at triple phase boundary electrodes: ion-transfer voltammetry versus COSMO-RS predictions. Phys. Chem. Chem. Phys. 10, 3925-3933 (2008)
20. Klamt, A.; Schüürmann, G.: COSMO - A new approach to dielectric screening insolvents with explicit expressions for the screening energy and its gradient. J. Chem. Soc. Perkins Trans. 2(5), 799-805 (1993)
21. Kruve, A.; Kaupmees, K.; Liigand, J.; Leito, I.: Negative electrospray ionization via deprotonation: predicting the ionization efficiency. Anal. Chem. 86, 4822-4830 (2014)
22. Eckert, F.; Klamt, A. COSMOtherm, Version C3.0, Revision 12.01, COSMOlogic GmbH & CoKG: Leverkusen, Germany, 2011, http://www.cosmologic.de
23. Ahlrichs, R.; Bär, M.; Baron, H.-P.; Bauernschmitt, R.; Böcker, S.; Ehrig, M.; Eichkorn, K.; Elliott, S.; Furche, F.; Haase, F.; Häser, M.; Horn, H.; Hattig, C.; Huber, C.; Huniar, U.; Kattannek, M.; Köhn, M.; Kölmel, C.; Kollwitz, M.; May, K.; Ochsenfeld, C.; Öhm, H.; Schäfer, A.; Schneider, U.; Treutler, O.; von Arnim, M.; Weigend, F.; Weis, P.; Weiss, H.: TURBOMOLE V6.2 2010, a development of University of Karlsruhe and Forschungszentrum Karlsruhe GmbH, 1989-2007, TURBOMOLE GmbH, since 2007. Available from http://www.turbomole.com
24. Eckert, F.; Leito, I.; Kaljurand, I.; Kütt, A.; Klamt, A.; Diedenhofen, M.: Prediction of acidity in acetonitrile solution with COSMO-RS. J. Comput. Chem. 30, 799-810 (2009)
25. Hall Jr.; H.K.: Correlation of the base strengths of amines. J. Am. Chem. Soc. 79, 5441-5444 (1957)