The second-order rate constants for the nucleophilic substitution reactions of para-substituted benzyl nitrates with para-substituted anilines in acetonitrile were conductometrically determined. Hammett ${\rho}$x and ${\rho}$y values and Bronsted ${\beta}$ values were obtained from these kinetic data. The reactions of Benzyl nitrates with the series of anilines showed linear Hammett plots with negative slopes. For the change of substituents in the benzyl nitrates, nonlinear Hammett plots with a concave upwards curve were obtained. We applied the potential energy surface and the quantum mechanical models in order to examine the transition state variations caused by changes in substituents on the nucleophile and the substrate. The results showed that the reaction was proceeded via the $S_{N}2$-type reaction mechanism in which the extent of bond-formation was greatly changed depending on the property of the substituents in substrate.
Citing 'The Nucleophilic Substitution Reactions of the Nitrate Group. The Kinetics of Substituted Benzyl Nitrates with Anilines in Acetonitrile
'
@article{ JCGMDC_1989_v33n1_31}
,title={The Nucleophilic Substitution Reactions of the Nitrate Group. The Kinetics of Substituted Benzyl Nitrates with Anilines in Acetonitrile}
,volume={1}
, number= {1}
, journal={Journal of the Korean Chemical Society}
, publisher={Korean Chemical Society}
, author={Wang Ki, Kim
and
Chang Kook, Sohn}
, year={1989}
, month={Feb}
TY - JOUR
T2 - Journal of the Korean Chemical Society
AU - Wang Ki, Kim
AU - Chang Kook, Sohn
SN - 1017-2548
TI - The Nucleophilic Substitution Reactions of the Nitrate Group. The Kinetics of Substituted Benzyl Nitrates with Anilines in Acetonitrile
VL - 33
PB - Korean Chemical Society
PY - 1989
ER -
Wang Ki, K.
,
&
Chang Kook, S.
( 1989).
The Nucleophilic Substitution Reactions of the Nitrate Group. The Kinetics of Substituted Benzyl Nitrates with Anilines in Acetonitrile.
Journal of the Korean Chemical Society,
33
(1)
Korean Chemical Society.
Wang Ki, K
,
&
Chang Kook, S
1989,
The Nucleophilic Substitution Reactions of the Nitrate Group. The Kinetics of Substituted Benzyl Nitrates with Anilines in Acetonitrile,
Journal of the Korean Chemical Society,
vol. 1,
no. 1,
[1]
K Wang Ki
,
and
S Chang Kook
,
“The Nucleophilic Substitution Reactions of the Nitrate Group. The Kinetics of Substituted Benzyl Nitrates with Anilines in Acetonitrile”,
Journal of the Korean Chemical Society,
vol. 1,
no. 1,
Feb
1989.
Wang Ki, Kim
and
,
Chang Kook, Sohn
and
,
“The Nucleophilic Substitution Reactions of the Nitrate Group. The Kinetics of Substituted Benzyl Nitrates with Anilines in Acetonitrile”
Journal of the Korean Chemical Society,
1.
1
1989:
Wang Ki, K
,
Chang Kook, S
The Nucleophilic Substitution Reactions of the Nitrate Group. The Kinetics of Substituted Benzyl Nitrates with Anilines in Acetonitrile.
Journal of the Korean Chemical Society
[Internet].
1989.
Feb ;
1
(1)
Wang Ki, Kim
,
and
Chang Kook, Sohn
,
“The Nucleophilic Substitution Reactions of the Nitrate Group. The Kinetics of Substituted Benzyl Nitrates with Anilines in Acetonitrile.”
Journal of the Korean Chemical Society
1
no.1
()
Feb,
1989):
