2
K. Yoshizawa and M. Miyanishi
Table 1 Various properties of methane and benzene
Methane
Benzene
Melting point (°C) a
−182.6
5.5
Boiling point (°C) a
−161.6
80.1
Density a
0.466 g m –3 (at −164 °C)
0.876 g cm −3 (at 20 °C)
Critical temperature (°C) b
−82.1
289
Critical pressure (atm) b
45.8
48.6
First ionization potential (eV)
13.2 c
9.23 d
Second ionization potential (eV) 19.4 c
17.2 e
First BDE (kcal mol −1 ) f
105.1 ± 2
110.9 ± 2
(Calcd. B3LYP/6-311++G**)
(kcal mol −1 )
103.0
110.4
Proton affinity (kcal mol −1 ) g
129.9
179.3
pKa h
48
43
Hº f
i
−17.9 kcal mol –1 (gas)
11.7 kcal mol −1 (liquid)
19.8 kcal mol −1 (gas)
C–H bond length (Å)
1.085 j
1.085 k
(Calcd. B3LYP/6-311++G**)
(Å)
1.091
1.084
C-13 NMR shift (ppm) l
−2.3
128.5
J(C–H) (Hz) l
125
158
Vibrational frequencies m,n
1306 cm –1 (degenerate
deformation)
1534 cm –1 (degenerate
deformation)
2917 cm –1 (symmetrical
stretching)
3019 cm –1 (degenerate
stretching)
674 cm –1 (CH bending)
1038 cm –1 (CH bending)
1479 cm –1 (ring streching,
deforming)
3036 cm –1 (CH streching)
3072 cm –1 (CH streching)
3091 cm –1 (CH streching)
a Kaye GWC, Laby TH (1973) Tables of physical and chemical constants. Longman, London
b Kobe KA, Lynn RE (1953) Chem Rev 52:117–236
c Frost J, McDowell P (1957) Proc Roy Soc A 241:194–207
d Arimura M, Yoshikawa Y (1984) Journal of the Mass Spectrometry Society of Japan 32:375–380
e Hustruid A, Kusch P, Tate JT (1938) Phys Rev 54:1037–1044
f Mamillen DF, Golden DM (1982) Ann Rev Chem 33:493–532
g Hunter EPL, Lias SG (1998) J Phys Ref Data 27:413–656
h pKa Data Compiled by R. Williams
i Atkins PW(1998) Atkins’ physical chemistry. Oxword University Press, New York
j Kuchitsu K, Bartell LS (1962) J Chem Phys 36:2470–2481
k Moe OLE, Stand TG (1985) J molec Struct 128:13–19
l Hesse M, Meier H, Zeeh B (1997) Spectroscopic Methods in Organic Chemistry. Georg Thieme
Verlag, Stuttgart
m Shimanouchi T(1972) Tables of Molecular Vibrational Frequencies. Consolidated Volume 1,
NSRDS NBS-39
n SDBSWeb: https://sdbs.db.aist.go.jp (National Institute of Advanced Industrial Science and
Technology, 2019. 2)
K. Yoshizawa and M. Miyanishi
Table 1 Various properties of methane and benzene
Methane
Benzene
Melting point (°C) a
−182.6
5.5
Boiling point (°C) a
−161.6
80.1
Density a
0.466 g m –3 (at −164 °C)
0.876 g cm −3 (at 20 °C)
Critical temperature (°C) b
−82.1
289
Critical pressure (atm) b
45.8
48.6
First ionization potential (eV)
13.2 c
9.23 d
Second ionization potential (eV) 19.4 c
17.2 e
First BDE (kcal mol −1 ) f
105.1 ± 2
110.9 ± 2
(Calcd. B3LYP/6-311++G**)
(kcal mol −1 )
103.0
110.4
Proton affinity (kcal mol −1 ) g
129.9
179.3
pKa h
48
43
Hº f
i
−17.9 kcal mol –1 (gas)
11.7 kcal mol −1 (liquid)
19.8 kcal mol −1 (gas)
C–H bond length (Å)
1.085 j
1.085 k
(Calcd. B3LYP/6-311++G**)
(Å)
1.091
1.084
C-13 NMR shift (ppm) l
−2.3
128.5
J(C–H) (Hz) l
125
158
Vibrational frequencies m,n
1306 cm –1 (degenerate
deformation)
1534 cm –1 (degenerate
deformation)
2917 cm –1 (symmetrical
stretching)
3019 cm –1 (degenerate
stretching)
674 cm –1 (CH bending)
1038 cm –1 (CH bending)
1479 cm –1 (ring streching,
deforming)
3036 cm –1 (CH streching)
3072 cm –1 (CH streching)
3091 cm –1 (CH streching)
a Kaye GWC, Laby TH (1973) Tables of physical and chemical constants. Longman, London
b Kobe KA, Lynn RE (1953) Chem Rev 52:117–236
c Frost J, McDowell P (1957) Proc Roy Soc A 241:194–207
d Arimura M, Yoshikawa Y (1984) Journal of the Mass Spectrometry Society of Japan 32:375–380
e Hustruid A, Kusch P, Tate JT (1938) Phys Rev 54:1037–1044
f Mamillen DF, Golden DM (1982) Ann Rev Chem 33:493–532
g Hunter EPL, Lias SG (1998) J Phys Ref Data 27:413–656
h pKa Data Compiled by R. Williams
i Atkins PW(1998) Atkins’ physical chemistry. Oxword University Press, New York
j Kuchitsu K, Bartell LS (1962) J Chem Phys 36:2470–2481
k Moe OLE, Stand TG (1985) J molec Struct 128:13–19
l Hesse M, Meier H, Zeeh B (1997) Spectroscopic Methods in Organic Chemistry. Georg Thieme
Verlag, Stuttgart
m Shimanouchi T(1972) Tables of Molecular Vibrational Frequencies. Consolidated Volume 1,
NSRDS NBS-39
n SDBSWeb: https://sdbs.db.aist.go.jp (National Institute of Advanced Industrial Science and
Technology, 2019. 2)