Abstract
The reaction between phenacyl bromide and 2-mercaptobenzothiazole was studied conductometrically in 17 different protic and aprotic solvents. The second order rate constants determined are found to be highly susceptible to changes in the solvation abilities of the solvents. Correlation of the rate constants with different solvent parameters indicated that the solvation of the reactants and the transition state is due to the electrophilicity, hydrogen bond donor ability, specific polarisability and a non-specific polarity of the solvent. by statistical analysis, a linear solvation energy relationship is derived and the percentage contributions of each type of solvation are estimated.
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References
1.
Koppel I.A.
, and
Palm VA
. (1972 ) In:
Chapman N.V.
, and
Shorter J.
(eds.). Advances in linear free energy relationship , p. 222 . Plenum Press , New York .
2.
Reichardt C.
(1979 ) Ang. Chem. , 18 , 98 .
3.
Ohkata K.
,
Nagai T.
,
Tomaru A.
, and
Hanafusa T.
(1986 ) J. Chem. Soc, Perkin Trans. 2 , 43 .
4.
Martinez R.D.
,
Mancini P.M.E.
,
Voltero L.R.
, and
Nudleman N.S.
(1986 ) J. Chem. Soc., Perkin Trans. 2 , 1427 .
5.
Manikyamba P.
, and
Sundaram E.V.
(1990 ) Int. J. Chem. Kinetics , 22 , 1153 .
6.
Manikyamba P.
(1992 ) Indian J. Chem. , 31A , 959 .
7.
Manikyamba P.
(1996 ) Indian J. Chem. , 35A , 334 .
8.
Gholami M.R.
, and
Habibi Yangjeh A.
(2001 ) Int. J. Chem. Kinet. , 33 , 118 .
9.
Habibi Yangjeh A.
, and
Gholami M.R.
(2003 ) Indian J. Chem. , 42B , 895 .
10.
Ranga Reddy S.
, and
Manikyamba P.
(2004 ) Indian J. Chem. , 43A , 1092 .
11.
Kalyani P.
, and
Manikyamba P.
(2004 ) Indian J. Chem. , 43A , 76 .
12.
Ranga Reddy S.
, and
Manikyamba P.
(2006 ) Indian J. Chem. , 45A , 1844 .
13.
Winston J.S.
,
Jayaprakash Rao P.
,
Sethuram B.
, and
Navneeth Rao T.
(1996 ) Indian J. Chem. , 35A , 979 .
14.
Shanmuga Sundaram A.
, and
Raj Kumar M.
(1986 ) Indian J. Chem. , 25A , 71 .
15.
Harikishan B.
, and
Sundaram E.V.
(1989 ) J. Indian Chem. Soc. , 363 .
16.
Harikishan B.
, and
Sundaram E.V.
(1989 ) J. Indian Chem. , 28A , 793 .
17.
Harikishan B.
, and
Sundaram E.V.
(1980 ) J. Indian Chem. Soc. , 1079 .
18.
Frost A.A.
, and
Pearson R.G.
(1970 ) Kinetics and mechanism , p. 37 . Wiley Eastern , New Delhi .
19.
Shorter J.
(1982 ) Correlation analysis of organic reactivity , p. 21 . John Wiley & Sons, Research Studies Press , New York .
20.
Silverstein R.M.
,
Bassler G.C.
, and
Moill T.C.
(1981 ) Spectrometric identification of organic compounds , 4th edn, p. 190 . John Wiley & Sons , New York .
21.
Aslam M.H.
,
Collier G.
, and
Shorter J.
(1981 ) J. Chem. Soc., Perkin Trans. , 2 , 1572 .
22.
Taft R.W.
,
Abboud J.L.M.
,
Kamlet M.J.
, and
Abraham M.H.
(1983 ) J. Org. Chem. , 48 , 2877 .
23.
Weast R.C.
, and
Selby S.M.
(1967 ) Handbook of chemistry and physics , The Chemical Rubber Company , A , 165 .
24.International group for Correlation Analysis in Organic Chemistry (1985 ) (Announcement), Quant. Struct. Act. Relat. , 4 , 29 .