An in-silico study of solvent effects on the Kolbe–Schmitt reaction using a DFT method

References

• Chren , M.M. and Bickers , D.R. 1990 . “ Dermatological pharmacology ” . In Pharmacological Basis of Therapeutics , Edited by: Goodman and Gilman . 1587 New York : Pergamon press .
   Google Scholar
• Reynolds , J.E.F. , ed. 1996 . “ Salicylic acid ” . In Martindale The Extra Pharmacopoeia , 31 , 1093 London : The Royal Pharmaceutical Society .
   Google Scholar
• Windholz , M. 1983 . “ Salicylic acid ” . In The Merck Index , 10 , 8190 Rahway, NJ, USA : Merck & Co Inc .
   Google Scholar
• http://en.wikipedia.org/wiki/salicylate .
   Google Scholar
• Lindsey , A.S. and Jeskey , H. 1957 . The Kolbe–Schmitt reaction . Chem. Rev. , 57 : 583
   Web of Science ®Google Scholar
• Kolbe , H. 1860 . Ueber synthese der salicylsaure . Annales , 113 : 125
   Google Scholar
• T. Rieckmann. Salicylic acid. Fachhochschule Köln, University of Applied Sciences Cologne, Department of Plant Design and Chemical Engineering, MEng/reaction kinetics ( www.av.fh-koeln.de/professoren/rieckmann/chemischeprozesstechnik/lab_na-phenolate/na-phenolate.html ) (2004).
   Google Scholar
• Schmitt , R. 1885 . Beitrag zur kenntniss der Kolbe'schen salicyl–saure-synthese . J. Prakt. Chem. , 31 : 397
   Google Scholar
• Baine , O. , Adamson , G.F. , Barton , J.W. , Fitch , J.L. , Swayampati , D.R. and Jeskey , H. 1954 . The Kolbe–Schmitt reaction. II. The carbonation of phenols . J. Org. Chem. , 19 : 510
   Web of Science ®Google Scholar
• Ullmann's Encyclopedia of Industrial Chemistry . 1997 . Weinheim, Germany : Wiley-VCH .
   Google Scholar
• Hessler , J.C. 1907 . Some recent work in organic chemistry . J. Am. Chem. Soc. , 29 ( 1 ) : 88
   Google Scholar
• Tijmstra , S. and Lobry de Bruyn , C.A. 1904 . Rec. Trav. Chim. , 23 : 385
   Google Scholar
• Johnson , J.R. 1933 . Abnormal reactions of benzylmagnesium chloride. II. The mechanism of the o-tolyl rearrangement . J. Am. Chem. Soc. , 55 : 3029
   Google Scholar
• Luttringhaus , A. 1945 . Annales , 557 : 36
   Google Scholar
• Gilman , H. , Arntzen , C.E. and Webb , F.J. 1945 . Organometallic compounds in the Kolbe and Reimer–Tiemann reactions . J. Org. Chem. , 10 : 374
   Web of Science ®Google Scholar
• Hales , J.L. , Jones , J.I. and Lindsey , A.S. 1954 . Mechanism of Kolbe–Schmitt reaction . Chem. Ind. , 49 Hales, J.L., Jones, J.I., Lindsey, A.S., (1954). Mechanism of the Kolbe–Schmitt reaction. I. Infrared studies. J. Am. Chem. Soc., Abstracts
   Google Scholar
• Ayres , D.C. 1966 . “ Carbanions in synthesis ” . 168 – 173 . London : Oldbourne Press .
   Google Scholar
• Kunert , M. , Dinjus , E. , Nauck , M. and Sieler , J. 1997 . Structure and reactivity of sodium phenoxide. Following the course of the Kolbe–Schmitt reaction . Chem. Ber./Recl. , 130 ( 10 ) : 1461
   Google Scholar
• Kosugi , Y. , Imaoka , Y. , Gotoh , F. , Rahim , M.A. , Matsui , Y. and Sakanishi , K. 2003 . Carboxylations of alkali metal phenoxides with carbon dioxide . Org. Biomol. Chem. , 1 : 817
   PubMed Web of Science ®Google Scholar
• Markovic , Z. , Engelbrecht , J.P. and Markovic , S. 2002 . Theoretical study of the Kolbe–Schmitt reaction mechanism . Z. Naturforsch , 57 ( 9–10 ) : 812
   Google Scholar
• Frisch , M.J. , Trucks , G.W. , Schlegel , H.B. , Scuseria , G.E. , Robb , M.A. , Cheeseman , J.R. , Zakrzewski , V.G. , Montgomery , J.A. Jr , Stratmann , R.E. , Burant , J.C. , Dapprich , S. , Millam , J.M. , Daniels , A.D. , Kudin , K.N. , Strain , M.C. , Farkas , O. , Tomasi , J. , Barone , V. , Cossi , M. and Cammi , R. 1998 . Gaussian 98, Revision A.9 , Pittsburgh, PA : Gaussian, Inc . B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G.A. Petersson, P.Y. Ayala, Q. Cui, K. Morokuma, A.D. Malick, K.D. Rabuck, K. Raghavachari, J.B. Foresman, J. Cioslowski, J.V. Ortiz, A.G. Baboul, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C.Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, J.L. Andres, C. Gonzalez, M. Head-Gordon, E.S. Replogle, J.A. Pople
   Google Scholar
• I. Stanescu, L.E.K. Achenie (2005) A theoretical study of solvent effects on Kolbe–Schmitt reaction kinetics (submitted to Chemical Engineering Science).
   Google Scholar
• Jaguar 4.2 . 19912002 . “ Schrodinger ” . Portland, OR : LLC .
   Google Scholar
• Hay , P.J. and Wadt , W.R. 1985 . J. Chem. Phys. , 82 : 270 Hay, P.J. and Wadt, W.R., (1985) J. Chem. Phys. 82, 284
   Web of Science ®Google Scholar
• Moseley , J.C. , Edyvean , W. and Hartley , J. Aromatic hydroxy carboxylic acids . 1955 . (“Shell” Refining & Marketing Co., Ltd.)British Patent 738,359
   Google Scholar
• Ueno , R. and Tetsuya , N. Process for the production of p-hydroxybenzoic acid . (Ueno Pharmaceutical Co.)US Patent 3,816,521 . 1974 .
   Google Scholar
• Wacker , A. Manufacture of aromatic oxy-carboxylic acids . British Patent 384,619 . 1932 .
   Google Scholar
• >Dow Chemical Co . Salicylic acid and its alkali metal salts . British Patent 949,988 . 1964 .
   Google Scholar
• Jansen , G. and Wolff , P. Chemical process . US Patent 4,376,867 . 1983 .
   Google Scholar
• Barkley , L.B. Carboxylation of phenols . (Monsanto Chemical Co.)US Patent 2,824,892 . 1958 .
   Google Scholar
• Hirao , I. , Ota , K. , Sueta , S. and Hara , Y. 1967 . Carboxylation of phenol derivatives. IV. Synthesis of p-hydroxybenzoic acid and salicylic acid from alkali phenoxides in N,N-dimethylformamide . Yuki Gosei Kagaku Kyokaishi , 25 ( 5 ) : 412
   Google Scholar
• Furuya , M. , Nagatomo , A. and Wada , M. Preparation of hydroxybenzoic acids . (Mitsui Toatsu Chemicals, Inc., Japan)European Patent 834,494 A1 . 1998 .
   Google Scholar
• Wideqvist , S. 1954 . Some aspects of Kolbe's synthesis of salicylic acid . Ark. Kemi , 7 ( 26 ) : 229
   Google Scholar
• Fry , D.J. Hydroxy aromatic carboxylic acids . (Ilford Ltd.)British Patent 638,196 . 1950 .
   Google Scholar
• Gani , R. , Nielsen , B. and Fredenslund , A. 1991 . A group contribution approach to computer-aided molecular design . AIChE J. , 37 ( 9 ) : 1318
   Web of Science ®Google Scholar
• Venkatasubramanian , V. , Chan , K. and Caruthers , J.M. 1994 . Computer-aided molecular design using genetic algorithms . Comput. Chem. Eng. , 18 ( 9 ) : 833
   Web of Science ®Google Scholar
• Constantinou , L. , Bagherpour , K. , Gani , R. , Klein , J.A. and Wu , D.T. 1996 . Computer aided product design: problem formulations, methodology and applications . Comput. Chem. Eng. , 20 : 685
   Web of Science ®Google Scholar
• Duvedi , A.P. and Achenie , L.E.K. 1996 . Designing environmentally safe refrigerants using mathematical programming . Chem. Eng. Sci. , 51 ( 15 ) : 3727
   Web of Science ®Google Scholar
• Churi , N. and Achenie , L.E.K. 1996 . Novel mathematical programming model for computer aided molecular design . Ind. Eng. Chem. Res. , 35 ( 10 ) : 3788
   Web of Science ®Google Scholar
• Marcoulaki , E.C. and Kokossis , A.C. 1998 . Molecular design synthesis using stochastic optimisation as a tool for scoping and screening . Comput. Chem. Eng. , 22 : S11
   Web of Science ®Google Scholar
• Harper , P.M. and Gani , R. 2000 . A multi-step and multi-level approach for computer aided molecular design . Comput. Chem. Eng. , 24 : 677
   Web of Science ®Google Scholar
• Wang , Y. and Achenie , L.E.K. 2002 . Computer aided solvent design for extractive fermentation . Fluid Phase Equilib. , 201 ( 1 ) : 1
   Web of Science ®Google Scholar
• R. Gani. ICAS documentation. Computer Aided Process Engineering Center. Department of Chemical Engineering. Technical University of Denmark, Lyngby, Denmark (1999–2004).
   Google Scholar
• Barra , J. , Pena , M.A. and Bustamante , P. 2000 . Proposition of group molar constants for sodium to calculate the partial solubility parameters of sodium salts using the van Krevelen group contribution method . Eur. J. Pharm. Sci. , 10 : 153
   PubMed Web of Science ®Google Scholar
• Barton , A.F.M. 1991 . CRC Handbook of Solubility Parameters and Other Cohesion Parameters , 2 , Boca Raton, FL : CRC Press .
   Google Scholar
• Tannor , D.J. , Marten , B. , Murphy , R.B. , Friesner , R.A. , Sitkoff , D. , Nicholls , A. , Ringnalda , M.N. , Goddard , W.A. III and Honig , B. 1994 . Accurate first principles calculation of molecular charge distributions and solvation energies from ab initio quantum mechanics and continuum dielectric theory . J. Am. Chem. Soc. , 116 : 11875
   Web of Science ®Google Scholar
• Marten , B. , Kim , K. , Cortis , C. , Friesner , R.A. , Murphy , R.B. , Ringnalda , M.N. , Sitkoff , D. and Honig , B. 1996 . New model for calculation of solvation free energies: correction of self-consistent reaction field continuum dielectric theory for short-range hydrogen-bonding effects . J. Phys. Chem. , 100 : 11775
   Web of Science ®Google Scholar