Kinetic study of proton/deuteron transfer reactions of 2,4,6‐trinitrotoluene and its derivatives with tertiary amines

Yoshimi Sueishi, Takanori Fujimoto, Tohru Yoshida, Takeharu Kurita, Shunzo Yamamoto, Norio Nishimura

Research output: Contribution to journalArticle

4 Citations (Scopus)

Abstract

The rate of proton/deuteron transfer reactions of 2,4,6‐trinitrotoluene (TNT), 2,2′4,4′6,6′‐hexanitrobibenzyl (HNBB) and 2,4,6‐trinitrobenzyl chlorides (TNB) with tertiary amines was followed spectrophotometrically. The rate constants obtained under various conditions were interpreted in terms of isotope, solvent and steric effects. The Arrhenius plots curved upward at low temperatures for TNT and TNB, indicating clearly the intervention of tunnelling. The tunnelling parameteres were calculated semi‐empirically on the basis of Bell's theory. The observed rate constants at low temperatures agreed well with the predicted values. In the present systems, some side and consecutive reactions involving the formation of 2,2′,4,4′6,6′‐hexanitrostilbene took place, and in some cases interrupted the rate measurements in the proton/deuteron transfer steps.

Original languageEnglish
Pages (from-to)387-394
Number of pages8
JournalJournal of Physical Organic Chemistry
Volume8
Issue number6
DOIs
Publication statusPublished - 1995

ASJC Scopus subject areas

  • Physical and Theoretical Chemistry
  • Organic Chemistry

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