ISSN:
0894-3230
Keywords:
Chemistry
;
Theoretical, Physical and Computational Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
Nucleophilic substitution reactions of (Z)-benzyl (X)-benzene sulfonates with (Y)-pyridines were investigated in acetone at 35°C. The magnitudes of the Hammett reaction constants ρX, ρY and ρZ indicate that a stronger nucleophile leads a lesser degree of bond breaking and a better leaving group is accompanied by a lesser degree of bond formation. The magnitude of interaction term, ρij, can be used to determine the structure of the transition state (TS) for the SN reaction. In particular, the comparison of ρXZ with ρYZ and the sign of ρZ can predict that this reaction series proceed via dissociative SN2 process. This result also accords with the treatment of the MOFJ diagram. The sign of the product ρXZρYZ can predict the movement of the TS.
Additional Material:
2 Ill.
Type of Medium:
Electronic Resource
