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NO migration from N ‐methyl‐ N ‐nitrosobenzene‐sulfonamide to 3,6‐dibromocarbazole: Concerted or stepwise reaction path?
Author(s) -
Zhang Dongju,
Sun Hui,
Wang Fang,
Liu Chengbu
Publication year - 2007
Publication title -
international journal of quantum chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.484
H-Index - 105
eISSN - 1097-461X
pISSN - 0020-7608
DOI - 10.1002/qua.21299
Subject(s) - nitrosobenzene , sulfonamide , chemistry , concerted reaction , density functional theory , computational chemistry , ring (chemistry) , reaction mechanism , stepwise reaction , transition state , path (computing) , stereochemistry , catalysis , organic chemistry , physics , quantum mechanics , kinetics , reaction rate constant , order of reaction , computer science , programming language
The NO migration from N ‐methyl‐ N ‐nitrosobenzene‐sulfonamide to 3,6‐dibromocarbazole was proposed in a recent literature to follow a stepwise reaction path. However, the present density functional theory calculations at the MP2/6–31G(d,p)//B3LYP/6–31G(d,p) level show that this reaction exclusively proceeds via a concerted mechanism involving a four‐membered ring transition state. The calculated barrier is in good agreement with the experimental finding. © 2007 Wiley Periodicals, Inc. Int J Quantum Chem, 2007