Abstract
A theoretical study of the effect of substitution on the 1,3-dipolar cycloaddition of benzonitrile oxide was performed using the DFT method at the B3LYP level of theory using 6–311G(d,p) basis sets. Equilibrium molecular geometries and harmonic vibrational frequencies of the reactants, transition state, and product were calculated. The corresponding rate constants and activation parameters were calculated. The results showed good agreement with experimental data. These calculations indicated that the reaction proceeds through an asynchronous mechanism.
References
1.
Huisgen R.
(1984 ) 1,3-Dipolar cycloadditions chemistry. Wiley , New York .
2.
Huisgen R.
(1963 ) Angew. Chem. int. Ed. Eng. , 2 , 565 .
3.
Firestone R.A.
(1968 ) J. Org. Chem. , 33 , 2285 .
4.
Huisgen R.
(1968 ) J. Org. Chem. , 33 , 2291 .
5.
Huisgen R.
(1976 ) J. Org. Chem. , 41 , 403 .
6.
Huisgen R.
,
Fisera L.
,
Giera H.
, and
Sustmann R.
(1995 ) J. Am. Chem. Soc. , 117 , 9671 .
7.
Zardoost M.R.
,
Siadati S.A.
, and
Boodaghi A.
(2010 ) Iran. J. Org. Chem. , 2 , 377 .
8.
Zardoost M.R.
,
Siadati S.A.
, and
Toosse M.R.
(2010 ) J. Phys. Theor. Chem. , 7 , 155 .
9.
Zardoost M.R.
, and
Siadati S.A.
(2012 ) Prog. Reac. Kinet. Mech. , 37 , 436 .
10.
Ito K.
, and
Saito K.
(1995 ) Bull. Chem. Soc. Jpn. , 68 , 3539 .
11.
Irani M.
,
Haqgu M.
,
Talebi A.
, and
Gholami M.R.
(2009 ) J. Mol. Struc. THEOCHEM. , 893 , 73 .
12.
Kamiya K.
,
Matsui T.
,
Sugimura T.
, and
Shigeta Y.
(2012 ) J. Phys. Chem. A , 116 , 1168 .
13.
Koyama M.
,
Tsuboi H.
,
Endou A.
,
Takaba H.
,
Kubo M.
,
Del Carpio C.A.
, and
Miyamoto A.
(2007 ) Comb. Chem. high throughput screen. , 10 , 99 .
14.
Zardoost M.R.
,
Siadati S.A.
(2013 ) Comb. Chem. high throughput screen. , 16 , 408 .
15.
Frisch M.J.
,
Trucks G.W.
,
Schlegel H.B.
Gaussian, Inc. , Pittsburgh PA , 2003 .
16.
Becke A.D.
(1988 ) Phys. Rev. A. , 38 , 3098 .
17.
Lee C.
,
Yang W.
, and
Parr R.G.
(1988 ) Phys. Rev. B. , 371 , 785 .
18.
Krishnan R.
,
Binkley J.S.
,
Seeger R.
, and
Pople J.A.
(1980 ) J. Chem. Phys. , 72 , 650 .
19.
Peng C.
,
Ayala P.Y.
,
Schlegel H.B.
, and
Frisch M.J.
(1996 ) J. Comp. Chem. , 17 , 49 .
20.
Gonzalez C.
, and
Schlegel H.B.
(1990 ) J. Phys. Chem. , 94 , 5523 .
21.
Gonzalez C.
, and
Schlegel H.B.
(1989 ) J. Chem. Phys. , 90 , 2154 .
22.
Reed A.E.
,
Curtiss L.A.
, and
Weinhold F.
(1988 ) Chem. Rev. , 88 , 899 .
23.
Carpenter J.E.
, and
Weinhold F.
(1988 ) J. Mol. Struct.: THEOCHEM. , 169 , 41 .
24.
Barone V.
, and
Cossi M.
(1998 ) J. Phys. Chem. A , 102 , 1995 .
25.
Glasstone S.
,
Laidler K.J.
, and
Eyring H.
(1941 ) The theory of rate processes. McGraw-Hill , New York .
26.
Laidler K.J.
(1969 ) Theories of chemical reaction rates. McGraw-Hill , New York .
27.
Pauling L.
(1947 ) J. Am. Chem. Soc. , 9 , 542 .