Kinetics and mechanism of the  aminolysis  of bis(4‐nitrophenyl) carbonate and  O ‐(4‐nitropheny) S‐(4‐nitrophenyl) thio and dithiocarbonate | Zendy

Castro Enrique A. | Zendy; Aliaga Margarita E. | Zendy; Gazitúa Marcela | Zendy; Pavez Paulina | Zendy; Santos José G. | Zendy

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Kinetics and mechanism of the aminolysis of bis(4‐nitrophenyl) carbonate and O ‐(4‐nitropheny) S‐(4‐nitrophenyl) thio and dithiocarbonate

Author(s) -

Castro Enrique A.,

Aliaga Margarita E.,

Gazitúa Marcela,

Pavez Paulina,

Santos José G.

Publication year - 2014

Publication title -

journal of physical organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.325

H-Index - 66

eISSN - 1099-1395

pISSN - 0894-3230

DOI - 10.1002/poc.3231

Subject(s) - chemistry , aminolysis , morpholine , alicyclic compound , thio , carbonate , kinetics , medicinal chemistry , counterion , organic chemistry , reaction mechanism , catalysis , ion , physics , quantum mechanics

The kinetics of the reactions of secondary alicyclic amines with bis(4‐nitrophenyl) carbonate ( 1 ), S ‐(4‐nitrophenyl) O ‐(4‐nitrophenyl) thiocarbonate ( 2 ) and S ‐(4‐nitrophenyl) O ‐(4‐nitrophenyl) dithiocarbonate ( 3 ) were studied at 25.0 °C. The reactions of 1 were studied in water and those of 2 and 3 in 44 wt% ethanol–water. These reactions are concerted. The HPLC analyses of the reactions of 2 and 3 with morpholine show that both 4‐nitrophenoxide and 4‐nitrobenzenethiolate ions are the nucleofuges. Copyright © 2013 John Wiley & Sons, Ltd.

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