SUPPORTING INFORMATION
Electronic structure and gas-phase chemistry of protonated α- and βquinonoid compounds: a mass spectrometry and computational study
Ricardo Vessecchi1*, Flávio S. Emery2, Norberto P. Lopes1 and Sérgio E.
Galembeck3
1
Núcleo de Pesquisa em Produtos Naturais e Sintéticos, Departamento de Física e
Química, Faculdade de Ciências Farmacêuticas de Ribeirão Preto, Universidade de São
Paulo, Brasil
2
Departamento de Ciências Farmacêuticas, Faculdade de Ciências Farmacêuticas de
Ribeirão Preto, Universidade de São Paulo, Brasil
3
Departamento de Química, Faculdade de Filosofia, Ciências e Letras de Ribeirão Preto,
Universidade de São Paulo, Brasil
*Correspondence to: R. Vessecchi, Núcleo de Pesquisa em Produtos Naturais e
Sintéticos (NPPNS), Departamento de Física e Química, Faculdade de Ciências
Farmacêuticas de Ribeirão Preto, Universidade de São Paulo, Via do Café, S/N – CEP,
14040-903,Ribeirão Preto/SP, Brasil.
E-mail: vessecchi@bol.com.br; vessecchi@usp.br
Table S1. Bond lengths (in Å) for (1) obtained using the B3LYP/6-31+G(d,p) model. * Values are
experimental
Bond
C(1)-C(2)
C(2)-C(3)
C(3)-C(4)
C(4)-C(4a)
C(5)-C(4a)
C(6)-C(5)
C(7)-C(6)
C(8)-C(7)
C(8)-C(8a)
C(1)-C(8a)
C(4a)-C(8a)
C(1)-O(1)
C(4)-O(2)
(1)
(1)*
1.485
1.478
1.345
1.340
1.485
1.478
1.493
1.468
1.400
1.393
1.395
1.383
1.401
1.401
1.395
1.383
1.400
1.393
1.493
1.468
1.411
1.407
1.227
1.223
1.227
1.223
*P. J. Gaultier, C. Hauw. Structure de 1'α-naphthoquinone. Acta Crystallogr. 1965, 18, 179. K. E. Wise,
A. K. Grafton, R. A. Wheeler. Trimethyl-p-benzoquinone provides excellent structural, spectroscopic,
and thermochemical models for plastoquinone-1 and its radical anion. J. Phys. Chem A 1997, 101, 1160.
Table S2. MK atomic charges, in arbitrary units
Atom
O(1)
O(2)
C(2)
C(3)
O(3)
(1)
–0.508794
–0.508791
–0.248312
–0.248288
-
(2)
–0.463437
–0.480321
(3)
–0.484332
–0.533613
(4)
–0.465186
–0.354924
–0.324233
-
–0.313059
–0.459434
–0.217891
–0.490405
O1
C7
C8
C8a
(A)
C6
C5
C4a
C1
(B)
C4
H
C2
C3
H
O2
Figure S1. Atom labels for 1,4- and 1,2-naphthoquinone.
ESI-MS/MS data
Intens.
+MS2(159.0000), 0eV, 11.3min #215
3000
159.0456
2000
1000
106.9919
0
116.9766
+MS2(159.0000), 5eV, 11.7min #221
3000
159.0452
2000
1000
106.9922
116.9760
131.0497
0
+MS2(159.0000), 10eV, 11.9min #225
600
159.0446
131.0491
400
106.9922
200
116.9764
72.9896
0
1000
+MS2(159.0000), 15eV, 12.2min #231
750
103.0554
500
131.0492
72.9906
250
159.0455
0
+MS2(159.0000), 20eV, 12.4min #236
600
103.0546
400
72.9912
77.0419
200
0
+MS2(159.0000), 25eV, 12.6min #239
600
77.0424
400
103.0526
200
72.9914
0
1000
+MS2(159.0000), 30eV, 12.9min #244
750
77.0427
500
250
103.0542
0
+MS2(159.0000), 35eV, 13.2min #250
800
600
77.0420
400
200
0
+MS2(159.0000), 40eV, 13.5min #256
600
77.0435
400
200
0
60
80
100
Figure S2. ESI-MS/MS spectra for [(1)+H]+.
120
140
160
m/z
Intens.
x10 4
+MS2(159.0000), 0eV, 8.9min #171
1.0
159.0444
0.5
131.0487
0.0
x10 4
+MS2(159.0000), 5eV, 9.1min #174
0.75
159.0449
0.50
131.0494
0.25
106.9919
0.00
+MS2(159.0000), 10eV, 9.3min #178
4000
131.0493
159.0432
2000
103.0545
0
116.9756
+MS2(159.0000), 15eV, 9.5min #183
4000
3000
131.0481
2000
103.0537
1000
159.0451
72.9896
0
+MS2(159.0000), 20eV, 9.9min #190
3000
103.0548
2000
131.0489
1000
77.0422
0
+MS2(159.0000), 25eV, 10.3min #198
2000
103.0546
77.0414
1000
131.0490
0
2000
+MS2(159.0000), 30eV, 10.9min #210
1500
77.0429
1000
103.0546
500
131.0498
0
+MS2(159.0000), 35eV, 11.3min #217
2000
1500
77.0428
1000
500
103.0568
0
+MS2(159.0000), 40eV, 11.7min #224
2000
1500
77.0430
1000
500
103.0536
0
60
80
100
Figure S3. ESI-MS/MS spectra for [(2)+H]+.
120
140
160
m/z
Intens.
x10 5
+MS2(243.0961), 0eV, 11.1min #211
243.1018
1.0
0.5
225.0913
187.0406
0.0
x10 5
2.0
+MS2(243.0961), 5eV, 11.2min #213
243.1017
1.5
1.0
0.5
187.0404
0.0
x10 5
201.0575
225.0914
+MS2(243.0961), 10eV, 11.4min #217
0.75
243.1014
187.0400
0.50
0.25
201.0571
159.0444
0.00
x10 5
1.00
225.0911
+MS2(243.0961), 15eV, 11.7min #222
0.75
187.0396
0.50
243.1011
159.0441
0.25
201.0568
0.00
x10 4
225.0901
+MS2(243.0961), 20eV, 11.9min #226
6
187.0400
159.0444
4
2
0
x10 5
103.0540
131.0486
201.0577
225.0909
243.1013
+MS2(243.0961), 25eV, 12.0min #228
0.75
159.0444
0.50
187.0400
0.25
0.00
x10 4
103.0540
131.0494
+MS2(243.0961), 30eV, 12.2min #232
6
159.0443
4
2
103.0537
131.0490
187.0400
0
x10 4
+MS2(243.0961), 35eV, 12.4min #236
3
159.0444
2
1
103.0534
131.0490
178.0781 187.0403
115.0551
0
x10 4
+MS2(243.0961), 40eV, 12.7min #240
1.5
1.0
103.0538
159.0447
0.5
131.0482
115.0535
0.0
100
120
178.0779
140
160
Figure S4. ESI-MS/MS spectra for [(3)+H]+.
180
200
220
240
m/z
Intens.
x10 5
2
+MS2(243.0970), 0eV, 13.9min #263
243.1011
1
0
x10 5
+MS2(243.0970), 5eV, 14.0min #265
3
243.1011
2
1
187.0396
0
x10 5
1.5
225.0908
+MS2(243.0970), 10eV, 14.2min #268
243.1008
1.0
187.0398
0.5
201.0563
159.0438
0.0
x10 5
225.0905
+MS2(243.0970), 15eV, 14.5min #273
1.0
187.0400
0.5
243.1013
159.0445
201.0570
0.0
x10 5
1.0
225.0912
+MS2(243.0970), 20eV, 14.7min #277
187.0393
159.0437
0.5
105.0329
0.0
x10 5
201.0576
225.0907
243.1010
+MS2(243.0970), 25eV, 14.9min #281
1.0
159.0436
0.5
187.0393
105.0330
131.0481
0.0
x10 5
+MS2(243.0970), 30eV, 15.2min #288
0.75
159.0437
0.50
0.25
103.0535
187.0393
131.0479
0.00
x10 4
+MS2(243.0970), 35eV, 15.5min #292
4
159.0442
103.0545
2
131.0488
77.0419
0
x10 4
4
187.0401
+MS2(243.0970), 40eV, 15.8min #298
3
103.0535
2
159.0438
1
77.0415
115.0535
0
60
80
100
120
131.0480
178.0776
140
Figure S5. ESI-MS/MS spectra for [(4)+H]+.
160
180
200
220
240
m/z
COMPUTATIONAL RESULTS
Geometries, vibrational frequencies and energies obtained using the B3LYP/6-31+G(d,p)
model
neutral
(1)
Charge = 0 Multiplicity = 1
C
0 -0.73907 -0.00021 0.13956
C
0 -0.72468 -0.00042 1.63275
C
0 0.60015 0.00008 2.30393
C
0 1.75277 0.00017 1.61129
C
0 1.78184 -0.00021 0.12641
C
0 0.47008 -0.00011 -0.58709
C
0 0.44114 0.00007 -1.98668
C
0 -0.78104 0.00014 -2.65919
C
0 -1.9815 0.00004 -1.93777
C
0 -1.96136 -0.00013 -0.5429
O
0 2.85346 0.00034 -0.47209
O
0 -1.75608 -0.00005 2.29816
H
0 0.57538 0.00032 3.39008
H
0 2.72349 0.00049 2.09915
H
0 1.38287 0.00014 -2.52567
H
0 -0.80057 0.00027 -3.74498
H
0 -2.93105 0.0001 -2.46471
H
0 -2.87929 -0.00022 0.03566
Zero-point correction=
0.132506 (Hartree/Particle)
Thermal correction to Energy=
0.141206
Thermal correction to Enthalpy=
0.142150
Thermal correction to Gibbs Free Energy=
0.098387
Sum of electronic and zero-point Energies=
-535.014120
Sum of electronic and thermal Energies=
-535.005420
Sum of electronic and thermal Enthalpies=
-535.004476
Sum of electronic and thermal Free Energies=
-535.048239
(2)
Charge = 0 Multiplicity = 1
c
c
1 cc2
c
2 cc3
1 ccc3
c
3 cc4
2 ccc4 1 dih4 0
c
4 cc5
3 ccc5 2 dih5 0
c
1 cc6
2 ccc6 3 dih6 0
c
4 cc7
3 ccc7 2 dih7 0
c
7 cc8
4 ccc8 3 dih8 0
c
8 cc9
7 ccc9 4 dih9 0
c
5 cc10 4 ccc10 3 dih10 0
o
10 oc11 5 occ11 4 dih11 0
o
9 oc12 8 occ12 7 dih12 0
h
1 hc13 2 hcc13 3 dih13 0
h
2 hc14 1 hcc14 6 dih14 0
h
3 hc15 2 hcc15 1 dih15 0
h
6 hc16 1 hcc16 2 dih16 0
h
7 hc17 4 hcc17 3 dih17 0
h
8 hc18 7 hcc18 4 dih18 0
Variables:
cc2
1.39817
cc3
1.39716
ccc3
cc4
ccc4
dih4
cc5
ccc5
dih5
cc6
ccc6
dih6
cc7
ccc7
dih7
cc8
ccc8
dih8
cc9
ccc9
dih9
cc10
ccc10
dih10
oc11
occ11
dih11
oc12
occ12
dih12
hc13
hcc13
dih13
hc14
hcc14
dih14
hc15
hcc15
dih15
hc16
hcc16
dih16
hc17
hcc17
dih17
hc18
hcc18
dih18
120.229
1.40205
120.56
0.
1.41574
118.929
0.
1.39659
119.832
0.
1.46248
120.729
-180.
1.35118
123.513
179.997
1.4689
121.302
0.
1.48918
119.925
179.999
1.21755
122.911
-179.994
1.21992
123.006
-179.992
1.08557
120.146
180.
1.08589
120.061
180.
1.08662
119.989
180.
1.08526
121.218
-180.
1.08797
116.829
-0.002
1.08563
122.012
-179.999
Zero-point correction=
0.132289 (Hartree/Particle)
Thermal correction to Energy=
0.141031
Thermal correction to Enthalpy=
0.141975
Thermal correction to Gibbs Free Energy=
0.097926
Sum of electronic and zero-point Energies=
-535.002483
Sum of electronic and thermal Energies=
-534.993741
Sum of electronic and thermal Enthalpies=
-534.992797
Sum of electronic and thermal Free Energies=
-535.036845
(3)
Charge = 0 Multiplicity = 1
c
c
c
c
c
c
c
c
c
c
o
o
c
c
c
o
c
c
h
h
h
h
h
h
h
h
h
h
h
h
h
h
1 cc2
2 cc3
1 ccc3
3 cc4
2 ccc4 1 dih4 0
4 cc5
3 ccc5 2 dih5 0
1 cc6
2 ccc6 3 dih6 0
4 cc7
3 ccc7 2 dih7 0
7 cc8
4 ccc8 3 dih8 0
8 cc9
7 ccc9 4 dih9 0
5 cc10 4 ccc10 3 dih10 0
10 oc11 5 occ11 4 dih11 0
7 oc12 4 occ12 3 dih12 0
8 cc13 7 ccc13 4 dih13 0
13 cc14 8 ccc14 7 dih14 0
14 cc15 13 ccc15 8 dih15 0
9 oc16 8 occ16 7 dih16 0
15 cc17 14 ccc17 13 dih17 0
15 cc18 14 ccc18 13 dih18 0
1 hc19 2 hcc19 3 dih19 0
2 hc20 1 hcc20 6 dih20 0
3 hc21 2 hcc21 1 dih21 0
6 hc22 1 hcc22 2 dih22 0
13 hc23 8 hcc23 7 dih23 0
13 hc24 8 hcc24 7 dih24 0
14 hc25 13 hcc25 8 dih25 0
14 hc26 13 hcc26 8 dih26 0
17 hc27 15 hcc27 14 dih27 0
17 hc28 15 hcc28 14 dih28 0
17 hc29 15 hcc29 14 dih29 0
18 hc30 15 hcc30 14 dih30 0
18 hc31 15 hcc31 14 dih31 0
18 hc32 15 hcc32 14 dih32 0
Variables:
cc2
1.39987
cc3
1.39597
ccc3
120.206
cc4
1.3981
ccc4
120.036
dih4
-0.07
cc5
1.40714
ccc5
119.737
dih5
0.003
cc6
1.39499
ccc6
120.062
dih6
0.055
cc7
1.49717
ccc7
119.712
dih7
179.509
cc8
1.47114
ccc8
118.668
dih8
179.795
cc9
1.36393
ccc9
120.695
dih9
-0.659
cc10
1.48967
ccc10
120.557
dih10
-179.646
oc11
1.22273
occ11
122.337
dih11
179.998
oc12
1.23283
occ12
dih12
cc13
ccc13
dih13
cc14
ccc14
dih14
cc15
ccc15
dih15
oc16
occ16
dih16
cc17
ccc17
dih17
cc18
ccc18
dih18
hc19
hcc19
dih19
hc20
hcc20
dih20
hc21
hcc21
dih21
hc22
hcc22
dih22
hc23
hcc23
dih23
hc24
hcc24
dih24
hc25
hcc25
dih25
hc26
hcc26
dih26
hc27
hcc27
dih27
hc28
hcc28
dih28
hc29
hcc29
dih29
hc30
hcc30
dih30
hc31
hcc31
dih31
hc32
120.704
-0.361
1.50504
118.536
178.407
1.53253
110.215
-162.319
1.53659
112.119
-45.253
1.34015
124.975
-178.802
1.53378
112.823
-63.443
1.52667
111.697
170.487
1.08596
120.065
-179.973
1.08608
119.984
-179.985
1.08488
121.445
179.844
1.08496
121.375
179.957
1.0982
109.967
74.692
1.09454
109.107
-40.256
1.09518
110.809
-167.29
1.09671
109.529
74.824
1.09357
110.079
178.978
1.09332
111.832
58.744
1.09517
110.008
-61.479
1.09373
110.425
-175.273
1.09471
110.08
64.837
1.09387
hcc32
dih32
110.701
-55.287
Zero-point correction=
0.257000 (Hartree/Particle)
Thermal correction to Energy=
0.272007
Thermal correction to Enthalpy=
0.272951
Thermal correction to Gibbs Free Energy=
0.215373
Sum of electronic and zero-point Energies=
-805.503432
Sum of electronic and thermal Energies=
-805.488425
Sum of electronic and thermal Enthalpies=
-805.487481
Sum of electronic and thermal Free Energies=
-805.545059
(4)
Charge = 0 Multiplicity = 1
c
c
1 cc2
c
2 cc3
1 ccc3
c
3 cc4
2 ccc4 1 dih4 0
c
4 cc5
3 ccc5 2 dih5 0
c
1 cc6
2 ccc6 3 dih6 0
c
4 cc7
3 ccc7 2 dih7 0
c
7 cc8
4 ccc8 3 dih8 0
c
8 cc9
7 ccc9 4 dih9 0
c
5 cc10 4 ccc10 3 dih10 0
o
10 oc11 5 occ11 4 dih11 0
o
7 oc12 4 occ12 3 dih12 0
c
12 co13 7 coc13 4 dih13 0
c
13 cc14 12 cco14 7 dih14 0
c
8 cc15 7 ccc15 4 dih15 0
c
13 cc16 12 cco16 7 dih16 0
c
13 cc17 12 cco17 7 dih17 0
o
9 oc18 8 occ18 7 dih18 0
h
1 hc19 2 hcc19 3 dih19 0
h
2 hc20 1 hcc20 6 dih20 0
h
3 hc21 2 hcc21 1 dih21 0
h
6 hc22 1 hcc22 2 dih22 0
h
14 hc23 13 hcc23 12 dih23 0
h
14 hc24 13 hcc24 12 dih24 0
h
15 hc25 8 hcc25 7 dih25 0
h
15 hc26 8 hcc26 7 dih26 0
h
16 hc27 13 hcc27 12 dih27 0
h
16 hc28 13 hcc28 12 dih28 0
h
16 hc29 13 hcc29 12 dih29 0
h
17 hc30 13 hcc30 12 dih30 0
h
17 hc31 13 hcc31 12 dih31 0
h
17 hc32 13 hcc32 12 dih32 0
Variables:
cc2
1.39773
cc3
1.39722
ccc3
120.516
cc4
1.40115
ccc4
120.256
dih4
-0.259
cc5
1.41223
ccc5
119.111
dih5
0.231
cc6
1.39519
ccc6
119.604
dih6
cc7
ccc7
dih7
cc8
ccc8
dih8
cc9
ccc9
dih9
cc10
ccc10
dih10
oc11
occ11
dih11
oc12
occ12
dih12
co13
coc13
dih13
cc14
cco14
dih14
cc15
ccc15
dih15
cc16
cco16
dih16
cc17
cco17
dih17
oc18
occ18
dih18
hc19
hcc19
dih19
hc20
hcc20
dih20
hc21
hcc21
dih21
hc22
hcc22
dih22
hc23
hcc23
dih23
hc24
hcc24
dih24
hc25
hcc25
dih25
hc26
hcc26
0.052
1.47759
121.173
-179.898
1.36834
123.677
178.599
1.45769
120.285
1.899
1.48838
120.216
179.73
1.21789
122.56
-178.977
1.34869
112.764
-0.847
1.47237
119.805
-170.957
1.53475
108.936
-38.303
1.50638
121.342
-177.056
1.52671
104.255
-157.684
1.53336
107.367
84.282
1.22621
122.613
179.593
1.08572
120.275
-179.899
1.0861
120.024
179.969
1.0832
120.379
179.83
1.08517
121.387
-179.829
1.09681
108.168
-64.791
1.09529
108.969
179.127
1.09821
110.168
-106.649
1.09469
108.957
dih26
hc27
hcc27
dih27
hc28
hcc28
dih28
hc29
hcc29
dih29
hc30
hcc30
dih30
hc31
hcc31
dih31
hc32
hcc32
dih32
138.376
1.09453
109.983
-177.96
1.09396
110.758
62.093
1.09418
110.653
-58.295
1.09505
109.954
178.646
1.09383
110.225
59.194
1.09297
111.779
-61.193
Zero-point correction=
0.256946 (Hartree/Particle)
Thermal correction to Energy=
0.271981
Thermal correction to Enthalpy=
0.272925
Thermal correction to Gibbs Free Energy=
0.215188
Sum of electronic and zero-point Energies=
-805.495642
Sum of electronic and thermal Energies=
-805.480607
Sum of electronic and thermal Enthalpies=
-805.479663
Sum of electronic and thermal Free Energies=
-805.537399
protonated (most stable molecules)
(1)
Charge = 1 Multiplicity = 1
C,0,-0.7785788586,0.0006566307,0.1452696864
C,0,-0.7748746052,0.0010445924,1.6416738471
C,0,0.548725009,0.0001741654,2.3254962348
C,0,1.7024807702,-0.0009196945,1.6228449287
C,0,1.6726288241,-0.0012688247,0.1781627082
C,0,0.44802345,-0.0004966499,-0.5769709133
C,0,0.4219191166,-0.0008428626,-1.9887942614
C,0,-0.7936917236,-0.0000627966,-2.6653843857
C,0,-1.9940093511,0.0010681043,-1.9448292528
C,0,-1.9860788257,0.0014273207,-0.54218405
O,0,2.8608797634,-0.0023863703,-0.3657684667
O,0,-1.8040372548,0.0020306282,2.2959080569
H,0,0.5326515531,0.0004632183,3.4112680519
H,0,2.6789818016,-0.0015713891,2.0966390933
H,0,1.3348686464,-0.0017118292,-2.5795916452
H,0,-0.8080007513,-0.000332919,-3.7498712668
H,0,-2.9408506963,0.0016743712,-2.4756056125
H,0,-2.9123198243,0.0023029443,0.0230791317
H,0,2.8606663684,-0.0026583707,-1.3387417263
Zero-point correction=
0.144814 (Hartree/Particle)
Thermal correction to Energy=
0.153812
Thermal correction to Enthalpy=
0.154756
Thermal correction to Gibbs Free Energy=
0.110411
Sum of electronic and zero-point Energies=
-535.331628
Sum of electronic and thermal Energies=
-535.322630
Sum of electronic and thermal Enthalpies=
-535.321686
Sum of electronic and thermal Free Energies=
-535.366032
(2)
Charge = 1 Multiplicity = 1
C,0,0.0028063594,0.0001113095,0.0056934106
C,0,-0.0016831862,0.0001761206,1.3987359723
C,0,1.2094978767,-0.0000161622,2.1070211643
C,0,2.4321651096,-0.0002855726,1.4160397057
C,0,2.4233917761,-0.0004831367,-0.0077071389
C,0,1.2201451252,-0.0001951035,-0.7045168159
C,0,3.6776950075,-0.000236367,2.1336140032
C,0,4.9295836959,-0.0000465726,1.5352320367
C,0,4.9809097903,-0.0001060431,0.143413851
C,0,3.7111404837,-0.0010574074,-0.7132969064
O,0,3.8855655156,0.0007952551,-1.9222638353
O,0,6.0944716522,0.0002023475,-0.5150737352
H,0,-0.9343781947,0.0002788645,-0.5412721551
H,0,-0.9414576263,0.0004209558,1.9407617529
H,0,1.2034946022,0.0001050317,3.1930998706
H,0,1.2285865112,-0.0003018284,-1.7899464235
H,0,3.6289428567,-0.0001039998,3.2202163706
H,0,5.8441372212,0.0001610243,2.1179921066
H,0,5.8932411557,-0.0001519533,-1.4829961481
Zero-point correction=
0.145162 (Hartree/Particle)
Thermal correction to Energy=
0.153950
Thermal correction to Enthalpy=
0.154894
Thermal correction to Gibbs Free Energy=
0.111200
Sum of electronic and zero-point Energies=
-535.339982
Sum of electronic and thermal Energies=
-535.331194
Sum of electronic and thermal Enthalpies=
-535.330250
Sum of electronic and thermal Free Energies=
-535.373944
(3)
C,0,-0.0159721158,0.0380166619,-0.0116947537
C,0,-0.014141723,0.059248613,1.3836337027
C,0,1.1948197206,0.0463609255,2.0848653712
C,0,2.4161000407,0.0119131975,1.3958109264
C,0,2.4031446592,-0.0129867065,-0.0194412632
C,0,1.1949366295,0.0017880698,-0.7131077386
C,0,3.707377336,0.0101687782,2.0856947464
C,0,4.9529351508,-0.0326252187,1.4404105905
C,0,4.9640327316,-0.0931384902,0.0473173093
C,0,3.6790229181,-0.0580894092,-0.7780171423
O,0,3.7403287986,-0.0719847067,-1.9901502953
O,0,3.7702710589,0.0492910291,3.4077439228
C,0,6.2559591751,-0.0057905447,2.2041198581
C,0,7.3939543543,0.4462746652,1.2787931998
C,0,7.4095184039,-0.2954607091,-0.0607873255
O,0,6.0315300049,-0.1790925211,-0.6778420857
C,0,7.676930597,-1.7959857253,0.0572937261
C,0,8.3170665482,0.3697826499,-1.086982167
H,0,-0.955342346,0.048095677,-0.5546016092
H,0,-0.9500713879,0.085555642,1.9314641317
H,0,1.1444354119,0.0625715957,3.171098287
H,0,1.2145915582,-0.0169335803,-1.7977304743
H,0,6.4594822373,-0.9962481864,2.6292452773
H,0,6.1731942483,0.6761911339,3.054801158
H,0,8.3601349507,0.2928678588,1.7681152897
H,0,7.3034038538,1.5210578506,1.0838096019
H,0,7.5977195378,-2.2766114227,-0.9208102917
H,0,6.983260623,-2.2900624423,0.7431058618
H,0,8.6933983977,-1.9488786934,0.432357826
H,0,8.2424336735,-0.1331629707,-2.0542182555
H,0,9.35440918,0.3079010348,-0.7449292637
H,0,8.0593494071,1.4240025836,-1.2184676362
H,0,2.9000432927,0.0880060478,3.8337553348
Zero-point correction=
0.269483 (Hartree/Particle)
Thermal correction to Energy=
0.284863
Thermal correction to Enthalpy=
0.285808
Thermal correction to Gibbs Free Energy=
0.227507
Sum of electronic and zero-point Energies=
-805.846720
Sum of electronic and thermal Energies=
-805.831339
Sum of electronic and thermal Enthalpies=
-805.830395
Sum of electronic and thermal Free Energies=
-805.888696
(4)
Charge = 1 Multiplicity = 1
C,0,-0.0076927687,-0.021087199,-0.0094371721
C,0,-0.0157847919,0.0368986723,1.3846790563
C,0,1.1863173838,0.0602601205,2.1029122672
C,0,2.4080717554,0.0218286527,1.4217898909
C,0,2.4098975159,-0.037507577,0.0067686778
C,0,1.2088616823,-0.0574591403,-0.7022213806
C,0,3.6861570368,0.0483286019,2.1504044431
C,0,4.956989031,-0.0139118333,1.5088874266
C,0,4.9561529687,-0.0628454486,0.1346661189
C,0,3.6943437313,-0.0765505411,-0.7024874424
O,0,3.8458643434,-0.1267510527,-1.9158282231
O,0,3.574761437,0.1320986234,3.4413615931
C,0,4.7650255159,0.2420271836,4.3838910693
C,0,5.9404529689,-0.5015612378,3.7496919533
C,0,6.2291914365,-0.0345853024,2.3190849267
C,0,4.2685571763,-0.4284701596,5.6575562002
C,0,4.9951821324,1.7406208571,4.5731002523
O,0,6.074578456,-0.1089546928,-0.5513278247
H,0,-0.9425589093,-0.0377999125,-0.5599079157
H,0,-0.9582640722,0.0649160056,1.9216462146
H,0,1.1728838323,0.1060440961,3.1853015356
H,0,1.2356938502,-0.1011473691,-1.7860438873
H,0,5.7227405157,-1.5758433459,3.7524720632
H,0,6.8212735031,-0.3544045453,4.3815088193
H,0,6.6884758909,0.9615338494,2.3129735698
H,0,6.9520793516,-0.701689758,1.8407534608
H,0,5.0548815145,-0.3812582203,6.4167198281
H,0,4.0239009868,-1.4796684053,5.4832593527
H,0,3.3854212909,0.0815941055,6.0507392055
H,0,5.7999744322,1.8880026438,5.299609679
H,0,4.0945994936,2.2221941603,4.9620699829
H,0,5.2811859269,2.2399664145,3.6437249111
H,0,5.8429185978,-0.1455319527,-1.5079017912
Zero-point correction=
0.269038 (Hartree/Particle)
Thermal correction to Energy=
0.284422
Thermal correction to Enthalpy=
0.285366
Thermal correction to Gibbs Free Energy=
0.226999
Sum of electronic and zero-point Energies=
-805.822335
Sum of electronic and thermal Energies=
-805.806952
Sum of electronic and thermal Enthalpies=
-805.806008
Sum of electronic and thermal Free Energies=
-805.864374