Abstract
A theoretical study on the regioselectivity of 1,3-dipolar cycloaddition reactions between methyleneamine N-oxide (nitrone) and cyclopent-3-Ene-1,2-Dione (DPhl), pyrrole-2,3-dione (DPh2), furan-2,3-dione (DPh3) and thiophene-2,3- dione (DPh4) has been carried out by means of several theoretical approaches, namely, activation energies, Houk's rule based on FMO theory and DFT reactivity indices. The calculations were performed at the DFT-B3LYP/6-31G(d) level of theory using Gaussian 03. The present analysis shows that these reactions have an NED character. Moreover, the results obtained from energetic and electronic approaches, with the exception of Gazquez - Mendez rule based on NPA analysis, confirm that 1,5-regioisomer is the major product.
Keywords
References
1.
Lakhvich F.A.
,
Koroleva E.V.
, and
Akhrem A.A.
(1989 ) Chem. Heterocyclic Compd. , 25 , 359 –375 .
2.
Agirbas H.
,
Guner S.
,
Budak F.
,
Keceli S.
,
Kandemirli E
,
Shvets N.
,
Kovalishyn Y
, and
Dimoglo A.
(2007 ) Bioorg. Med. Chem. , 15 , 2322 –2333 .
3.
Kumar Das T.
,
Salampuria S.
, and
Banerjee M.
(2010 ) J. Mol. Struct. (THEOCHEM) , 959 , 22 –29 .
4.
Benchouk W.
, and
Mekelleche S.M.
(2008 ) J. Mol. Struct. (THEOCHEM) , 852 , 46 –53 .
5.
Merino R
,
Tejero T
,
Chiacchio U.
,
Romeo G.
, and
Rescifina A.
(2007 ) Tetrahedron , 63 , 1448 –1458 .
6.
Merino R
,
Revuelta J.
,
Tejero T
,
Chiacchio U.
,
Rescifina A.
, and
Romeo G.
(2003 ) Tetrahedron , 63 , 3581 –3592 .
7.
Moeinpour E
(2010 ) Chin. J. Chem. Phys. , 23 , 165 –168 .
8.
Stinson S.C.
(1998 ) Chem. Eng. News , 76 , 83 –104 .
9.
Huisgen R.
,
Grashey R.
, and
Sauer J.
(1964 ) Chemistry of alheñes. Interscience , New York .
10.
Pérez R
,
Domingo L.R.
,
Aurell M.J.
, and
Contreras R.
(2003 ) Tetrahedron , 59 , 3117 –3125 .
11.
Huisgen R.
(1984 ) 1,3-Dipolar cycloadditions chemistry. Wiley , New York .
12.
Huisgen R.
(1968 ) J. Org. Chem. , 33 , 2291 –2297 .
13.
Huisgen R.
(1976 ) J. Org. Chem. , 41 , 403 –419 .
14.
Carey EA
., and
Sundberg R.J.
(2007 ) Advanced organic chemistry , 5th edn. Springer , New York .
15.
Benchouk W.
, and
Mekelleche S.M.
(2008 ) J. Mol. Struct. (THEOCHEM) , 862 , 1 –6 .
16.
Fleming I.
(1976 ) Frontier orbitals and organic chemical reactions. Wiley , London .
17.
Sustmann R.
, and
Shubert R.
(1972 ) Tetrahedron Lett. , 13 , 2739 –2742 .
18.
Sustmann R.
, and
Trill H.
(1972 ) Tetrahedron Lett. , 13 , 4271 –4274 .
19.
Sustmann R.
(1974 ) Pure Appl. Chem. , 40 , 569 –593 .
20.
Domingo L.R.
,
Aurell M.J.
,
Amó M.A.
, and
Sász J.A.
(2007 ) J. Mol. Struct. (THEOCHEM) , 811 , 125 –133 .
21.
Chandra A.K.
, and
Nguyen M.T.
(1998 ) J. Phys. Chem., A , 102 , 6181 –6185 .
22.
Sharma R
,
Kumar A.
, and
Sahu V.
(2010 ) J. Phys. Chem., A , 114 , 1032 –1038 .
23.
Parthasarathi R.
, and
Chattaraj P.K.
(2004 ) Bioorg. Med. Chem. , 12 , 5533 –5543 .
24.
Chattaraj P.K.
, and
Sarkar U.
(2006 ) Chem. Rev. , 106 , 2065 –2091 .
25.
Yang W.
, and
Mortier W.J.
(1986 ) J. Am. Chem. Soc. , 108 , 5708 –5711 .
26.
Padmanabhan J.
,
Parthasarathi R.
, and
Chattaraj P.K.
(2006 ) Chem. Res. Toxicol. , 19 , 356 –364 .
27.
Nacereddine A.K.
,
Yahia W
,
Bouacha S.
, and
Djerourou A.
(2010 ) Tetrahedron Lett. , 51 , 2617 –2621 .
28.
Domingo L.R.
,
Aurell M.J.
,
Jalal R.
, and
Esseffar M.
(2010 ) J. Mol. Struct. (THEOCHEM) , 942 , 26 –31 .
29.
Houk K.N.
(1975 ) Acc. Chem. Res. , 8 , 361 –369 .
30.
Kohn W.
,
Becke A.D.
, and
Parr R.G.
(1996 ) J. Phys. Chem. , 100 , 12974 –12980 .
31.
Chattaraj P.K.
,
Sarker U.
, and
Ranjan Roy D.
(2006 ) Chem. Rev. , 106 , 2065 –2091 .
32.
Koopmans T.A.
(1934 ) Phys ica , 1 , 104 –113 .
33.
Parr R.G.
,
von Szentpaly L.
, and
Liu S.
(1999 ) J. Am. Chem. Soc. , 121 , 1922 –1924 .
34.
Ghomri A.
, and
Mekelleche S.M.
(2010 ) J. Mol. Struct. (THEOCHEM) , 941 , 36 –40 .
35.
Xia Y
,
Yin D.
,
Rong C.
,
Xu Q.
,
Yin D.
, and
Liu S.
(2008 ) J. Phys. Chem. , 112 , 9970 –9977 .
36.
Chandra A.K.
, and
Nguyen M.T.
(2002 ) Int. J. Mol. Sci. , 3 , 310 –323 .
37.
Chandra A.K.
, and
Nguyen M.T.
(1998 ) J. Phys. Chem. A , 102 , 6181 –6185 .
38.
Yang W.
, and
Mortier W.J.
(1986 ) J. Am. Chem. Soc. , 108 , 5708 –5711 .
39.
Chemouri H.
, and
Mekelleche S.M.
(2007 ) J. Mol. Struct. (THEOCHEM) , 813 , 67 –72 .
40.
Aurell M.J.
,
Domingo L.R.
,
Pérez P.
, and
Contreras R.
(2004 ) Tetrahedron , 60 , 11503 –11509 .
41.
Frisch Æ.
,
Frisch M.J.
, and
Trucks G.W.
Gaussian 03 User's Reference. Gaussian, Inc Carnegie Office Park , Bldg. 6, Carnegie, PA 15106 USA.
42.
Gordon M.H.
, and
Pople J.A.
(1988 ) J. Chem. Phys. , 89 , 5777 –5786 .
43.
González C.
, and
Schlegel H.B.
(1990 ) J. Phys. Chem. , 94 , 5523 –5527 .
44.
González C.
, and
Schlegel H.B.
(1991 ) J. Chem. Phys. , 95 , 5853 –5860 .
45.
Reed A.E.
, and
Weinhold F.
(1983 ) J Chem. Phys. , 78 , 4066 –4073 .
46.
Frisch M.J.
,
Trucks G.W.
,
Schlegel H.B.
2004 ) Gaussian 03, Revision E.01 , Gaussian, Inc. , Wallingford CT.
47.
Gazquez J.L.
, and
Mendez F.
(1994 ) J. Phys. Chem. , 98 , 4591 –4593 .
48.
Chandra A.K.
, and
Nguyen M.T.
(2002 ) Int. J. Mol. Sci. , 3 , 310 –323 .