T3: Bond Energies

Last updated
Save as PDF

Page ID: 10929

\( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \)

\( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}} \)

\( \newcommand{\id}{\mathrm{id}}\) \( \newcommand{\Span}{\mathrm{span}}\)

( \newcommand{\kernel}{\mathrm{null}\,}\) \( \newcommand{\range}{\mathrm{range}\,}\)

\( \newcommand{\RealPart}{\mathrm{Re}}\) \( \newcommand{\ImaginaryPart}{\mathrm{Im}}\)

\( \newcommand{\Argument}{\mathrm{Arg}}\) \( \newcommand{\norm}[1]{\| #1 \|}\)

\( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\)

\( \newcommand{\Span}{\mathrm{span}}\)

\( \newcommand{\id}{\mathrm{id}}\)

\( \newcommand{\Span}{\mathrm{span}}\)

\( \newcommand{\kernel}{\mathrm{null}\,}\)

\( \newcommand{\range}{\mathrm{range}\,}\)

\( \newcommand{\RealPart}{\mathrm{Re}}\)

\( \newcommand{\ImaginaryPart}{\mathrm{Im}}\)

\( \newcommand{\Argument}{\mathrm{Arg}}\)

\( \newcommand{\norm}[1]{\| #1 \|}\)

\( \newcommand{\inner}[2]{\langle #1, #2 \rangle}\)

\( \newcommand{\Span}{\mathrm{span}}\) \( \newcommand{\AA}{\unicode[.8,0]{x212B}}\)

\( \newcommand{\vectorA}[1]{\vec{#1}} % arrow\)

\( \newcommand{\vectorAt}[1]{\vec{\text{#1}}} % arrow\)

\( \newcommand{\vectorB}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \)

\( \newcommand{\vectorC}[1]{\textbf{#1}} \)

\( \newcommand{\vectorD}[1]{\overrightarrow{#1}} \)

\( \newcommand{\vectorDt}[1]{\overrightarrow{\text{#1}}} \)

\( \newcommand{\vectE}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash{\mathbf {#1}}}} \)

\( \newcommand{\vecs}[1]{\overset { \scriptstyle \rightharpoonup} {\mathbf{#1}} } \)

\( \newcommand{\vecd}[1]{\overset{-\!-\!\rightharpoonup}{\vphantom{a}\smash {#1}}} \)

\(\newcommand{\avec}{\mathbf a}\) \(\newcommand{\bvec}{\mathbf b}\) \(\newcommand{\cvec}{\mathbf c}\) \(\newcommand{\dvec}{\mathbf d}\) \(\newcommand{\dtil}{\widetilde{\mathbf d}}\) \(\newcommand{\evec}{\mathbf e}\) \(\newcommand{\fvec}{\mathbf f}\) \(\newcommand{\nvec}{\mathbf n}\) \(\newcommand{\pvec}{\mathbf p}\) \(\newcommand{\qvec}{\mathbf q}\) \(\newcommand{\svec}{\mathbf s}\) \(\newcommand{\tvec}{\mathbf t}\) \(\newcommand{\uvec}{\mathbf u}\) \(\newcommand{\vvec}{\mathbf v}\) \(\newcommand{\wvec}{\mathbf w}\) \(\newcommand{\xvec}{\mathbf x}\) \(\newcommand{\yvec}{\mathbf y}\) \(\newcommand{\zvec}{\mathbf z}\) \(\newcommand{\rvec}{\mathbf r}\) \(\newcommand{\mvec}{\mathbf m}\) \(\newcommand{\zerovec}{\mathbf 0}\) \(\newcommand{\onevec}{\mathbf 1}\) \(\newcommand{\real}{\mathbb R}\) \(\newcommand{\twovec}[2]{\left[\begin{array}{r}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\ctwovec}[2]{\left[\begin{array}{c}#1 \\ #2 \end{array}\right]}\) \(\newcommand{\threevec}[3]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\cthreevec}[3]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \end{array}\right]}\) \(\newcommand{\fourvec}[4]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\cfourvec}[4]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \end{array}\right]}\) \(\newcommand{\fivevec}[5]{\left[\begin{array}{r}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\cfivevec}[5]{\left[\begin{array}{c}#1 \\ #2 \\ #3 \\ #4 \\ #5 \\ \end{array}\right]}\) \(\newcommand{\mattwo}[4]{\left[\begin{array}{rr}#1 \amp #2 \\ #3 \amp #4 \\ \end{array}\right]}\) \(\newcommand{\laspan}[1]{\text{Span}\{#1\}}\) \(\newcommand{\bcal}{\cal B}\) \(\newcommand{\ccal}{\cal C}\) \(\newcommand{\scal}{\cal S}\) \(\newcommand{\wcal}{\cal W}\) \(\newcommand{\ecal}{\cal E}\) \(\newcommand{\coords}[2]{\left\{#1\right\}_{#2}}\) \(\newcommand{\gray}[1]{\color{gray}{#1}}\) \(\newcommand{\lgray}[1]{\color{lightgray}{#1}}\) \(\newcommand{\rank}{\operatorname{rank}}\) \(\newcommand{\row}{\text{Row}}\) \(\newcommand{\col}{\text{Col}}\) \(\renewcommand{\row}{\text{Row}}\) \(\newcommand{\nul}{\text{Nul}}\) \(\newcommand{\var}{\text{Var}}\) \(\newcommand{\corr}{\text{corr}}\) \(\newcommand{\len}[1]{\left|#1\right|}\) \(\newcommand{\bbar}{\overline{\bvec}}\) \(\newcommand{\bhat}{\widehat{\bvec}}\) \(\newcommand{\bperp}{\bvec^\perp}\) \(\newcommand{\xhat}{\widehat{\xvec}}\) \(\newcommand{\vhat}{\widehat{\vvec}}\) \(\newcommand{\uhat}{\widehat{\uvec}}\) \(\newcommand{\what}{\widehat{\wvec}}\) \(\newcommand{\Sighat}{\widehat{\Sigma}}\) \(\newcommand{\lt}{<}\) \(\newcommand{\gt}{>}\) \(\newcommand{\amp}{&}\) \(\definecolor{fillinmathshade}{gray}{0.9}\)

The following tables list experimental bond dissociation enthalpies of common bonds at 298 K.

R-H bonds

**Inorganics**
Bond	\(\Delta{H_{298 }}\)(kcal.mol^-1)	\(\Delta{H_{298 }}\) (kJ.mol^-1)
H-H	104.2	436.0
H-F	136.3	570.3
H-Cl	103.2	431.8
H-Br	87.5	366.1
H-I	71.3	298.3
H-CN	126.3	528.4
H-NH₂	107.6	450.2
H-OH	118.8	497.1
H-SH	91.2	381.6
H-NO	49.5	207.1
H-ONO (trans)	79.1	331.0
H-ONO₂	101.7	425.5
H-SiH₃	91.7	383.7
H-GeH₃	83	347

**Hydrocarbons**
Bond	\(\Delta{H_{298 }}\)(kcal.mol^-1)	\(\Delta{H_{298 }}\) (kJ.mol^-1)
CH₃-H	105.0	439.3
CH₃CH₂-H	101.1	423.0
(CH₃)₂CH-H	98.6	412.5
CH₃CH₂(CH₃)CH-H	98.2	410.9
(CH₃)₃C-H	96.5	403.8
CH₂CH-H	110.7	463.2
CH₂CHCH₂-H	88.8	371.5
(CH₂CH)₂CH-H	76.4	319.7
HCC-H	133.3	557.7
C₆H₅-H	112.9	472.4
C₆H₅CH₂-H	89.8	375.7
C₅H₅-H	79.9	334.3
c-C₃H₅-H	105.7	442.2
c-C₄H₇-H	95.6	400.0
c-C₅H₉-H	93.0	389.1
c-C₆H₁₁-H	95.6	400.0
c-C₇H₁₃-H	93.4	390.8
-	-	-

**Halides**
Bond	\(\Delta{H_{298 }}\)(kcal.mol^-1)	\(\Delta{H_{298 }}\) (kJ.mol^-1)
H-CH₂F	101.3	423.8
H-CH₂Cl	99.5	416.3
H-CH₂Br	101.6	425.1
H-CF₃	106.7	446.4
H-CCl₃	95.8	400.8
H-CBr₃	96.0	401.7

**Alcohols**
Bond	\(\Delta{H_{298 }}\)(kcal.mol^-1)	\(\Delta{H_{298 }}\) (kJ.mol^-1)
CH₃O-H	104.6	437.6
H-CH₂OH	96.1	402.1
CH₃CH₂O-H	104.7	438.1
(CH₃)₂CHO-H	105.7	442.2
(CH₃)₃CO-H	106.3	444.8
C₆H₅O-H	90	377

**Peroxides**
Bond	\(\Delta{H_{298 }}\)(kcal.mol^-1)	\(\Delta{H_{298 }}\) (kJ.mol^-1)
HOO-H	87.8	367.4
CH₃OO-H	88	368
CH₃CH₂OO-H	85	356
(CH₃)₃COO-H	84	351

**Carbonyls**
Bond	\(\Delta{H_{298 }}\)(kcal.mol^-1)	\(\Delta{H_{298 }}\) (kJ.mol^-1)
HC(O)-H	88.1	368.6
CH₃C(O)-H	89.4	374.0
H-CH₂CHO	94	393
C₆H₅C(O)-H	88.9	372.0
HCOO-H	112	469
H-COOH	≥96	402
CH₃COO-H	112	469
H-CH₂COOH	96	402
C₆H₅COO-H	111	464

**Others**
Bond	\(\Delta{H_{298 }}\)(kcal.mol^-1)	\(\Delta{H_{298 }}\) (kJ.mol^-1)
CH₃S-H	87.4	365.7
H-CH₂SH	94	393
H-CH₂SO₂Me	99.0	414.2
H-CH₂NH₂	92.2	385.8
H-CH₂CN	93.4	390.8
CH₃CH₂O-CH₃	81	339

Blanksby, S. J.; Ellison, G. B. Acc. Chem. Res. 2003, 36 , 255.
Feng, Y.; Huang, H.; Liu, L.; Guo, Q.-X. Phys. Chem. Chem. Phys. 2003, 5, 685.
Zavitsas, A. A. J. Phys. Chem. A 2003, 107, 897.
McGivern, S. W.; Derecskei-Kovacs, A.; North, S. W.; Francisco, J. S. J. Phys Chem. A 2000, 104, 436.
Jursic, B. S. J. Chem. Soc. Perkin Trans. 1999, 2, 369.
Verevkin, S. P.; Krashnykh, E. L.; Wright, J. S. Phys. Chem. Chem. Phys. 2003, 5, 2605.

Enthalpy Change, Single Bonds (first half)
Single Bonds	ΔH°^*
H–H	104.2
C–C	83
N–N	38.4
O–O	35
F–F	36.6
Si–Si	52
P–P	50
S–S	54
Cl–Cl	58
Br–Br	46
I–I	36.
H–C	99
H–N	93
H–O	111
H–F	135
H–Cl	103
H–Br	87.5
H–I	71
H–B	90
H–S	81
H–Si	75
H–P	77

Enthalpy Change, Single Bonds (second half)
Single Bonds	ΔH°^*
B–F	150
B–O	125
C–N	73
N–CO	86
C–O	85.5
O–CO	110
C–S	65
C–F	116
C–Cl	81
C–Br	68
C–I	51
C–B	90
C–Si	76
C–P	70
N–O	55
S–O	87
Si–F	135
Si–Cl	90
Si–O	110
P–Cl	79
P–Br	65
P–O	90

Enthalpy Change, Multiple Bonds
Multiple Bonds	ΔH°^*
C=C	146
N=N	109
O=O	119
C=N	147
C=O (CO₂)	192
C=O (aldehyde)	177
C=O (ketone)	178
C=O (ester)	179
C=O (amide)	179
C=O (halide)	177
C=S (CS₂)	138
N=O (HONO)	143
P=O (POCl₃)	110
P=S (PSCl₃)	70
S=O (SO₂)	128
S=O (DMSO)	93
P=P	84
P≡P	117
C≡O	258
C≡C	200
N≡N	226
C≡N	213

Bond Dissociation Energies
atom or group	methyl	ethyl	i-propyl	t-butyl	phenyl	benzyl	allyl	acetyl	vinyl
H	103	98	95	93	110	85	88	87	112
F	110	110	109	-	124	94	-	119	-
Cl	85	82	81	80	95	68	70	82	90
Br	71	70	69	66	79	55	56	68	80
I	57	54	54	51	64	40	42	51	-
OH	93	94	92	91	111	79	82	107	-
NH₂	87	87	86	85	104	72	75	95	-
CN	116	114	112	-	128	100	-	-	128
CH₃	88	85	84	81	101	73	75	81	98
C₂H₅	85	82	81	78	99	71	72	78	95
(CH₃)₂CH	84	81	79	74	97	70	71	76	93
(CH₃)₃C	81	78	74	68	94	67	67	-	89
C₆H₅	101	99	97	94	110	83	87	93	108
C₆H₅CH₂	73	71	70	67	83	59	59	63	81

Many of the bond energies listed here were taken from the following sources:

R.T.Sanderson, Polar Covalence, 1983
R.T.Sanderson, Chemical Bonds and Bond Energy, 1976

William Reusch, Professor Emeritus (Michigan State U.), Virtual Textbook of Organic Chemistry

Template:HideTOC

Search

Text Color

Text Size

Margin Size

Font Type