Isotope effects in the reaction of benzo[h]quinoline N-oxides with methylsulfinyl carbanion examined by ab initio molecular orbital methods.
The reactions of benzo[h]quinoline N-oxide with methylsulfinyl carbanion and deuterated methylsulfinyl carbanion, respectively, were studied theoretically. Differences in yield between these reactions were explained using ab initio molecular orbital methods by considering the zero-point energy correction and the barrier penetration effect. In these reactions, two transition states affected the total reaction rate. The hydrogen- or deuterium-transfer step played a significant role, accounting for the difference in reaction rates.
Matsuzaki
Hisao
H
Tohoku Pharmaceutical University, 4-4-1 Komatsushima, Sendai 981-8558, Japan. matuzaki@tohoku-pharm.ac.jp
Saito
Koichi
K
Kobayashi
Akemi
A
Takeuchi
Isao
I
D016227:Benzoquinones / Q000032:analysis / Q000737:chemistry / Q000378:metabolism; D003497:Cyclic N-Oxides / Q000032:analysis* / Q000737:chemistry / Q000378:metabolism*; D007554:Isotopes; D008956:Models, Chemical; D011804:Quinolines / Q000032:analysis* / Q000737:chemistry / Q000378:metabolism*; D013463:Sulfuric Acid Esters / Q000032:analysis / Q000737:chemistry / Q000378:metabolism
D016227:Benzoquinones; D003497:Cyclic N-Oxides; D007554:Isotopes; D011804:Quinolines; D013463:Sulfuric Acid Esters; C033522:methyl sulfate