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.