PL EN


Preferences help
enabled [disable] Abstract
Number of results
Journal
2013 | 11 | 11 | 1711-1722
Article title

A theoretical study of the limits of the acidity of carbon acids in phase transfer catalysis in water and in liquid ammonia

Content
Title variants
Languages of publication
EN
Abstracts
EN
The acidities of a large number of carbon acids have been theoretically calculated for the gas-phase and for DMSO solution. The gas-phase values, both ΔH and ΔG, are very well correlated with the available experimental data. From the calculated ΔG values in DMSO and the pKas in the same solvent, a homogeneous set of pK a (DMSO) values was devised that was used to generate pK a (water). These last pK as were used to establish the limits of the acidity of carbon acids for reactions under PTC conditions both alkylations and H/D exchange. A step further led to the pK as in liquid ammonia and from them to the virtual use of PTC using liquid ammonia instead of water. [...]
Keywords
Publisher

Journal
Year
Volume
11
Issue
11
Pages
1711-1722
Physical description
Dates
published
1 - 11 - 2013
online
25 - 8 - 2013
Contributors
author
  • Institute of Medical Chemistry, CSIC, E-28006, Madrid, Spain, ibon@iqm.csic.es
author
  • Institute of Medical Chemistry, CSIC, E-28006, Madrid, Spain
author
  • Institute of Medical Chemistry, CSIC, E-28006, Madrid, Spain
References
  • [1] C.M. Starks, C.L. Liotta, M. Halpern, Phase Transfer Catalysis, Fundamentals, Applications, and Industrial Perspectives (Chapman & Hall, New York, 1994) http://dx.doi.org/10.1007/978-94-011-0687-0[Crossref]
  • [2] R.A. Jones, Quaternary Ammonium Salts. Their Use in Phase-transfer Catalysis (Academic Press, London, 2001)
  • [3] A.G. Volkov, (Ed.), Interfacial Catalysis (Marcel Dekker, New York, 2003)
  • [4] K. Maruoka, Asymmetric Phase Transfer Catalysis (Wiley-VCH, Weinheim, 2008) http://dx.doi.org/10.1002/9783527622627[Crossref]
  • [5] M. Mąkosza, B. Serafin, Roczniki Chem. 39, 1401 (1965)
  • [6] M. Mąkosza, B. Serafin, Roczniki Chem. 39, 1595 (1965)
  • [7] M. Mąkosza, B. Serafin, T. Urbański, Chim. Ind. (Paris) 93, 537 (1965)
  • [8] M. Mąkosza, Pure Appl. Chem. 72, 1399 (2000) http://dx.doi.org/10.1351/pac200072071399[Crossref]
  • [9] M. Mąkosza, M. Fedoryński, Arkivoc iv, 7 (2006) http://dx.doi.org/10.3998/ark.5550190.0007.402[Crossref]
  • [10] C.M. Starks, J. Am. Chem. Soc. 93, 195 (1971) http://dx.doi.org/10.1021/ja00730a033[Crossref]
  • [11] A. Loupy, Ed. Microwaves in organic synthesis (Wiley-VCH, Weinheim, 2006)
  • [12] S.L. Regen, J. Am. Chem. Soc. 97, 5956 (1975) http://dx.doi.org/10.1021/ja00853a074[Crossref]
  • [13] S.L. Regen, J. Am. Chem. Soc. 98, 6270 (1976) http://dx.doi.org/10.1021/ja00436a034[Crossref]
  • [14] H.J.-M. Dou, R. Gallo, P. Hassanaly, J. Metzger, J. Org. Chem. 42, 4275 (1977) http://dx.doi.org/10.1021/jo00862a026[Crossref]
  • [15] A.K. Dillow, S.L.J. Yun, D. Suleiman, D.L. Boatright, C.L. Liotta, C.A. Eckert, Ind. Eng. Chem. Res. 35, 1801 (1996) http://dx.doi.org/10.1021/ie9600405[Crossref]
  • [16] K. Chandler, C.W. Culp, D.R. Lamb, C.L. Liotta, C.A. Eckert, Ind. Eng. Chem. Res. 37, 3252 (1998) http://dx.doi.org/10.1021/ie970741h[Crossref]
  • [17] A. Loris, A. Perosa, M. Selva, P. Tundo, J. Org. Chem. 68, 4046 (2003) http://dx.doi.org/10.1021/jo0268308[Crossref]
  • [18] W.S. Ryoo, Ph.D Thesis. Emulsions and Microemulsions of Water and Carbon Dioxide: Novel Surfactants and Stabilization Mechanisms (University of Texas at Austin, Austin, 2005)
  • [19] S. Thayumanavan, Patent EP1778614 A2, 2007
  • [20] F.G. Bordwell, Acc. Chem. Res. 21, 456 (1988) http://dx.doi.org/10.1021/ar00156a004[Crossref]
  • [21] J.J. Lagowski, Pure Appl. Chem. 25, 429 (1971) http://dx.doi.org/10.1351/pac197125020429[Crossref]
  • [22] P. Ji, N. Powles, J.H. Atherton, M.I. Page, Org. Lett. 13, 6118 (2011) http://dx.doi.org/10.1021/ol2026153[Crossref]
  • [23] A.D. Becke, Phys. Rev. A 38, 3098 (1988) http://dx.doi.org/10.1103/PhysRevA.38.3098[Crossref]
  • [24] C. Lee, W. Yang, R.G. Parr, Phys. Rev. B 37, 785 (1988) http://dx.doi.org/10.1103/PhysRevB.37.785[Crossref]
  • [25] R. Ditchfield, W.J. Hehre, J.A. Pople, J. Chem. Phys. 54, 724 (1971) http://dx.doi.org/10.1063/1.1674902[Crossref]
  • [26] M.J. Frisch, J.A. Pople, J.S. Binkley, J. Chem. Phys. 80, 3265 (1984) http://dx.doi.org/10.1063/1.447079[Crossref]
  • [27] S. Miertus, E. Scrocco, J. Tomasi, Chem. Phys. 55, 117 (1981) http://dx.doi.org/10.1016/0301-0104(81)85090-2[Crossref]
  • [28] J. Tomasi, M. Persico. Chem. Rev. 94, 2027 (1994) http://dx.doi.org/10.1021/cr00031a013[Crossref]
  • [29] R. Cammi, J. Tomasi, J. Comput. Chem. 16, 1449 (1995) http://dx.doi.org/10.1002/jcc.540161202[Crossref]
  • [30] M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, B. Mennucci, G.A. Petersson, H. Nakatsuji, M. Caricato, X. Li, H.P. Hratchian, A.F. Izmaylov, J. Bloino, G. Zheng, J.L. Sonnenberg, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, J.A. Montgomery, Jr., J.E. Peralta, F. Ogliaro, M. Bearpark, J.J. Heyd, E. Brothers, K.N. Kudin, V.N. Staroverov, R. Kobayashi, J. Normand, K. Raghavachari, A. Rendell, J.C. Burant, S.S. Iyengar, J. Tomasi, M. Cossi, N. Rega, J.M. Millam, M. Klene, J.E. Knox, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, R.L. Martin, K. Morokuma, V.G. Zakrzewski, G.A. Voth, P. Salvador, J.J. Dannenberg, S. Dapprich, A.D. Daniels, Ö. Farkas, J.B. Foresman, J.V. Ortiz, J. Cioslowski, D.J. Fox, Gaussian 09, Revision A.1 (Gaussian, Inc., Wallingford CT, 2009)
  • [31] P.J. Lindstrom, W.G. Mallard (Eds.), NIST Chemistry WebBook, NIST Standard Reference Database Number 69 (National Institute of Standards and Technology, USA, 2013)
  • [32] W.J. Hehre, L. Radom, P.v.R. Schleyer, J.A. Pople, Ab Initio Molecular Orbital Theory (John Wiley & Sons, New York, 1986) 411
  • [33] I. Alkorta, J. Elguero, Tetrahedron 53, 9741 (1997) http://dx.doi.org/10.1016/S0040-4020(97)00597-8[Crossref]
  • [34] M.C. Rezende, J. Braz. Chem. Soc. 12, 73 (2001) http://dx.doi.org/10.1590/S0103-50532001000100010[Crossref]
  • [35] I.A. Koppel, J. Koppel, V. Pihl, I. Leito, M. Mishima, V.M. Vlasov, L.M. Yagupolskii, R.W. Taft, J. Chem. Soc. Perkin 1125 (2000) [Crossref]
  • [36] A.M. Ross, D.L. Whalen, S. Eldin, R.M. Pollack, J. Am. Chem. Soc. 110, 1981 (1988) http://dx.doi.org/10.1021/ja00214a061[Crossref]
  • [37] Technical Bulletin Reaction Solvent Dimethyl Sulfoxide (DMSO) (Gaylor Chemical Corporation, USA, 2011) http://chemistry-chemists.com/N3_2011/U/DMSO-technical_bulletin.pdf
  • [38] F.G. Bordwell, J.E. Bartmess, J.A. Hautala, J. Org. Chem. 43, 3095 (1978) http://dx.doi.org/10.1021/jo00410a001[Crossref]
  • [39] W.P. Jencks, http://evans.harvard.edu/pdf/evans_pKa_table.pdf
  • [40] K. Shen, Y. Fu, J.-N. Li, L. Liu, Q.-X. Guo, Tetrahedron 63, 1568 (2007) http://dx.doi.org/10.1016/j.tet.2006.12.032[Crossref]
  • [41] F.G. Bordwell, Pure Appl. Chem. 49, 963 (1977) http://dx.doi.org/10.1351/pac197749070963[Crossref]
  • [42] I.E. Charif, S.M. Mekelleche, D. Villemin, N. Mora-Diez, J. Mol. Struct. THEOCHEM 818, 1 (2007) http://dx.doi.org/10.1016/j.theochem.2007.04.037[Crossref]
  • [43] Y. Chiang, A.J. Kresge, P.A. Walsh, J. Am. Chem. Soc. 108, 6314 (1986) http://dx.doi.org/10.1021/ja00280a032[Crossref]
  • [44] J.P. Guthrie, J. Cossar, Can. J. Chem. 64, 2470 (1986) http://dx.doi.org/10.1139/v86-407[Crossref]
  • [45] M.J. O’Donnell, W.D. Bennett, W.A. Bruder, W.N. Jacobsen, K. Knuth, B. LeClef, R.L. Polt, F.G. Bordwell, S.R. Mrozack, T.A. Cripe, J. Am. Chem. Soc. 110, 8250 (1988) http://dx.doi.org/10.1021/ja00232a056[Crossref]
  • [46] V.E. Matulis, Y.S. Halauko, O.A. Ivashkevich, P.N. Gaponik, J. Mol. Struct. THEOCHEM 909, 19 (2009) http://dx.doi.org/10.1016/j.theochem.2009.05.024[Crossref]
  • [47] Ionization Constants of Organic Acids. Ionization constants of carbon acids (Michigan State University, USA) http://www2.chemistry.msu.edu/faculty/reusch/virttxtjml/acidity2.htm
  • [48] A. Abbotto, S. Bradamante, G.A. Pagani, J. Org. Chem. 58, 449 (1993) http://dx.doi.org/10.1021/jo00054a031[Crossref]
  • [49] M. Hojatti, A.J. Kresge, W.-H. Wang, J. Am. Chem. Soc. 109, 4023 (1987) http://dx.doi.org/10.1021/ja00247a031[Crossref]
  • [50] J.P. Richard, G. Williams, J. Gao, J. Am. Chem. Soc. 121, 715 (1999) http://dx.doi.org/10.1021/ja982692l[Crossref]
  • [51] T. Bug, H. Mayr, J. Am. Chem. Soc. 125, 12980 (2003) http://dx.doi.org/10.1021/ja036838e[Crossref]
  • [52] G.I. Almerindo, D.W. Tondo, J.R. Pliego, J. Phys. Chem. A 108, 166 (2004) http://dx.doi.org/10.1021/jp0361071[Crossref]
  • [53] S. Rayne, K. Forest, Nature Precedings (2010) http://dx.doi.org/10.1038/npre.2010.4381.1 [Crossref]
  • [54] W.J. Spillane, P. Kavanagh, F. Young, H.J-M. Dou, J. Metzger, J. Chem. Soc. Perkin Trans. 1763 (1981)
  • [55] M. Mąkosza, M Fedorynski, Pol. J. Chem. 70, 1093 (1996)
  • [56] M. Mąkosza, Bull. Acad. Pol. Sci. 15, 165 (1967)
  • [57] M. Mąkosza, J. Przyborowski, R. Klajn, A. Kwast, Synlett 1773 (2000)
  • [58] M. Judka, A. Wojtasiewicz, W. Danikiewicz, M. Mąkosza, Tetrahedron 63, 8902 (2007) http://dx.doi.org/10.1016/j.tet.2007.06.014[Crossref]
  • [59] G.E. Hall, R. Piccolini, J.D. Roberts, J. Am. Chem. Soc. 77, 4540 (1955) http://dx.doi.org/10.1021/ja01622a033[Crossref]
  • [60] P. Ji, J. Atherton, M.I. Page, J. Org. Chem. 76, 1425 (2011) http://dx.doi.org/10.1021/jo102173k[Crossref]
  • [61] A. Sievers, R. Wolfenden, J. Am. Chem. Soc. 124, 13986 (2002) http://dx.doi.org/10.1021/ja021073g[Crossref]
  • [62] S. Sharma, J.K. Lee, J. Org. Chem. 69, 7018 (2004) http://dx.doi.org/10.1021/jo0303362[Crossref]
  • [63] E.V. Anslyn, D.A. Dougherty, Modern Physical Organic Chemistry (University Science Books, Sausalito, 2006)
  • [64] J.H. Takemoto, J.J. Lagowski, J. Am. Chem. Soc. 91, 3785 (1969) http://dx.doi.org/10.1021/ja01042a016[Crossref]
  • [65] B.G. Cox, Acids and Bases, Solvent Effects on Acid-Base Strength (Oxford University Press, Oxford, UK, 2013) 93 http://dx.doi.org/10.1093/acprof:oso/9780199670512.001.0001[Crossref]
  • [66] S. Julià, P. Sala, J. del Mazo, M. Sancho, C. Ochoa, J. Elguero, J.-P. Fayet, M.C. Vertut, J. Heterocycl. Chem. 19, 1141 (1982) http://dx.doi.org/10.1002/jhet.5570190531[Crossref]
  • [67] L. Avila, J. Elguero, S. Julià, J.M. del Mazo, Heterocycles 20, 1787 (1983) http://dx.doi.org/10.3987/R-1983-09-1787[Crossref]
  • [68] R.G. Pearson, R.L. Dillon, J. Am. Chem. Soc. 75, 2439 (1953) http://dx.doi.org/10.1021/ja01106a048[Crossref]
  • [69] J.R. Pliego, J.M. Riveros, J. Phys. Chem. A 106, 7434 (2002) http://dx.doi.org/10.1021/jp025928n[Crossref]
  • [70] M.C. Rezende, Tetrahedron 57, 5923 (2001) http://dx.doi.org/10.1016/S0040-4020(01)00563-4[Crossref]
  • [71] Y. Chiang, A.J. Kresge, J. Wirz, J. Am. Chem. Soc. 106, 6392 (1984) http://dx.doi.org/10.1021/ja00333a049[Crossref]
  • [72] Z. Wang (Ed.), Comprehensive Organic Name Reactions and Reagents (John Wiley & Sons, USA, 2009)
Document Type
Publication order reference
Identifiers
YADDA identifier
bwmeta1.element.-psjd-doi-10_2478_s11532-013-0311-7
JavaScript is turned off in your web browser. Turn it on to take full advantage of this site, then refresh the page.