Abstract
A comprehensive theoretical study was performed regarding the solvent effect on the Diels–Alder reaction of 2,3-dimethyl-1,3-butadiene and the hetero-dienophile, diethyl azodicarboxylate. Reaction rates in the various solutions were studied using SCRF–DFT theory and good agreement with the experimental results was obtained. According to natural bond orbital analysis, it was confirmed that the stabilisation energy of the C–N bonds contributes to the strong interaction between the solvents and transition state (TS) structures. Topological analyses showed a linear correlation between the interaction energy and the sum of electron density at the bond critical point of C–N at the TS. Moreover, with an increase in the overall electron density of the C–N bond critical point, the vibrational frequencies were decreased. Finally, some correlations between the quantum reactivity indices and the rate constants in the presence of 23 solvents were investigated.
Keywords
References
1.
Katritzky A.R.
,
Fara D.C.
,
Yang H.
, and
Tämm K.
(2004 ) Chem. Rev. , 104 , 175 –198 .
2.
Sahin H.T.
, and
Arslan M.B.
(2008 ) Int. J. Mol. Sci. , 9 , 78 –88 .
3.
Setiyanto H.
,
Saraswaty V.
,
Hertadi R.
,
Noviandri I.
, and
Buchari B.
(2011 ) Int. J. Electrochem. Sci. , 6 , 2090 –2100 .
4.
Maki B.E.
,
Patterson E.V.
,
Cramer C.J.
, and
Scheidt K.A.
(2009 ) Org. Lett. , 48 , 3942 –3945 .
5.
Iglesias E.
(2005 ) New J. Chem. , 29 , 625 –632 .
6.
Ghosh K.K.
, and
Patle S.K.
(2002 ) Indian J. Chem., Sect. A: Inorg., Bio-inorg., Phys., Theor. Anal. Chem. , 41 , 758 –762 .
7.
Gericke M.
,
Fardim P.
, and
Heinze T.
(2012 ) Molecules , 17 , 7458 –7502 .
8.
Reichardt C.
,
Asharin-Fard S.
,
Blum A.
,
Eschner M.
,
Mehranpour A.-M.
,
Milart P.
,
Niem T.
,
Schafer G.
, and
Wilk M.
(1993 ) Pure Appl. Chem. , 65 , 2593 –2601 .
9.
Puigmartí-Luis J.
,
Pérez del Pino Á.
,
Laukhin V.
,
Feldborg L.N.
,
Rovira C.
,
Laukhina E.
, and
Amabilino D.B.
(2010 ) J. Mater. Chem. , 20 , 466 –474 .
10.
Dalpozzo R.
,
Bartoli G.
, and
Bencivenni G.
(2011 ) Symmetry , 3 , 84 –125 .
11.
Desimoni G.
,
Faita G.
,
Righetti P.P.
, and
Toma L.
(1990 ) Tetrahedron , 46 , 7951 –7970 .
12.
Desimoni G.
,
Faita G.
,
Pasini D.
, and
Righetti P.P.
(1992 ) Tetrahedron , 48 , 1667 –1674 .
13.
Desimoni G.
,
Faita G.
,
Righetti P.P.
,
Sfulcini A.
, and
Tsyganov D.
(1994 ) Tetrahedron , 50 , 1821 –1832 .
14.
Reichardt C.
(2004 ) Solvents and solvent effects in organic chemistry , pp. 155 –195 . Wiley-VCH , Weinheim, Germany .
15.
Osuna S.
,
Kim S.
,
Bollot G.
, and
Houk K.N.
(2013 ) Eur. J. Org. Chem. , 14 , 2823 –2831 .
16.
Nowicki J.
(2000 ) Molecules , 5 , 1033 –1050 .
17.
Berne B.J.
,
Borkovec M.
, and
Straub J.E.
(1988 ) J. Phys. Chem. , 92 , 3711 –3725 .
18.
Truhlar D.G.
,
Garrett B.C.
, and
Klippenstein S.J.
(1996 ) J. Phys. Chem. , 100 , 12771 –12800 .
19.
Ainavarapu S.R.K.
,
Wiita A.P.
,
Dougan L.
,
Uggerud E.
, and
Fernandez J.M.
(2008 ) J. Am. Chem. Soc. , 130 , 6479 –6487 .
20.
Soto-Delgado J.
,
Aizman A.
,
Contreras R.
, and
Domingo L.R.
(2012 ) Molecules , 17 , 13687 –13703 .
21.
Nandi S.
,
Monesil A.
,
Drgan V.
,
Merzel F.
, and
Novič M.
(2013 ) Chem. Cent. J. , 7 , 171 –183 .
22.
Náray-Szabó G.
,
Oláh B.
, and
Krámos J.
(2013 ) Biomolecules , 3 , 662 –702 .
23.
Duan Y.
,
Wu C.
,
Chowdhury S.
,
Lee M.C.
,
Xiong G.
,
Zhang W.
,
Yang R.
,
Cieplak P.
,
Luo R.
,
Lee T.
,
Caldwell J.
,
Wang J.
, and
Kollman P.
(2003 ) J. Comput. Chem. , 24 , 1999 –2012 .
24.
Gao J.
, and
Truhlar D.G.
(2002 ) Annu. Rev. Phys. Chem. , 53 , 467 –505 .
25.
Glover W.J.
,
Larsen R.E.
, and
Schwartz B.J.
(2010 ) J. Phys. Chem. Lett. , 1 , 165 –169 .
26.
Ángyán J.G.
(1992 ) J. Math. Chem. , 10 , 93 –137 .
27.
Lewars E.
(1983 ) Chem. Rev. , 83 , 519 –534 .
28.
Greathouse J.A.
,
Johnson K.L.
, and
Greenwell H.C.
(2014 ) Minerals , 4 , 519 –540 .
29.
Hohenberg P.
, and
Kohn W.
(1964 ) Phys. Rev. [Sect.] B , 136 , 864 –871 .
30.
Frisch M.J.
,
Trucks G.W.
,
Schlegel H.B.
2009 ) Gaussian 09, revision A.1. Gaussian, Inc. , Wallingford, CT .
31.
Lee C.
,
Yang W.
, and
Parr R.G.
(1988 ) Phys. Rev. B: Condens. Matter Mater. Phys. , 37 , 785 –789 .
32.
Sharifi Y.
, and
Achenie L.E.K.
(2014 ) J. Chem. Proc. Eng. , 1 , 104 –109 .
33.
Anouar E.H.
,
Shah S.A.A.
,
Hassan N.B.
,
Moussaoui N.E.
,
Ahmad R.
,
Zulkefeli M.
, and
Weber J.-F.F.
(2014 ) Molecules , 19 , 3489 –3507 .
34.
Eckart C.
(1930 ) Phys. Rev. , 35 , 1303 –1309 .
35.
Reed A.E.
,
Curtiss L.A.
, and
Weinhold F.
(1988 ) Chem. Rev. , 88 , 899 –926 .
36.
Weinhold F.
, and
Landis C.R.
(2001 ) Chem. Educ. Res. Pract. Eur. , 2 , 91 –104 .
37.
Bader R.F.W.
(1962 ) Can. J. Chem. , 40 , 1164 –1175 .
38.
Bader R.F.W.
, and
Jones G.A.
(1963 ) Can. J. Chem. , 41 , 586 –606 .
39.
Bader R.F.W.
, and
Jones G.A.
(1963 ) J. Chem. Phys. , 38 , 2791 –2802 .
40.
Bader R.F.W.
(1964 ) J. Am. Chem. Soc. , 86 , 5070 –5075 .
41.
Bader R.F.W.
,
Henneker W.H.
, and
Cade P.E.
(1967 ) J. Chem. Phys. , 46 , 3341 –3363 .
42.
Desimoni G.
,
Faita G.
,
Righetti P.P.
, and
Toma L.
(1990 ) Tetrahedron , 46 , 7951 –7970 .
43.
Kawashima Y.
,
Nakano H.
,
Jung J.
, and
Ten-no S.
(2011 ) Phys. Chem. Chem. Phys. , 13 , 11731 –11738 .
44.
Geerlings P.
, and
De Prof F.
(2002 ) Int. J. Mol. Sci. , 3 , 276 –309 .
45.
Wijnen J.W.
, and
Engberts J.B.F.N.
(1997 ) J. Org. Chem. , 62 , 2039 –2044 .
46.
Bach R.D.
,
McDouall J.J.W.
, and
Schlegel H.B.
(1989 ) J. Org. Chem. , 54 , 2931 –2935 .
47.
Guner V.
,
Khuong K.S.
,
Leach A.G.
,
Lee P.S.
,
Bartberger M.D.
, and
Houk K.N.
(2003 ) J. Phys. Chem. A , 107 , 11445 –11459 .
48.
Bader R.F.W.
(1991 ) Chem. Rev. , 91 , 893 –925 .
49.
Abbasoglu R.
,
Atalay A.
, and
Şenocak A.
(2014 ) Indian J. Chem., Sect. A: Inorg., Bio-inorg., Phys., Theor. Anal. Chem. , 53 , 288 –293 .
50.
Tia R.
,
Asempa E.
, and
Adei E.
(2014 ) J. Theor. Comput. Sci. , 1 , 1 –12 .
51.
Udhayakalaa P.
,
Maxwell Samuelb A.
,
Rajendiranc T.V.
, and
Gunasekarand S.
(2013 ) Scholars Research Library , 5 , 272 –283 .
52.
Liu S.
(2005 ) J. Chem. Sci. , 117 , 477 –483 .
53.
Koopmans T.
(1934 ) Physica , 1 , 104 –113 .
54.
Kohn W.
, and
Sham L.
(1985 ) Phys. Rev. [Sect.] A, 140 , 1133 –1138 .