Rate-Product Correlations for the Solvolysis of 5-Nitro-2-Furoyl Chloride
- 1. Gyeongsang National Univ., Jinju (Korea, Republic of)
- 2. Jeonju National Univ. of Education, Jeonju (Korea, Republic of)
- 3. Univ. of Balochistan, Quetta (Pakistan)
Description
The solvolysis rate constants of 5-nitro-2-furoyl chloride (5-NO2(C4H2O)-2-COCl, 1) in 27 different solvents are well correlated with the extended Grunwald-Winstein equation, using the NT solvent nucleophilicity scale and YCl solvent ionizing scale, with sensitivity values of 1.20 ± 0.05 and 0.37 ± 0.02 for l and m, respectively. The activation enthalpies (ΔH≠) were 5.63 to 13.0 kcal·mol-1 and the activation entropies (ΔS≠) were -25.9 to -43.4 cal·mol-1·K-1, which is consistent with the proposed bimolecular reaction mechanism. The solvent kinetic isotope effect (SKIE, kMeOH/kMeOD) of 2.65 was also in accord with the SN2 mechanism and was possibly assisted using a general-base catalysis. The product selectivity (S) for solvolysis of 1 in alcohol/water mixtures was 1.2 to 11, which is also consistent with the proposed bimolecular reaction mechanism
Additional details
Publishing Information
- Journal Title
- Bulletin of the Korean Chemical Society
- Journal Volume
- 33
- Journal Issue
- 10
- Series
- 23 refs, 4 figs, 4 tabs
- Journal Page Range
- p. 3293-3297
- ISSN
- 0253-2964
INIS
- Country of Publication
- Korea, Republic of
- Country of Input or Organization
- Korea, Republic of
- INIS RN
- 45096370
- Subject category
- S37: INORGANIC, ORGANIC, PHYSICAL AND ANALYTICAL CHEMISTRY;
- Descriptors DEI
- CATALYSIS; CHLORIDES; CORRELATIONS; ENTHALPY; EQUATIONS; SOLVENTS; SOLVOLYSIS
- Descriptors DEC
- CHEMICAL REACTIONS; CHLORINE COMPOUNDS; DECOMPOSITION; HALIDES; HALOGEN COMPOUNDS; PHYSICAL PROPERTIES; THERMODYNAMIC PROPERTIES