The nitro anomaly and Brønsted βnuc values in SN2 reactions on chlorine

Linoam Eliad, Shmaryahu Hoz

Research output: Contribution to journalArticlepeer-review

14 Scopus citations


The kinetics of chlorine transfer reactions between N-chlorosuccinimide (NCS) and four carbon nucleophiles (the conjugated bases of phenyldinitromethane, Meldrum's acid, phenylmalononitrile and phenylnitro-methane) in water were determined. A plot of log k for the SN2 reactions vs the pKa of the first three conjugated acids of the nucleophiles gave a straight line with a slope (βnuc) of 1.8. The data point for the mononitro derivative, phenylnitromethane, deviates negatively from the line by 6.7 log units. This deviation is typical of proton transfer reactions and was recently shown to occur also in SN2 reactions on bromine.

Original languageEnglish
Pages (from-to)540-543
Number of pages4
JournalJournal of Physical Organic Chemistry
Issue number8
StatePublished - Aug 2002


  • Halophilic reactions
  • Nitro anomaly
  • S2 on chlorine


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