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Volumn 1008, Issue , 2013, Pages 8-14

Theoretical study on the aminolysis of p-substituted phenyl acetates with dimeric ammonia in vacuo and acetonitrile

Author keywords

Aminolysis; CPCM; Phenyl acetate; Solvent effect; Substituent effect

Indexed keywords


EID: 84872671941     PISSN: 2210271X     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.comptc.2012.12.018     Document Type: Article
Times cited : (10)

References (39)
  • 1
    • 33947478659 scopus 로고
    • The mechanism of aminolysis of esters
    • Bunnett J.F., Davis G.T. The mechanism of aminolysis of esters. J. Am. Chem. Soc. 1960, 82:665-674.
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 665-674
    • Bunnett, J.F.1    Davis, G.T.2
  • 2
    • 0001058827 scopus 로고
    • General base catalysis of the aminolysis of phenyl acetate
    • Jencks W.P., Carriuolo J. General base catalysis of the aminolysis of phenyl acetate. J. Am. Chem. Soc. 1960, 82:675-681.
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 675-681
    • Jencks, W.P.1    Carriuolo, J.2
  • 3
    • 0000606860 scopus 로고
    • The influence of the leaving tendency of the phenoxy group on the ammonolysis and hydrolysis of substituted phenyl acetates
    • Bruice T.C., Mayahi M.F. The influence of the leaving tendency of the phenoxy group on the ammonolysis and hydrolysis of substituted phenyl acetates. J. Am. Chem. Soc. 1960, 82:3067-3071.
    • (1960) J. Am. Chem. Soc. , vol.82 , pp. 3067-3071
    • Bruice, T.C.1    Mayahi, M.F.2
  • 4
    • 0001361466 scopus 로고
    • The mechanism of the aminolysis of methyl formate
    • Blackburn G.M., Jencks W.P. The mechanism of the aminolysis of methyl formate. J. Am. Chem. Soc. 1968, 90:2638-2645.
    • (1968) J. Am. Chem. Soc. , vol.90 , pp. 2638-2645
    • Blackburn, G.M.1    Jencks, W.P.2
  • 5
    • 0001259182 scopus 로고
    • General base catalysis of the aminolysis of phenyl acetate by primary alkylamines
    • Jencks W.P., Gilchrist M. General base catalysis of the aminolysis of phenyl acetate by primary alkylamines. J. Am. Chem. Soc. 1966, 88:104-108.
    • (1966) J. Am. Chem. Soc. , vol.88 , pp. 104-108
    • Jencks, W.P.1    Gilchrist, M.2
  • 6
    • 0001466253 scopus 로고
    • Aminolysis of phenyl acetates in aqueous solutions. VII. Observations on the influence of salts, amine structure, and base strength
    • Bruice T.C., Donzel A., Huffman R.W., Butler A.R. Aminolysis of phenyl acetates in aqueous solutions. VII. Observations on the influence of salts, amine structure, and base strength. J. Am. Chem. Soc. 1967, 89:2106-2121.
    • (1967) J. Am. Chem. Soc. , vol.89 , pp. 2106-2121
    • Bruice, T.C.1    Donzel, A.2    Huffman, R.W.3    Butler, A.R.4
  • 7
    • 0000966541 scopus 로고
    • Isolation of a tetrahedral intermediate in an acetyl transfer reaction
    • Rogers G.A., Bruice T.C. Isolation of a tetrahedral intermediate in an acetyl transfer reaction. J. Am. Chem. Soc. 1973, 95:4452-4453.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 4452-4453
    • Rogers, G.A.1    Bruice, T.C.2
  • 8
    • 0016395451 scopus 로고
    • Synthesis and evaluation of a model for the so-called charge-relay system of the serine esterases
    • Rogers G.A., Bruice T.C. Synthesis and evaluation of a model for the so-called charge-relay system of the serine esterases. J. Am. Chem. Soc. 1974, 96:2473-2481.
    • (1974) J. Am. Chem. Soc. , vol.96 , pp. 2473-2481
    • Rogers, G.A.1    Bruice, T.C.2
  • 11
    • 0000379649 scopus 로고
    • Concerted mechanisms of acyl group transfer reactions in solution
    • Williams A. Concerted mechanisms of acyl group transfer reactions in solution. Acc. Chem. Res. 1989, 22:387-392.
    • (1989) Acc. Chem. Res. , vol.22 , pp. 387-392
    • Williams, A.1
  • 12
    • 49149109637 scopus 로고    scopus 로고
    • Predicting reactivities of organic molecules. Theoretical and experimental studies on the aminolysis of phenyl acetates
    • Galabov B., Ilieva S., Hadjieva B., Atanasov Y., Schaefer H.F. Predicting reactivities of organic molecules. Theoretical and experimental studies on the aminolysis of phenyl acetates. J. Phys. Chem. A 2008, 112:6700-6707.
    • (2008) J. Phys. Chem. A , vol.112 , pp. 6700-6707
    • Galabov, B.1    Ilieva, S.2    Hadjieva, B.3    Atanasov, Y.4    Schaefer, H.F.5
  • 13
    • 0001087039 scopus 로고    scopus 로고
    • Computational studies of the aminolysis of oxoesters and thioesters in aqueous solution
    • Yang W., Drueckhammer D.G. Computational studies of the aminolysis of oxoesters and thioesters in aqueous solution. Org. Lett. 2000, 2:4133-4136.
    • (2000) Org. Lett. , vol.2 , pp. 4133-4136
    • Yang, W.1    Drueckhammer, D.G.2
  • 14
    • 0001480124 scopus 로고
    • Quantum chemical studies of a model for peptide bond formation: formation of formamide and water from ammonia and formic acid
    • Oie T., Loew G.H., Burt S.K., Binkley J.S., McElroy R.D. Quantum chemical studies of a model for peptide bond formation: formation of formamide and water from ammonia and formic acid. J. Am. Chem. Soc. 1982, 104:6169-6174.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 6169-6174
    • Oie, T.1    Loew, G.H.2    Burt, S.K.3    Binkley, J.S.4    McElroy, R.D.5
  • 15
    • 0345457403 scopus 로고    scopus 로고
    • Bifunctional catalysis of ester aminolysis-a computational and experimental study
    • Wang L., Zipse H. Bifunctional catalysis of ester aminolysis-a computational and experimental study. Liebigs Ann. 1996, 1501-1509.
    • (1996) Liebigs Ann. , pp. 1501-1509
    • Wang, L.1    Zipse, H.2
  • 16
    • 33749094917 scopus 로고    scopus 로고
    • Polyether catalysis of ester aminolysis-a computational and experimental study
    • Zipse H., Wang L., Houk K.N. Polyether catalysis of ester aminolysis-a computational and experimental study. Liebigs Ann. 1996, 1511-1522.
    • (1996) Liebigs Ann. , pp. 1511-1522
    • Zipse, H.1    Wang, L.2    Houk, K.N.3
  • 18
    • 0034623527 scopus 로고    scopus 로고
    • Resolution of conflicting mechanistic observations in ester aminolysis. A warning on the qualitative prediction of isotope effects for reactive intermediates
    • Singleton D.A., Merrigan S.R. Resolution of conflicting mechanistic observations in ester aminolysis. A warning on the qualitative prediction of isotope effects for reactive intermediates. J. Am. Chem. Soc. 2000, 122:11035-11036.
    • (2000) J. Am. Chem. Soc. , vol.122 , pp. 11035-11036
    • Singleton, D.A.1    Merrigan, S.R.2
  • 19
    • 0037414493 scopus 로고    scopus 로고
    • Computational study of the aminolysis of 2-benzoxazolinone
    • Ilieva S., Galabov B., Musaev D.G., Morokuma K. Computational study of the aminolysis of 2-benzoxazolinone. J. Org. Chem. 2003, 68:3406-3412.
    • (2003) J. Org. Chem. , vol.68 , pp. 3406-3412
    • Ilieva, S.1    Galabov, B.2    Musaev, D.G.3    Morokuma, K.4
  • 20
    • 84961979209 scopus 로고    scopus 로고
    • DFT studies on the structure and stability of zwitterionic tetrahedral intermediate in the aminolysis of esters
    • Sung D.D., Koo I.S., Yang K., Lee I. DFT studies on the structure and stability of zwitterionic tetrahedral intermediate in the aminolysis of esters. Chem. Phys. Lett. 2006, 426:280-284.
    • (2006) Chem. Phys. Lett. , vol.426 , pp. 280-284
    • Sung, D.D.1    Koo, I.S.2    Yang, K.3    Lee, I.4
  • 21
    • 0032522186 scopus 로고    scopus 로고
    • What is the mechanism of catalysis of ester aminolysis by weak amine bases? Comparison of experimental studies and theoretical investigation of the aminolysis of substituted phenyl esters of quinoline-6- and -8-carboxylic acids
    • Adalstensson H., Bruice T.C. What is the mechanism of catalysis of ester aminolysis by weak amine bases? Comparison of experimental studies and theoretical investigation of the aminolysis of substituted phenyl esters of quinoline-6- and -8-carboxylic acids. J. Am. Chem. Soc. 1998, 120:3440-3447.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 3440-3447
    • Adalstensson, H.1    Bruice, T.C.2
  • 22
    • 0000200183 scopus 로고    scopus 로고
    • Ab initio study of the X-+RCOY displacement reactions with R=H, CH3 and X, Y=Cl, Br
    • Kim C.K., Li H.G., Lee H.W., Sohn C.K., Chun Y.I., Lee I. Ab initio study of the X-+RCOY displacement reactions with R=H, CH3 and X, Y=Cl, Br. J. Phys. Chem. A 2000, 104:4069-4076.
    • (2000) J. Phys. Chem. A , vol.104 , pp. 4069-4076
    • Kim, C.K.1    Li, H.G.2    Lee, H.W.3    Sohn, C.K.4    Chun, Y.I.5    Lee, I.6
  • 23
    • 0001615022 scopus 로고    scopus 로고
    • Can transacylation reactions occur via S(N)2 pathways in the gas phase? Insights via ion-molecule reactions of N-acylpyridinium ions and ab initio calculations
    • O'Hair R.A.J., Androutsopoulos N.K. Can transacylation reactions occur via S(N)2 pathways in the gas phase? Insights via ion-molecule reactions of N-acylpyridinium ions and ab initio calculations. Org. Lett. 2000, 2:2567-2570.
    • (2000) Org. Lett. , vol.2 , pp. 2567-2570
    • O'Hair, R.A.J.1    Androutsopoulos, N.K.2
  • 24
    • 0035961095 scopus 로고    scopus 로고
    • Computer simulation of amide bond formation in aqueous solution
    • Chalmet S., Harb W., Ruiz-López M.F. Computer simulation of amide bond formation in aqueous solution. J. Phys. Chem. A 2001, 105:11574-11581.
    • (2001) J. Phys. Chem. A , vol.105 , pp. 11574-11581
    • Chalmet, S.1    Harb, W.2    Ruiz-López, M.F.3
  • 25
    • 84962374950 scopus 로고    scopus 로고
    • Computational study of the aminolysis of esters. The reaction of methylformate with ammonia
    • Ilieva S., Galabov B., Musaev D.G., Morokuma K., Schaefer H.F. Computational study of the aminolysis of esters. The reaction of methylformate with ammonia. J. Org. Chem. 2003, 68:1496-1502.
    • (2003) J. Org. Chem. , vol.68 , pp. 1496-1502
    • Ilieva, S.1    Galabov, B.2    Musaev, D.G.3    Morokuma, K.4    Schaefer, H.F.5
  • 26
    • 33750483620 scopus 로고    scopus 로고
    • Theoretical studies on the aminolysis of phenyl formate. Mechanism and solvent effect
    • Jin L., Wu Y., Xue Y., Guo Y., Xie D.Q., Yan G.S. Theoretical studies on the aminolysis of phenyl formate. Mechanism and solvent effect. Acta Chim. Sin. 2006, 64:873-878.
    • (2006) Acta Chim. Sin. , vol.64 , pp. 873-878
    • Jin, L.1    Wu, Y.2    Xue, Y.3    Guo, Y.4    Xie, D.Q.5    Yan, G.S.6
  • 27
    • 40849130834 scopus 로고    scopus 로고
    • The substituent effects of the leaving groups on the aminolysis of phenyl acetates: DFT studies
    • Yi G.Q., Zeng Y., Xia X.F., Xue Y., Kim C.K., Yan G.S. The substituent effects of the leaving groups on the aminolysis of phenyl acetates: DFT studies. Chem. Phys. 2008, 345:73-81.
    • (2008) Chem. Phys. , vol.345 , pp. 73-81
    • Yi, G.Q.1    Zeng, Y.2    Xia, X.F.3    Xue, Y.4    Kim, C.K.5    Yan, G.S.6
  • 28
    • 84961983451 scopus 로고    scopus 로고
    • Mechanism of the aminolysis of methyl benzoate: a computational study
    • Galabov B., Atanasov Y., Ilieva S., Schaefer H.F. Mechanism of the aminolysis of methyl benzoate: a computational study. J. Phys. Chem. A 2005, 109:11470-11474.
    • (2005) J. Phys. Chem. A , vol.109 , pp. 11470-11474
    • Galabov, B.1    Atanasov, Y.2    Ilieva, S.3    Schaefer, H.F.4
  • 30
    • 0004465903 scopus 로고
    • A formulation of the reaction coordinate
    • Fukui K. A formulation of the reaction coordinate. J. Phys. Chem. 1970, 74:4161-4163.
    • (1970) J. Phys. Chem. , vol.74 , pp. 4161-4163
    • Fukui, K.1
  • 31
    • 0011083499 scopus 로고
    • Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint
    • Reed A.E., Curtiss L.A., Weinhold F. Intermolecular interactions from a natural bond orbital, donor-acceptor viewpoint. Chem. Rev. 1988, 88:899-926.
    • (1988) Chem. Rev. , vol.88 , pp. 899-926
    • Reed, A.E.1    Curtiss, L.A.2    Weinhold, F.3
  • 32
    • 84961985847 scopus 로고    scopus 로고
    • Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model
    • Barone V., Cossi M. Quantum calculation of molecular energies and energy gradients in solution by a conductor solvent model. J. Phys. Chem. A 1998, 102:1995-2001.
    • (1998) J. Phys. Chem. A , vol.102 , pp. 1995-2001
    • Barone, V.1    Cossi, M.2
  • 34
    • 33947440291 scopus 로고
    • Atomic radii and interatomic distances in metals
    • Pauling L. Atomic radii and interatomic distances in metals. J. Am. Chem. Soc. 1947, 69:542-553.
    • (1947) J. Am. Chem. Soc. , vol.69 , pp. 542-553
    • Pauling, L.1
  • 35
    • 0001633471 scopus 로고
    • A theoretical study on the mechanism of the thermal and the acid-catalyzed decarboxylation of 2-oxetanones (-lactones)
    • Moyano A., Pericàs M.A., Valentí A. A theoretical study on the mechanism of the thermal and the acid-catalyzed decarboxylation of 2-oxetanones (-lactones). J. Org. Chem. 1989, 54:573-582.
    • (1989) J. Org. Chem. , vol.54 , pp. 573-582
    • Moyano, A.1    Pericàs, M.A.2    Valentí, A.3
  • 36
    • 0010884753 scopus 로고
    • On the energy of oxidation-reduction reactions involving electron transfer
    • Marcus R.A. On the energy of oxidation-reduction reactions involving electron transfer. J. Chem. Phys. 1956, 24:966-978.
    • (1956) J. Chem. Phys. , vol.24 , pp. 966-978
    • Marcus, R.A.1
  • 37
    • 0030889154 scopus 로고    scopus 로고
    • Theory of substituent effects on pericyclic reaction rates: alkoxy substituents in the claisen rearrangement
    • Yoo H.Y., Houk K.N. Theory of substituent effects on pericyclic reaction rates: alkoxy substituents in the claisen rearrangement. J. Am. Chem. Soc. 1997, 119:2877-2884.
    • (1997) J. Am. Chem. Soc. , vol.119 , pp. 2877-2884
    • Yoo, H.Y.1    Houk, K.N.2
  • 38
    • 0021094581 scopus 로고
    • Relationship between More O'Ferrall plots and Marcus rate theory. Overriding orbital-symmetry constraints on chemical reactions
    • Murdoch J.R. Relationship between More O'Ferrall plots and Marcus rate theory. Overriding orbital-symmetry constraints on chemical reactions. J. Am. Chem. Soc. 1983, 105:2660-2667.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 2660-2667
    • Murdoch, J.R.1
  • 39
    • 0005858208 scopus 로고
    • A simple relationship between empirical theories for predicting barrier heights of electron-, proton-, atom-, and group-transfer reactions
    • Murdoch J.R. A simple relationship between empirical theories for predicting barrier heights of electron-, proton-, atom-, and group-transfer reactions. J. Am. Chem. Soc. 1983, 105:2159-2164.
    • (1983) J. Am. Chem. Soc. , vol.105 , pp. 2159-2164
    • Murdoch, J.R.1


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