2.7 Chemical Reactions
79
HOMO
(a)
(b)
NO 2
+
H
+
NO 2
1
2
1
2
Fig. 2.70 a Electrophilic substitution reaction between naphthalene and NO 2
+ . b The HOMO
pattern of naphthalene showing favorable site (indicated by red arrow) in electrophilic reaction
based on the calculation by the HF/3-21G method
HCl (X = Cl)
LUMO
1-Butene (R = C 2 H 5 )
HOMO
R
H
H
H
HX
R
H
H
H
X
H
1
2
1
2
LL
SS
(a)
(b)
Fig. 2.71 a Chemical reaction between non-symmetric olefin RCH=CH 2 and hydrogen halide HX
showing Markovnikov’s rule and (b) HOMO-LUMO interaction between the end-carbon (C 1 ) of
1-butene and the proton of HCl (X = Cl) (see text) based on the calculation by the HF/3-21G method
79
HOMO
(a)
(b)
NO 2
+
H
+
NO 2
1
2
1
2
Fig. 2.70 a Electrophilic substitution reaction between naphthalene and NO 2
+ . b The HOMO
pattern of naphthalene showing favorable site (indicated by red arrow) in electrophilic reaction
based on the calculation by the HF/3-21G method
HCl (X = Cl)
LUMO
1-Butene (R = C 2 H 5 )
HOMO
R
H
H
H
HX
R
H
H
H
X
H
1
2
1
2
LL
SS
(a)
(b)
Fig. 2.71 a Chemical reaction between non-symmetric olefin RCH=CH 2 and hydrogen halide HX
showing Markovnikov’s rule and (b) HOMO-LUMO interaction between the end-carbon (C 1 ) of
1-butene and the proton of HCl (X = Cl) (see text) based on the calculation by the HF/3-21G method