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Application of Non-Linear Hammett Relationship to Surface Tensions and Dipole Moments in Estimating the Associative Behavior of Phenols: A Chemical Educational Article to Graduate Students
Corresponding Author(s) : V. Jagannadham
Asian Journal of Chemistry,
Vol. 27 No. 9 (2015): Vol 27 Issue 9
Abstract
Non-linear Hammett relationship was applied to surface tensions (g) and dipole moments (μ) of some meta and para substituted phenols. The non-linearity of log g versus Hammett s correlation was explained in terms of Eötvös constant, Ramsay-Shields equation, Trouton’s rule, order of association, sandwich type molecular pairs and number of hydrogen bond donor-acceptor sites (Had). And non-linearity of log μ versus Hammett s correlation was explained in terms of the net bulk property of the entire molecule and not based on a chemical property like a localized reaction center.
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- J. Hine, Structural effects on Equilibriums in Organic Chemistry, Wiley-Interscience, New York (1975).
- C.D. Johnson, The Hammett Equation, Cambridge University Press (1973).
- J. Shorter, Correlation Analysis in Organic Chemistry, Oxford University Press (1973).
- L.P. Hammett, Physical Organic Chemistry, McGraw-Hill, New York, edn 2 (1970).
- Besides these References there are Several Physical-Organic Chemistry Text Books which can be Referred in any University Libraries.
- L.P. Hammett, Chem. Rev., 17, 125 (1935); doi:10.1021/cr60056a010.
- J. O. Schreck, J. Chem. Educ., 48, 103 (1971); doi:10.1021/ed048p103.
- G.M. Santerre, C.J. Hansrote Jr. and T.I. Crowell, J. Am. Chem. Soc., 80, 1254 (1958); doi:10.1021/ja01538a056.
- H.H. Szmant and C. Harmuth, J. Am. Chem. Soc., 86, 2909 (1964); doi:10.1021/ja01068a028.
- R. Fuchs and D.M. Carlton, J. Am. Chem. Soc., 85, 104 (1963); doi:10.1021/ja00884a022.
- A. Naseeruddin, A.S. Ranganatha Swamy and V. Jagannadham, Indian J. Chem., 26A, 427 (1987).
- C.K. Hancock, J.N. Pawloski and J.P. Idoux, J. Org. Chem., 31, 3801 (1966); doi:10.1021/jo01349a073.
- C.K. Hancock and J.P. Idoux, J. Org. Chem., 32, 1931 (1967); doi:10.1021/jo01281a050.
- R. Sanjeev, V. Jagannadham and R.V. Vrath, Educ. J., 1, 1 (2012); doi:10.11648/j.edu.20120101.11.
- R. Sanjeev, V. Jagannadham, A. Adam and A. Das, World J. Chem. Educ., 2, 39 (2014); doi:10.12691/wjce-2-3-2.
- R. Sanjeev, V. Jagannadham and R.V. Vrath, World J. Chem. Educ., 1, 1 (2013); doi:10.12691/wjce-1-1-1.
- I.-H. Um, J.-Y. Lee, H.-T. Kim and S.-K. Bae, J. Org. Chem., 69, 2436 (2004); doi:10.1021/jo035854r.
- S. Fukuzumi and J.K. Kochi, J. Am. Chem. Soc., 103, 7240 (1981); doi:10.1021/ja00414a034.
- H.J. Koh, K.L. Han and I. Lee, J. Org. Chem., 64, 4783 (1999); doi:10.1021/jo990115p.
- E.A. Castro, J.G. Santos, J. Téllez and M.I. Umaña, J. Org. Chem., 62, 6568 (1997); doi:10.1021/jo970624w.
- I. Jmaoui, T. Boubaker and R. Goumont, Int. J. Chem. Kinet., 45, 152 (2013); doi:10.1002/kin.20751.
- I.-H. Um, K.-H. Kim, H.-R. Park, M. Fujio and Y. Tsuno, J. Org. Chem., 69, 3937 (2004); doi:10.1021/jo049694a.
- I.-H. Um, E.Y. Kim, H.-R. Park and S.-E. Jeon, J. Org. Chem., 71, 2302 (2006); doi:10.1021/jo052417z.
- I.-H. Um, H.-J. Han, J.-A. Ahn, S. Kang and E. Buncel, J. Org. Chem., 67, 8475 (2002); doi:10.1021/jo026339g.
- I.-H. Um, J.-Y. Hong, J.-J. Kim, O.-M. Chae and S.-K. Bae, J. Org. Chem., 68, 5180 (2003); doi:10.1021/jo034190i.
- I.-H. Um, S.-J. Hwang, M.-H. Baek and E.J. Park, J. Org. Chem., 71, 9191 (2006); doi:10.1021/jo061682x.
- M.J. Zdilla, J.L. Dexheimer and M.M. Abu-Omar, J. Am. Chem. Soc., 129, 11505 (2007); doi:10.1021/ja073027s.
- F. Effenberger, J.K. Eberhard and A.H. Maier, J. Am. Chem. Soc., 118, 12572 (1996); doi:10.1021/ja9624331.
- S. Shaik, Prog. Phys. Org. Chem., 15, 197 (1985); doi:10.1002/9780470171943.ch4.
- H.K. Oh, J.M. Lee, H.W. Lee and I. Lee, Int. J. Chem. Kinet., 36, 434 (2004); doi:10.1002/kin.20000.
- E. Buncel, C. Cannes, A.-P. Chatrousse and F. Terrier, J. Am. Chem. Soc., 124, 8766 (2002); doi:10.1021/ja020379k.
- F. Terrier, G. Moutiers, L. Xiao, E. Le Guevel and F. Guir, J. Org. Chem., 60, 1748 (1995); doi:10.1021/jo00111a037.
- M. Bonchio, S. Calloni, F. Di Furia, G. Licini, G. Modena, S. Moro and W.A. Nugent, J. Am. Chem. Soc., 119, 6935 (1997); doi:10.1021/ja9711371.
- R. Ravi, R. Sanjeev and V. Jagannadham, Int. J. Chem. Kinet., 45, 803 (2013); doi:10.1002/kin.20818.
- J.J. Jasper, J. Phys. Chem. Ref. Data, 1, 841 (1972); doi:10.1063/1.3253106.
- V. Majer and V. Svoboda, Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford (1985).
- H. Udin, A.J. Shaler and J. Wulff, J. Metal, 1, 186 (1949).
- http://en.wikipedia.org/wiki/Surface_energy.
- http://www.physics.usyd.edu.au/~et/shared/References/References%202008/Crystals/Shu ttleworth%20PPS63A%201950%20The%20Surface%20Tension%20of%20Solids.pdf.
- F.P. Parungo and J.P. Lodge Jr., J. Atmos. Sci., 22, 309 (1965); doi:10.1175/1520-0469(1965)022<0309:MSAINO>2.0.CO;2.
- J. Koudelka and O. Exner, Collect. Czech. Chem. Commun., 50, 188 (1985); doi:10.1135/cccc19850188.
- S. Sugden, J. Chem. Soc. Trans., 125, 32 (1924); doi:10.1039/ct9242500032.
- R. Eötvös, Ann. Phys., 263, 448 (1886); doi:10.1002/andp.18862630309.
- F. Trouton, Philosophical Magazine Series, 18, 54 (1884); doi:10.1080/14786448408627563.
- O. Exner, Dipole Moments in Organic Chemistry, Georg Theime Publishers, Stuttgart (1975).
- Benzene - Wikipedia, the free encyclopedia en.wikipedia.org/wiki/Benzene
- J. March, Advanced Organic Chemistry: Reactions, Mechanisms and Structure, Wiley Interscience Publication, John Wiley & Sons, p. 16 (1992).
References
J. Hine, Structural effects on Equilibriums in Organic Chemistry, Wiley-Interscience, New York (1975).
C.D. Johnson, The Hammett Equation, Cambridge University Press (1973).
J. Shorter, Correlation Analysis in Organic Chemistry, Oxford University Press (1973).
L.P. Hammett, Physical Organic Chemistry, McGraw-Hill, New York, edn 2 (1970).
Besides these References there are Several Physical-Organic Chemistry Text Books which can be Referred in any University Libraries.
L.P. Hammett, Chem. Rev., 17, 125 (1935); doi:10.1021/cr60056a010.
J. O. Schreck, J. Chem. Educ., 48, 103 (1971); doi:10.1021/ed048p103.
G.M. Santerre, C.J. Hansrote Jr. and T.I. Crowell, J. Am. Chem. Soc., 80, 1254 (1958); doi:10.1021/ja01538a056.
H.H. Szmant and C. Harmuth, J. Am. Chem. Soc., 86, 2909 (1964); doi:10.1021/ja01068a028.
R. Fuchs and D.M. Carlton, J. Am. Chem. Soc., 85, 104 (1963); doi:10.1021/ja00884a022.
A. Naseeruddin, A.S. Ranganatha Swamy and V. Jagannadham, Indian J. Chem., 26A, 427 (1987).
C.K. Hancock, J.N. Pawloski and J.P. Idoux, J. Org. Chem., 31, 3801 (1966); doi:10.1021/jo01349a073.
C.K. Hancock and J.P. Idoux, J. Org. Chem., 32, 1931 (1967); doi:10.1021/jo01281a050.
R. Sanjeev, V. Jagannadham and R.V. Vrath, Educ. J., 1, 1 (2012); doi:10.11648/j.edu.20120101.11.
R. Sanjeev, V. Jagannadham, A. Adam and A. Das, World J. Chem. Educ., 2, 39 (2014); doi:10.12691/wjce-2-3-2.
R. Sanjeev, V. Jagannadham and R.V. Vrath, World J. Chem. Educ., 1, 1 (2013); doi:10.12691/wjce-1-1-1.
I.-H. Um, J.-Y. Lee, H.-T. Kim and S.-K. Bae, J. Org. Chem., 69, 2436 (2004); doi:10.1021/jo035854r.
S. Fukuzumi and J.K. Kochi, J. Am. Chem. Soc., 103, 7240 (1981); doi:10.1021/ja00414a034.
H.J. Koh, K.L. Han and I. Lee, J. Org. Chem., 64, 4783 (1999); doi:10.1021/jo990115p.
E.A. Castro, J.G. Santos, J. Téllez and M.I. Umaña, J. Org. Chem., 62, 6568 (1997); doi:10.1021/jo970624w.
I. Jmaoui, T. Boubaker and R. Goumont, Int. J. Chem. Kinet., 45, 152 (2013); doi:10.1002/kin.20751.
I.-H. Um, K.-H. Kim, H.-R. Park, M. Fujio and Y. Tsuno, J. Org. Chem., 69, 3937 (2004); doi:10.1021/jo049694a.
I.-H. Um, E.Y. Kim, H.-R. Park and S.-E. Jeon, J. Org. Chem., 71, 2302 (2006); doi:10.1021/jo052417z.
I.-H. Um, H.-J. Han, J.-A. Ahn, S. Kang and E. Buncel, J. Org. Chem., 67, 8475 (2002); doi:10.1021/jo026339g.
I.-H. Um, J.-Y. Hong, J.-J. Kim, O.-M. Chae and S.-K. Bae, J. Org. Chem., 68, 5180 (2003); doi:10.1021/jo034190i.
I.-H. Um, S.-J. Hwang, M.-H. Baek and E.J. Park, J. Org. Chem., 71, 9191 (2006); doi:10.1021/jo061682x.
M.J. Zdilla, J.L. Dexheimer and M.M. Abu-Omar, J. Am. Chem. Soc., 129, 11505 (2007); doi:10.1021/ja073027s.
F. Effenberger, J.K. Eberhard and A.H. Maier, J. Am. Chem. Soc., 118, 12572 (1996); doi:10.1021/ja9624331.
S. Shaik, Prog. Phys. Org. Chem., 15, 197 (1985); doi:10.1002/9780470171943.ch4.
H.K. Oh, J.M. Lee, H.W. Lee and I. Lee, Int. J. Chem. Kinet., 36, 434 (2004); doi:10.1002/kin.20000.
E. Buncel, C. Cannes, A.-P. Chatrousse and F. Terrier, J. Am. Chem. Soc., 124, 8766 (2002); doi:10.1021/ja020379k.
F. Terrier, G. Moutiers, L. Xiao, E. Le Guevel and F. Guir, J. Org. Chem., 60, 1748 (1995); doi:10.1021/jo00111a037.
M. Bonchio, S. Calloni, F. Di Furia, G. Licini, G. Modena, S. Moro and W.A. Nugent, J. Am. Chem. Soc., 119, 6935 (1997); doi:10.1021/ja9711371.
R. Ravi, R. Sanjeev and V. Jagannadham, Int. J. Chem. Kinet., 45, 803 (2013); doi:10.1002/kin.20818.
J.J. Jasper, J. Phys. Chem. Ref. Data, 1, 841 (1972); doi:10.1063/1.3253106.
V. Majer and V. Svoboda, Enthalpies of Vaporization of Organic Compounds: A Critical Review and Data Compilation, Blackwell Scientific Publications, Oxford (1985).
H. Udin, A.J. Shaler and J. Wulff, J. Metal, 1, 186 (1949).
http://en.wikipedia.org/wiki/Surface_energy.
http://www.physics.usyd.edu.au/~et/shared/References/References%202008/Crystals/Shu ttleworth%20PPS63A%201950%20The%20Surface%20Tension%20of%20Solids.pdf.
F.P. Parungo and J.P. Lodge Jr., J. Atmos. Sci., 22, 309 (1965); doi:10.1175/1520-0469(1965)022<0309:MSAINO>2.0.CO;2.
J. Koudelka and O. Exner, Collect. Czech. Chem. Commun., 50, 188 (1985); doi:10.1135/cccc19850188.
S. Sugden, J. Chem. Soc. Trans., 125, 32 (1924); doi:10.1039/ct9242500032.
R. Eötvös, Ann. Phys., 263, 448 (1886); doi:10.1002/andp.18862630309.
F. Trouton, Philosophical Magazine Series, 18, 54 (1884); doi:10.1080/14786448408627563.
O. Exner, Dipole Moments in Organic Chemistry, Georg Theime Publishers, Stuttgart (1975).
Benzene - Wikipedia, the free encyclopedia en.wikipedia.org/wiki/Benzene
J. March, Advanced Organic Chemistry: Reactions, Mechanisms and Structure, Wiley Interscience Publication, John Wiley & Sons, p. 16 (1992).