ISSN:
0894-3230
Keywords:
Organic Chemistry
;
Physical Chemistry
Source:
Wiley InterScience Backfile Collection 1832-2000
Topics:
Chemistry and Pharmacology
,
Physics
Notes:
The Kinetics of reactions of phenacyl benzenesulphonates with benzylamines were investigated in methanol at 45·0 °C and the cross-interaction constants λXY, λYZ and βXZ were determined in order to elucidate the transition-state structure. The unusually small magnitude of λXY can only be accounted for by the resonance ‘shunt’ effect of the α-CO group of the phenacyl system. Large |λYZ| values indicate a small degree of bond breaking whereas relatively large |βXZ| values compared with those for the dissociative SN2 reaction indicate a relatively tight transition state for the reactions. Further, the similar magnitudes of βXZ values compared with those of the corresponding aniline nucleophile series suggest a similar transition-state structure for the two armatic amine nucleophile series.
Additional Material:
1 Ill.
Type of Medium:
Electronic Resource
URL:
http://dx.doi.org/10.1002/poc.610020607