ABSTRACT
N-methylacetamide CH3CONHMe
N-(tert-butyl)-2,2-dimethyl propanamine tBuCONHtBu
acetohydrazide MeCONHNH2
benzenecarbohydrazide PhCONHNH2
N-[(1E)-buta-1,3-dienyl]- benzamide PhCONHPh
benzenesulfonamide PhSO2NH2
hydrazinophenyl sulfone PhSO2NHNH2
ethanamidine CH3C(=NH)NH2
105.3
(1) 103.9 (2) 106.5
110.5
80.3
440.6
434.7 445.6
462.3
343.1
336.0
405.8
439.3
338.9
426.8
AOP
AOP
AOP
AOP
AOP
AOP
AOP
AOP
AOP
1994ZHA/BOR(e)
(1) 1990BOR/ZHA (2) 1995BOR/ZHA
1995BOR/ZHA
1997ZHA/BOR
1997ZHA/BOR
1991BOR/JI(b)
1997ZHA/BOR
1997ZHA/BOR
1991BOR/JI(b)
(continued)
BDEs The broken bonds
(boldface = (boldface =
recommended data; dissociated atom)
references in parentheses) Methods
∆fHo(R), kcal/mol (references in (kJ/mol) kcal/mol kJ/mol parentheses) References
benzenecarboxamidine PhC(=NH)NH2
diethyl(iminophenylmethyl)- amine PhC(=NH)NEt2
[(1Z)-2-aza-1,2-diphenylvinyl]phenylamine PhC(=NPh)NHPh
[((1Z)-2-aza-1,2-diphenylvinyl)amino]dimethylamine PhC(=NPh)NHNMe2
[imino(phenylamino)methyl]- phenylamine (PhNH)2C=NH
[(1E)-2-aza-1,2-diphenylvinyl(amino)amino]- dimethylamine PhC(NHNMe2)=NPh
(tert-butyl)phenylthioamine tBuNHSPh
phenyl-N-(phenylcarbonylamino)carboxamide PhCONHNHCOPh
84.7
87.1
89.3
426.8
497.9
384.9
355.6
384.9
354.4
364.4
373.6
AOP
AOP
AOP
AOP
AOP
AOP
AOP
AOP
1991BOR/JI(b)
1991BOR/JI(b)
1991BOR/JI(b)
1991BOR/JI(b)
1991BOR/JI(b)
1992BOR/JI
1998BOR/LIU
1997ZHA/BOR
amine, substituted
Y = H
Y = 2,4-(NO2)2
Y = 2,4,6-(NO2)3
phenylphenylthioamine, substituted
Y = H
Y = Br
Y = MeO
Y = CN
phenyl(phenylsulfonyl)- amine, substituted
Y = H
Y = Br
Y = MeO
Y = CN
di-2-naphthamine (2-C10H7)2NH
hydrazines, substituted
81.1
83.1
82.6
83.0
81.6
84.2
93.2
94.4
89.1
96.6
86.1
339.3
347.7
334.7
345.6
347.3
341.4
352.3
389.9
395.0
372.8
404.2
360.2
AOP
AOP
AOP
Correlation
1997ZHA/BOR
1998BOR/LIU
1998BOR/LIU
2000DEN/DEN
BDEs The broken bonds
(boldface = (boldface =
recommended data; dissociated atom)
references in parentheses) Methods
∆fHo(R), kcal/mol (references in (kJ/mol) kcal/mol kJ/mol parentheses) References
Y = H
Y = p-Cl
Y = p-Me
Y = p-Et
Y = p-CF3
Y = p-CN
bis(1,1-dimethyl-1-silaethyl)- amine H-N(SiMe3)2
72.6
73.0
71.9
76.3
77.9
77.8
110.9
303.8
305.4
300.8
319.2
325.9
325.5
464.0
AOP
Derived
1997ZHA/BOR
1998BEC/WAL
7.1.2-N-H bonds in anilines Table 7.1.2 N-H BDEs in Anilines
BDEs The broken bonds
(boldface = (boldface =
recommended data; dissociated atom)
references in parentheses) Methods
∆fHo(R), kcal/mol (references in (kJ/mol) kcal/mol kJ/mol parentheses) References
Aniline or benzenamine PhNH-H ∆fHo(R) = 58.4±1
(244.3±4.2)
anilines, monosubstituted
Y = 4-F
Y = 2-Cl
(1) 88.0±2.0 (2) 92.3 (3) 89.1 (4) 92.2 in sol. (4) 89.7 in gas
(3) 88.8 in gas (3) 91.3 in sol.