1997
DOI: 10.1039/a701902e
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Nucleophilic substitutions at the pyridine ring. Conformational preference of the products and kinetics of the reactions of 2-chloro-3-nitro- and 2-chloro-5-nitro-pyridines with arenethiolates †

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Cited by 33 publications
(30 citation statements)
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“…6 kJ. Previous kinetic results have confirmed that the transition state for ortho substitution is less extensively solvated than the transition for para substitution [2,16].…”
Section: The Ortho/para Ratiosupporting
confidence: 57%
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“…6 kJ. Previous kinetic results have confirmed that the transition state for ortho substitution is less extensively solvated than the transition for para substitution [2,16].…”
Section: The Ortho/para Ratiosupporting
confidence: 57%
“…Hence, in the absence of steric encumbrance, the activating power of a 6-nitro group is greater than that of a ring nitrogen. This was attributed to the more efficient delocalization of the negative charge with a nitro group than with a ring nitrogen in the transition state [2,16].…”
Section: Comparison Relative Activation Of a Ring Nitrogen And 6-nitrmentioning
confidence: 99%
See 1 more Smart Citation
“…This agrees with the rate determining formation of the zwitterionic intermediate I., Scheme 4. This is in line with the nucleophilic aromatic displacements of a good leaving group in polar and dipolar solvents (Khattab, Hamed, Albericio, & El-Faham, 2011;El-Mallah, Nabil, Senior, Ramadan, & Hamed, 2010;Asghar, Fathalla, & Hamed, 2009;Fathalla, Kassem, & Hamed, 2008;Khattab, Hassan, Hamed, & El-Faham, 2007;Al-Howsaway, Fathalla, El-Bardan, & Hamed, 2007;Fathalla & Hamed, 2006;Fathalla, Ibrahim, & Hamed, 2004;El-Hegazy, Abdel-Fathah, Hamed, & Sharaf, 2000;Hamed, El-Bardan, Saad, Gohar, & Hassan, 1997;Hamed, 1997aHamed, , 1997b. The plot of H # against log -S # for the reaction of 2 with hydrazine in MeOH, MeCN and DMSO gave straight line (r = 0.99) indicating a common mechanism for the reaction of 2 with hydrazine in these solvents.…”
Section: Reactions Of 1-chloro-24-dinitrobenzene 2 With Hydrazine Inmentioning
confidence: 54%
“…The present kinetic results shows difference in rates with changing in the nature of the leaving group from OBt to Cl, I, O-N = C(COOEt) 2 , O-N = C(CN)COOEt, O-N = C(CN) 2 [36,37,[51][52][53].…”
Section: Kinetics and The Reaction Mechanismmentioning
confidence: 99%