The geometric structures of the phenoxenium cation which is a cation intermediate of 2-azaspiro ring compounds (2-azaspiro[4.5]decane) from N-methoxy-N-prenylbenzamide are studied by means of the Hamiltonian algorithm with ab intio molecular orbital calculations at HF/3-21G level. The geometries are further refined with MP2/6-311G** level. We tried four substituted compounds with the methyl group. Among them only one compound with two methyl groups gives a ring-closure intermediate, which agrees well with the experimental results.

1.
H.
Deguchi
,
Y.
Kubota
,
Y.
Yagi
,
I.
Mitani
,
Y.
Imai
,
M.
Tatsumi
,
N.
Watari
,
Y.
Kameda
,
Ind. Eng. Chem. Res.
,
49
,
6
13
(
2010
).
2.
J-G
Shim
,
J-H
Kim
,
Y. H.
Jhon
,
J.
Kim
,
K-H
Cho
,
Ind. Eng. Chem. Res.
,
48
,
2172
2178
(
2009
).
3.
Gaussian 09, Revision A.02
,
M. J.
Frisch
, et al 
2009
,
Gaussian, Inc.
,
Wallingford CT
.
4.
H.
Teramae
,
T.
Ishimoto
,
U.
Nagashima
.,
Theor. Chem. Acc.
,
130
,
671
678
(
2011
)
5.
M. W.
Schmidt
,
K. K.
Baldridge
,
J. A.
Boatz
,
S. T.
Elbert
,
M. S.
Gordon
,
J. H.
Jensen
,
S.
Koseki
,
N.
Matsunaga
,
K. A.
Nguyen
,
S.
Su
,
T. L.
Windus
,
M.
Dupuis
,
J. A.
Montgomery
, Jr.
,
J. Comput. Chem.
,
14
,
1347
1363
(
1993
).
6.
K.
Ohtawara
,
H.
Teramae
,
Chem. Phys. Lett.
390
,
84
(
2004
).
7.
T.
Ishimoto
,
H.
Tokiwa
,
H.
Teramae
,
U.
Nagashima
,
Chem. Phys. Lett.
,
387
,
460
(
2004
)
8.
T.
Ishimoto
,
H.
Tokiwa
,
H.
Teramae
,
U.
Nagashima
J. Chem. Phys.
,
122
,
094905
(
2005
)
9.
H.
Teramae
,
K.
Ohtawara
,
T.
Ishimoto
,
U.
Nagashima
,
Bull. Chem. Soc. Jpn.
,
81
,
1094
(
2008
)
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