C?H and N?H bond dissociation energies of five- and six-membered ring aromatic compounds

2003 ◽  
Vol 16 (12) ◽  
pp. 883-890 ◽  
Author(s):  
Yong Feng ◽  
Jin-Ti Wang ◽  
Lei Liu ◽  
Qing-Xiang Guo

The paper reports the effects of substituents on C— Br bond dissociation energy in substituted bromobenzenes. The following substituents introduced in various positions of benzene ring were investigated: F, Cl, Br, CH 3 , C 6 H 5 , CN and OH. In addition, the studies were extended to bromopyridines and bromothiophene. Assuming that the frequency factor is constant for the series of decompositions, the following values were obtained for the difference ∆ D = D ( Ph — Br) - D ( Ph s — Br), where Ph s Br denotes a molecule of substituted bromobenzene: substituent ∆D (kcal/mole) substituent ∆D (kcal/mole) p -F 0-5 m -C 6 H 5 0-8 p -Cl 0-6 o -C 6 H 5 2-7 m -Cl 1-0 p -CN 0-3 o -Cl 1-2 m -CN 0-8 p -Br 0-3 o -CN 0-6 o -Br 1-8 p -OH 3-9 P -CH 3 0-2 o -OH 3-8 m -CH 3 0-2 3-bromopyridine -5-0 o -CH 3 0-8 2-bromopyridine -0-6 p -C 6 H 5 0-2 2-bromothiophene 2-4 The significance of these results is discussed, and a tentative explanation of the observed effects is proposed.


2017 ◽  
Vol 417 ◽  
pp. 69-75 ◽  
Author(s):  
David Gatineau ◽  
Antony Memboeuf ◽  
Anne Milet ◽  
Richard B. Cole ◽  
Héloïse Dossmann ◽  
...  

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