Abstract
The mechanism of the Kolbe-Schmitt reaction of sodium 2-naphthoxide is examined by means of the B3LYP/LANL2DZ method. After the initial formation of sodium 2-naphthoxide-CO2 complex, the carbon of the CO2 moiety performs an electrophilic attack on the naphthalene ring. Further transformations lead to the formation of sodium 2-hydroxy-1-naphthoate. Sodium 3-hydroxy-2-naphthoate is formed by a 1,3-rearrangement of the CO2Na group. Our findings are in good agreement with the experimental results on the carboxylation reaction of sodium 2-naphthoxide.
Similar content being viewed by others
References
H Kolbe (1860) Liebigs Ann 113 125
R Schmitt (1885) J Prakt Chem 31 397 Occurrence Handle10.1002/prac.18850310130
IA Daives (1928) Z Phys Chem 134 57
Hales JL, Jones JI, Lindsey AS (1954) J Chem Soc:3145
AS Lindsey H Jeskey (1957) Chem Rev 57 583 Occurrence Handle10.1021/cr50016a001 Occurrence Handle1:CAS:528:DyaG1cXmtFGj
DC Ayres (1966) Carbanions in Synthesis Oldbourne Press London 168
MA Rahim Y Matsui Y Kosugi (2002) Bull Chem Soc Jpn 75 619 Occurrence Handle10.1246/bcsj.75.619 Occurrence Handle1:CAS:528:DC%2BD38Xit1Kgt70%3D
Y Kosugi Y Imaoka F Gotoh MA Rahim Y Matsui K Sakanishi (2003) Org Biomol Chem 1 817 Occurrence Handle10.1039/b210793g Occurrence Handle1:CAS:528:DC%2BD3sXjt1Ggtbc%3D
Z Marković JP Engelbrecht S Marković (2002) Z Naturforsch 57a 812
Z Marković S Marković N Begović (2006) J Chem Inf Model 46 1957 Occurrence Handle10.1021/ci0600556
I Stanescu RR Gupta LEK Achenie (2006) Mol Sim 32 279 Occurrence Handle10.1080/08927020600615000 Occurrence Handle1:CAS:528:DC%2BD28XntFWnsr0%3D
I Stanescu LEK Achenie (2006) Chem Eng Sci 61 6199 Occurrence Handle10.1016/j.ces.2006.05.025 Occurrence Handle1:CAS:528:DC%2BD28Xns1Gqtr0%3D
S Marković Z Marković N Begović N Manojlović (2007) Russ J Phys Chem 81 1392 Occurrence Handle10.1134/S0036024407090087
Z Marković S Marković N Manojlović J Predojević-Simović (2007) J Chem Inf Model 47 1520 Occurrence Handle10.1021/ci700068b
NF Silin NK Moschtschinkaja (1938) J Gen Chem USSR 8 810 Occurrence Handle1:CAS:528:DyaA1MXos12i
GI Gershzon (1944) Chem Abstracts 38 1219
GV Chelintsev LM Smorgonskii (1947) Chem Abstracts 41 5466
K Suenobu M Nagaoka T Yamabe (1999) J Mol Struct (Theochem) 461–462 581 Occurrence Handle10.1016/S0166-1280(98)00474-6
WJ Hehre AJ Shusterman WW Huang (1996) Laboratory Book of Computational Organic Chemistry Wavefunction Inc. Irvine
AD Becke (1988) Phys Rev A 38 3098 Occurrence Handle10.1103/PhysRevA.38.3098 Occurrence Handle1:CAS:528:DyaL1cXmtlOhsLo%3D
C Lee W Yang RG Parr (1988) Phys Rev B 37 785 Occurrence Handle10.1103/PhysRevB.37.785 Occurrence Handle1:CAS:528:DyaL1cXktFWrtbw%3D
AD Becke (1993) J Chem Phys 98 5648 Occurrence Handle10.1063/1.464913 Occurrence Handle1:CAS:528:DyaK3sXisVWgtrw%3D
MJ Frisch GW Trucks HB Schlegel GE Scuseria MA Robb JR Cheeseman VG Zakrzewski JA Montgomery SuffixJr RE Stratmann JC Burant S Dapprich JM Millam AD Daniels KN Kudin MC Strain O Farkas J Tomasi V Barone M Cossi R Cammi B Mennucci C Pomelli C Adamo S Clifford J Ochterski GA Petersson PY Ayala Q Cui K Morokuma AD Malick KD Rabuck K Raghavachari JB Foresman J Cioslowski JV Ortiz AG Baboul BB Stefanov G Liu A Liashenko P Piskorz I Komaromi R Gomperts RL Martin DJ Fox T Keith MA Al-Laham CY Peng A Nanayakkara M Challacombe PMW Gill B Johnson W Chen MW Wong JL Andres C Gonzalez M Head-Gordon ES Replogle JA Pople (1998) Gaussian 98, Revision A9 Gaussian Inc. Pittsburgh
McCoy JD, Nath SK (1996) In: Laird BB, Ross RB, Zeigler T (eds) Chemical Applications of Density Functional Theory. Am Chem Soc, Washington, p 246
JP Foster F Weinhold (1980) J Am Chem Soc 102 7211 Occurrence Handle10.1021/ja00544a007 Occurrence Handle1:CAS:528:DyaL3cXmtFSmsbw%3D
AE Reed RB Weinstock F Weinhold (1985) J Chem Phys 83 735 Occurrence Handle10.1063/1.449486 Occurrence Handle1:CAS:528:DyaL2MXltFSisLY%3D
G Schaftenaar (1988) MOLDEN 3.7 CAOS/CAMM Center Netherland
Author information
Authors and Affiliations
Corresponding author
Additional information
Correspondence: Svetlana Marković, Faculty of Science, University of Kragujevac, 34000 Kragujevac, Serbia
Rights and permissions
About this article
Cite this article
Marković, Z., Marković, S. & Đurović, I. Kolbe-Schmitt reaction of sodium 2-naphthoxide. Monatsh Chem 139, 329–335 (2008). https://doi.org/10.1007/s00706-007-0771-6
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s00706-007-0771-6