CCCBDB listing of experimental data page 2

Experimental data for C₆H₆ (Benzvalene)

Other names
Tricyclo[3.1.0.0^2,6]hex-3-ene; Tricyclo[2.1.1.0^5,6]hex-2-ene;

Other names

Tricyclo[3.1.0.0^2,6]hex-3-ene; Tricyclo[2.1.1.0^5,6]hex-2-ene;

INChI	INChIKey	SMILES	IUPAC name
InChI=1S/C6H6/c1-2-4-5-3(1)6(4)5/h1-6H/t3-,4+,5-,6+	VMQPMGHYRISRHO-FBXFSONDSA-N	[C@@H]12C=C[C@H]3[C@@H]1[C@@H]23	Tricyclo[3.1.0.0^2,6]hex-3-ene
InChI=1S/C6H6/c1-2-4-5-3(1)6(4)5/h1-6H/t3-,4+,5+,6-		[C@@H]12[C@H]3[C@H]1C=C[C@H]23	Tricyclo[3.1.0.0^2,6]hex-3-ene
InChI=1S/C6H6/c1-2-4-5-3(1)6(4)5/h1-6H	VMQPMGHYRISRHO-UHFFFAOYSA-N	C1=CC2C3C1C23	Tricyclo[3.1.0.0^2,6]hex-3-ene

INChI

INChIKey

SMILES

IUPAC name

InChI=1S/C6H6/c1-2-4-5-3(1)6(4)5/h1-6H/t3-,4+,5-,6+

VMQPMGHYRISRHO-FBXFSONDSA-N

[C@@H]12C=C[C@H]3[C@@H]1[C@@H]23

Tricyclo[3.1.0.0^2,6]hex-3-ene

InChI=1S/C6H6/c1-2-4-5-3(1)6(4)5/h1-6H/t3-,4+,5+,6-

[C@@H]12[C@H]3[C@H]1C=C[C@H]23

Tricyclo[3.1.0.0^2,6]hex-3-ene

InChI=1S/C6H6/c1-2-4-5-3(1)6(4)5/h1-6H

VMQPMGHYRISRHO-UHFFFAOYSA-N

C1=CC2C3C1C23

Tricyclo[3.1.0.0^2,6]hex-3-ene

State	Conformation
¹A₁	C2V

State

Conformation

¹A₁

C2V

Enthalpy of formation (Hfg), Entropy, Integrated heat capacity (0 K to 298.15 K) (HH), Heat Capacity (Cp)

Property	Value	Uncertainty	units	Reference	Comment

Information can also be found for this species in the NIST Chemistry Webbook

Vibrational levels (cm^-1) vibrations

Mode Number	Symmetry	Frequency			Intensity			Comment	Description
Mode Number	Symmetry	Fundamental(cm^-1)	Harmonic(cm^-1)	Reference	(km mol^-1)	unc.	Reference	Comment	Description
1	A₁	3103		1975Gri/Ken:1397
2	A₁	3081		1975Gri/Ken:1397
3	A₁	2995
4	A₁	1556
5	A₁	1376						authors label as uncertain
6	A₁	1367
7	A₁	1163
8	A₁	1090
9	A₁	972
10	A₁	996
11	A₁	656
12	A₂	1094						authors label as uncertain
13	A₂	910
14	A₂	800						authors label as uncertain
15	A₂	774						authors label as uncertain
16	A₂	536
17	B₁	3086
18	B₁	1101						authors label as uncertain
19	B₁	761						authors label as uncertain
20	B₁	742
21	B₁	628
22	B₁	500
23	B₂	3085
24	B₂	3071
25	B₂	1315
26	B₂	1241
27	B₂	1184
28	B₂	975						authors label as uncertain
29	B₂	850
30	B₂	812

vibrational zero-point energy: 20910.0 cm^-1 (from fundamental vibrations)
Calculated vibrational frequencies for C₆H₆ (Benzvalene).

Rotational Constants (cm^-1)

See section I.F.4 to change rotational constant units

A	B	C	reference	comment
0.24648	0.17599	0.12975	NISThydrocarbon

Calculated rotational constants for C₆H₆ (Benzvalene).

Product of moments of inertia
851195.5	amu³Å⁶		3.897600361026E-114	gm³ cm⁶

Geometric Data
picture of Benzvalene

Point Group C_2v

Internal coordinates
distances (r) in Å, angles (a) in degrees, dihedrals (d) in degrees

Description	Value	unc.	Connectivity				Reference	Comment
Description	Value	unc.	Atom 1	Atom 2	Atom 3	Atom 4	Reference	Comment
rCC	1.452	0.001	1	2			1973Sue/Har:4506
rCC	1.529	0.003	1	3			1973Sue/Har:4506
rCC	1.503	0.006	3	5			1973Sue/Har:4506
rCC	1.339	0.001	5	6			1973Sue/Har:4506
rCH	1.078	0.001	1	7			1973Sue/Har:4506
rCH	1.082	0.001	3	9			1973Sue/Har:4506
rCH	1.078	0.001	5	11			1973Sue/Har:4506
acch	133.7	0.1	1	2	8		1973Sue/Har:4506
aCCH	135.3	0.1	3	1	7		1973Sue/Har:4506
aCCH	119.8	0.3	1	3	9		1973Sue/Har:4506
aCCH	124.2	0.3	5	3	9		1973Sue/Har:4506
aCCH	125.4	0.1	3	5	11		1973Sue/Har:4506
aCCH	128.9	0.1	5	6	12		1973Sue/Har:4506
aCCC	105.7	0.1	3	5	6		1973Sue/Har:4506

Cartesians

Atom	x (Å)	y (Å)	z (Å)
C1	1.0122	0.0000	0.7261
C2	1.0122	0.0000	-0.7261
C3	0.1971	-1.0754	0.0000
C4	0.1971	1.0754	0.0000
C5	-1.2436	-0.6697	0.0000
C6	-1.2436	0.6697	0.0000
H7	1.7914	0.0000	1.4706
H8	1.7914	0.0000	-1.4706
H9	0.5467	-2.1019	0.0000
H10	0.5467	2.1019	0.0000
H11	-2.0832	-1.3465	0.0000
H12	-2.0832	1.3465	0.0000

Atom - Atom Distances bond lengths

Distances in Å

	C1	C2	C3	C4	C5	C6	H7	H8	H9	H10	H11	H12
C1		1.4522	1.5323	1.5323	2.4626	2.4626	1.0777	2.3308	2.2720	2.2720	3.4528	3.4528
C2	1.4522		1.5323	1.5323	2.4626	2.4626	2.3308	1.0777	2.2720	2.2720	3.4528	3.4528
C3	1.5323	1.5323		2.1508	1.4967	2.2630	2.4209	2.4209	1.0844	3.1965	2.2964	3.3265
C4	1.5323	1.5323	2.1508		2.2630	1.4967	2.4209	2.4209	3.1965	1.0844	3.3265	2.2964
C5	2.4626	2.4626	1.4967	2.2630		1.3394	3.4384	3.4384	2.2927	3.2996	1.0784	2.1840
C6	2.4626	2.4626	2.2630	1.4967	1.3394		3.4384	3.4384	3.2996	2.2927	2.1840	1.0784
H7	1.0777	2.3308	2.4209	2.4209	3.4384	3.4384		2.9411	2.8513	2.8513	4.3576	4.3576
H8	2.3308	1.0777	2.4209	2.4209	3.4384	3.4384	2.9411		2.8513	2.8513	4.3576	4.3576
H9	2.2720	2.2720	1.0844	3.1965	2.2927	3.2996	2.8513	2.8513		4.2039	2.7363	4.3368
H10	2.2720	2.2720	3.1965	1.0844	3.2996	2.2927	2.8513	2.8513	4.2039		4.3368	2.7363
H11	3.4528	3.4528	2.2964	3.3265	1.0784	2.1840	4.3576	4.3576	2.7363	4.3368		2.6929
H12	3.4528	3.4528	3.3265	2.2964	2.1840	1.0784	4.3576	4.3576	4.3368	2.7363	2.6929

Calculated geometries for C₆H₆ (Benzvalene).

Experimental Bond Angles (degrees) from cartesians

atom1	atom2	atom3	angle	atom1	atom2	atom3	angle
C1	C2	C3	61.716	C1	C2	C4	61.716
C1	C2	H8	133.693	C1	C3	C2	56.569
C1	C3	C5	108.771	C1	C3	H9	119.528
C1	C4	C2	56.569	C1	C4	C6	108.771
C1	C4	H10	119.528	C2	C1	C3	61.716
C2	C1	C4	61.716	C2	C1	H7	133.693
C2	C3	C5	108.771	C2	C3	H9	119.528
C2	C4	C6	108.771	C2	C4	H10	119.528
C3	C1	C4	89.143	C3	C1	H7	135.393
C3	C2	C4	89.143	C3	C2	H8	135.393
C3	C5	C6	105.727	C3	C5	H11	125.403
C4	C1	H7	135.393	C4	C2	H8	135.393
C4	C6	C5	105.727	C4	C6	H12	125.403
C5	C3	H9	124.534	C5	C6	H12	128.870
C6	C4	H10	124.534	C6	C5	H11	128.870

Bond descriptions

Examples: C-C single bond, C=C, double bond, C#C triple bond, C:C aromatic bond

Bond Type	Count
C-C	7
C=C	1
H-C	6

Connectivity

Atom 1	Atom 2
C1	C2
C1	C3
C1	C4
C1	H7
C2	C3
C2	C4
C2	H8
C3	C5
C3	H9
C4	C6
C4	H10
C5	C6
C5	H11
C6	H12

Electronic energy levels (cm^-1)

Energy (cm^-1)	Degeneracy	reference	description
0	1		¹A₁

Ionization Energies (eV)

Ionization Energy	I.E. unc.	vertical I.E.	v.I.E. unc.	reference
8.100		8.540		webbook

Dipole, Quadrupole and Polarizability
Electric dipole moment dipole

State	Config	State description	Conf description	Exp. min.	Dipole (Debye)				Reference	comment	Point Group	Components
State	Config	State description	Conf description	Exp. min.	x	y	z	total	Reference	comment	Point Group	dipole	quadrupole
1	1	¹A₁	C_2v	True			0.883	0.883	NISThydrocarbon		C_2v	1	2

Experimental dipole measurement abbreviations: MW microwave; DT Dielectric with Temperature variation; DR Indirect (usually an upper limit); MB Molecular beam
Calculated electric dipole moments for C₆H₆ (Benzvalene).
Electric quadrupole moment

State	Config	State description	Conf description	Exp. min.	Quadrupole (D Å)			Reference	comment	Point Group	Components
State	Config	State description	Conf description	Exp. min.	xx	yy	zz	Reference	comment	Point Group	dipole	quadrupole
1	1	¹A₁	C_2v	True						C_2v	1	2

Calculated electric quadrupole moments for C₆H₆ (Benzvalene).

References
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squib	reference	DOI
1973Sue/Har:4506	RD Suenram, MD Harmony "Microwave Structural Study of Benzvalene (Tricyclo[3.1.0.02,6]hex-3-ene)" J. Am. Chem. Soc. 95:14, 4506, 1973	10.1021/ja00795a007
1975Gri/Ken:1397	DWY Griffith, JE Kent, MF Odwyer "VIBRATIONAL-SPECTRA OF DEWAR BENZENE AND BENZVALENE" Aust. J. Chem. 28(7) 1397-1416, 1975	10.1071/CH9751397
NISThydrocarbon	NIST Hydrocarbon spectral database (http://www.physics.nist.gov/PhysRefData/MolSpec/Hydro/index.html)	10.18434/T4PC70
webbook	NIST Chemistry Webbook (http://webbook.nist.gov/chemistry)	10.18434/T4D303

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	Computational Chemistry Comparison and Benchmark DataBase Release 22 (May 2022) Standard Reference Database 101 National Institute of Standards and Technology
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Experimental data for C6H6 (Benzvalene)

Experimental data for C₆H₆ (Benzvalene)