Supporting Information for
Photo-induced isomerization of ethylene-bridged azobenzene
explored by ab initio based non-adiabatic dynamics simulation: A
comparative investigation of the isomerization in the gas and solution
phases
Jun Cao, Li-hong Liu, and Wei-Hai Fang
Key Laboratory of Theoretical and Computational Photochemistry, Ministry of
Education; College of Chemistry, Beijing Normal University, Beijing 100875, China
Zhi-Zhong Xie
Department of Chemistry, School of Science, Wuhan University of Technology, Wuhan
430070, China
Yong Zhang*
Department of Chemistry, Chemical Biology, and Biomedical Engineering, Stevens
Institute of Technology, Castle Point on Hudson Hoboken, NJ 07030
1. Relative energies and geometry parameters for the critical structures in S0
and S1 states, which are calculated at different levels of theory and basis sets.
Energy is in kcal/mol, bond length in Å, and bond angle in degree.
The Z isomer
E
C5-N1-N2-C3
C6-C7-C8-C4
N1-N2
C5-N1
N2-C3
C5-N1-N2
N1-N2-C3
B3LYP/6-31G*
0
6.8
38.7
1.25
1.45
1.44
122.6
122.1
B3LYP/6-311+G**
0
6.6
37.7
1.24
1.45
1.44
122.5
122.0
B3LYP/cc-pVDZ
0
6.7
38.6
1.25
1.45
1.44
122.5
122.1
CAS(10,8)/6-31G*
0
6.0
32.3
1.24
1.44
1.44
121.5
121.1
CAS(6,4)/3-21G*
0
7.3
34.7
1.28
1.46
1.46
120.8
120.2
The E isomer
E
C5-N1-N2-C3
C6-C7-C8-C4
N1-N2
C5-N1
N2-C3
C5-N1-N2
N1-N2-C3
B3LYP/6-31G*
7.36
147.0
147.0
1.26
1.42
1.42
111.6
111.6
B3LYP/6-311+G**
6.85
146.9
146.9
1.25
1.42
1.42
112.2
112.2
B3LYP/cc-pVDZ
7.20
147.1
147.1
1.26
1.42
1.42
111.7
111.7
CAS(10,8)/6-31G*
7.9
147.5
95.8
1.25
1.42
1.42
111.1
111.1
CAS(6,4)/3-21G*
8.1
145.4
103.6
1.29
1.44
1.44
111.3
111.3
S1
The transition state (TS_EZ) between E and Z
E
B3LYP/6-31G*
B3LYP/6-311+G**
B3LYP/cc-pVDZ
CAS(10,8)/6-31G*
CAS(6,4)/3-21G*
a relative
to Z,
C5-N1-N2-C3
C6-C7-C8-C4
N1-N2
C5-N1
N2-C3
C5-N1-N2
N1-N2-C3
26.42
a
108.9
110.3
1.24
1.45
1.33
116.4
168.0
26.33
a
105.4
110.1
1.23
1.45
1.33
116.9
168.1
26.32
a
108.2
109.7
1.24
1.45
1.34
116.4
168.0
a
40.4 /32.5
b
94.1
110.0
1.23
1.45
1.36
117.5
163.9
a
b
111.8
114.5
1.25
1.47
1.37
115.2
172.2
30.9 /22.8
b relative
to E
Minimum-energy conical intersection (CI_E) between S1 and S0
Energy
C5-N1-N2-C3
C6-C7-C8-C4
N1-N2
C5-N1
N2-C3
C5-N1-N2
N1-N2-C3
CAS(10,8)/6-31G*
43.8
99.1
108.9
1.28
1.41
1.36
122.0
135.2
CAS(6,4)/3-21G*
47.0
99.5
114.5
1.33
1.44
1.41
121.3
131.8
A conical intersection (CI_Z) between S1 and S0
CAS(6,4)/3-21G*
a Relative
Energy
C5-N1-N2-C3
C6-C7-C8-C4
N1-N2
C5-N1
N2-C3
C5-N1-N2
N1-N2-C3
66.8a
86.0
32.9
1.34
1.48
1.42
103.2
126.8
to Z in ground state calculated at the CAS(6,4)/3-21G* level
2. Assessment of the QM/MM interaction energies.
According to the suggestion from one of reviewers, test calculations were
performed to assess the QM/MM interaction energies. The interaction energies
between QM and MM moieties were calculated with the combined QM/MM scheme
and a pure QM method. The pure QM calculations were performed at the
B3LYP/3-21G*, CAS(6,4)/aug-cc-pVTZ, and MP2/ aug-cc-pVTZ levels. For the
QM/MM calculations, the QM moiety is treated at the CAS(6,4)/3-21G* level and the
MM moiety is calculated using the OPLSAA force field. Four different clusters of
BAB-(CH3OH)2, BAB-(CH3OH)5, BAB-(CH3OH)11, and BAB-(CH3OH)60 were
selected for the QM/MM and pure QM calculations with two different BAB
geometric structures, referred to as QM1 and QM2. The clusters were selected from
different snapshots of the MD simulations with the E isomer fixed at the center of the
cavity. The corresponding cut-off radius is 5Å, 6Å, and 8Å for BAB-(CH3OH)5,
BAB-(CH3OH)11, and BAB-(CH3OH)60, respectively. When the QM moiety has
S2
different structure, the CH3OH molecules have different arrangement in space even
for the same size of the BAB-(CH3OH)n clusters (n=2, 5, 11, 60), since they come
from different snapshot. The calculated results are listed below.
The key bond parameters for two QM structures (QM1 and QM2)
QM1
QM2
N1-N2
1.29 Å
N1-N2
1.33 Å
C5-N1
1.44 Å
C5-N1
1.48 Å
N2-C3
1.44 Å
N2-C3
1.52 Å
C5-N1-N2-C3
145.4
C5-N1-N2-C3
149.4
C6-C7-C8-C4
103.6
C6-C7-C8-C4
108.7
The interaction energy (E:kcal/mol) between MM and QM in the S0 state
BAB-(CH3OH)n
E1 (B3LYP/3-21G*)
E2 [CAS(6,4)/3-21G*:MM]
E2-E1
QM1-(CH3OH)5(1)
-26.9
-27.6
-0.7
QM2-(CH3OH)5(2)
-28.8
-28.6
0.2
QM1-(CH3OH)11(1)
-33.7
-36.8
-3.1
QM2-(CH3OH)11(2)
-38.1
-35.8
2.3
QM2-(CH3OH)60(2)
-39.0
-42.5
-3.5
The interaction energy (E:kcal/mol) between MM and QM in the S0 state
E1 (MP2/cc-pVDZ)
E2 [CAS(6,4)/3-21G*:MM]
E2-E1
QM1-(CH3OH)2(1)
-16.3
-15.9
0.4
QM2-(CH3OH)2(2)
-14.6
-15.6
-1.0
E1 (MP2/cc-pVTZ)
E2 [CAS(6,4)/3-21G*:MM]
E2-E1
QM1-(CH3OH)2(1)
-15.6
-15.9
0.3
QM2-(CH3OH)2(2)
-14.4
-15.6
-1.2
The interaction energy (E:kcal/mol) between MM and QM in the S1 state
E1 [CAS(6,4)/cc-pVDZ]
E2 [CAS(6,4)/3-21G*:MM]
E2-E1
QM1-(CH3OH)2(1)
-7.89
-9.22
1.3
QM2-(CH3OH)2(2)
-7.86
-9.15
1.3
3. Coordinates of the L isomer in ground state optimized at different levels
B3LYP/6-31G*:
N
0.412396000
-1.199747000
0.490380000
N
-0.290834000
-0.893094000
-0.502414000
C
4.219553000
0.406206000
-0.227490000
C
4.115697000
-0.968817000
-0.011576000
S3
C
C
C
C
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
2.866630000
1.736495000
1.809818000
3.081970000
0.621301000
-0.637807000
-1.830019000
-3.112427000
-4.182095000
-3.980478000
-2.702569000
-1.659731000
5.190645000
5.001698000
2.755668000
3.186485000
1.041041000
0.266264000
-0.310440000
-0.999343000
-3.280567000
-5.174961000
-4.813116000
-2.517938000
-1.536845000
-0.724817000
0.681050000
1.216055000
1.621732000
1.682036000
0.783643000
1.280264000
0.414518000
-0.964969000
-1.493147000
-0.616285000
0.854978000
-1.596994000
-2.604161000
2.291190000
2.634269000
1.436087000
1.486508000
2.717380000
2.354832000
0.822164000
-1.633370000
-2.562279000
0.239412000
0.231913000
0.060026000
-0.173253000
0.323545000
-0.620796000
-0.295489000
-0.055624000
0.201084000
0.238844000
0.028278000
-0.234991000
-0.417818000
-0.038365000
0.406621000
-0.301888000
0.337234000
1.346131000
-1.648948000
-0.598112000
-0.078285000
0.370118000
0.440295000
0.067494000
MP2/6-31G*:
N
0.400172000
N
-0.274131000
C
4.189925000
C
4.094665000
C
2.856437000
C
1.728858000
C
1.790270000
C
3.053667000
C
0.593976000
C
-0.609977000
C
-1.807309000
C
-3.087539000
C
-4.156735000
C
-3.958746000
C
-2.685359000
C
-1.644766000
H
5.156563000
H
4.984205000
-1.174979000
-0.893649000
0.418192000
-0.958412000
-1.532600000
-0.717037000
0.684228000
1.227588000
1.594035000
1.666829000
0.785915000
1.292089000
0.429999000
-0.952104000
-1.488658000
-0.610691000
0.865630000
-1.581878000
0.541060000
-0.512294000
-0.258338000
-0.035663000
0.255311000
0.265061000
0.086489000
-0.178857000
0.363624000
-0.634190000
-0.317506000
-0.075360000
0.191612000
0.242610000
0.029126000
-0.242797000
-0.476640000
-0.080190000
S4
H
H
H
H
H
H
H
H
H
H
2.751761000
3.151265000
1.002680000
0.198921000
-0.248774000
-0.967630000
-3.254197000
-5.148958000
-4.794681000
-2.501228000
-2.601393000
2.303488000
2.608158000
1.342651000
1.442526000
2.704090000
2.367846000
0.839738000
-1.614390000
-2.558820000
0.424845000
-0.316440000
0.449791000
1.356544000
-1.644318000
-0.645733000
-0.108177000
0.364112000
0.454175000
0.078468000
CAS(6,4)/3-21G*:
N
0.392194000
N
-0.319813000
C
4.175337000
C
4.069008000
C
2.837669000
C
1.741429000
C
1.820840000
C
3.056919000
C
0.584312000
C
-0.578904000
C
-1.799870000
C
-3.047575000
C
-4.141617000
C
-3.996578000
C
-2.751310000
C
-1.681963000
H
5.125115000
H
4.933010000
H
2.736299000
H
3.152825000
H
0.920534000
H
0.179885000
H
-0.174068000
H
-0.926317000
H
-3.172182000
H
-5.102424000
H
-4.841360000
H
-2.620139000
-1.090182000
-1.111336000
0.462045000
-0.907833000
-1.482497000
-0.669609000
0.718189000
1.269908000
1.585571000
1.525145000
0.675425000
1.226536000
0.414579000
-0.957471000
-1.531239000
-0.712463000
0.907322000
-1.530778000
-2.543187000
2.334299000
2.613864000
1.326076000
1.167015000
2.538632000
2.290710000
0.857889000
-1.583110000
-2.593086000
0.606081000
-0.466407000
-0.260831000
-0.126824000
0.156448000
0.293087000
0.178656000
-0.102887000
0.444606000
-0.624305000
-0.256194000
-0.033896000
0.237096000
0.282156000
0.063040000
-0.194527000
-0.480489000
-0.242920000
0.260379000
-0.194431000
0.500567000
1.414744000
-1.561723000
-0.785630000
-0.076886000
0.407227000
0.489720000
0.100969000
4. Coordinates of the TS_EL transition state in the ground state optimized at
different levels
B3LYP/6-31G*:
S5
N
N
C
C
C
C
C
C
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
0.366082000
-0.503228000
4.315491000
4.085647000
2.784436000
1.725210000
1.939787000
3.255338000
0.708108000
-0.571305000
-1.756763000
-3.014117000
-4.189540000
-4.143590000
-2.911743000
-1.739553000
5.337488000
4.928070000
2.579511000
3.461872000
1.029165000
0.393505000
-0.216511000
-1.009336000
-3.082207000
-5.137539000
-5.051131000
-2.826219000
-0.696783000
-1.591680000
0.387626000
-0.983584000
-1.477370000
-0.568004000
0.828834000
1.290732000
1.723461000
1.505205000
0.587870000
1.190275000
0.462892000
-0.924270000
-1.569687000
-0.842290000
0.756964000
-1.660985000
-2.533417000
2.349838000
2.765861000
1.646333000
1.201365000
2.507118000
2.271470000
0.988385000
-1.497396000
-2.647608000
-0.102749000
-0.035308000
0.031364000
-0.148709000
-0.189051000
-0.048479000
0.129360000
0.170917000
0.327579000
-0.581678000
-0.198177000
-0.083455000
0.140201000
0.251164000
0.154245000
-0.053628000
0.056726000
-0.259720000
-0.336307000
0.306265000
0.193422000
1.376921000
-1.574686000
-0.719098000
-0.185185000
0.220740000
0.419680000
0.256857000
MP2/6-31G*:
N
0.359081000
N
-0.502143000
C
4.304338000
C
4.078614000
C
2.780087000
C
1.725470000
C
1.926712000
C
3.240848000
C
0.689935000
C
-0.561651000
C
-1.739838000
C
-2.998562000
C
-4.172657000
C
-4.132113000
-0.674633000
-1.600648000
0.396673000
-0.976361000
-1.479256000
-0.568576000
0.826866000
1.295681000
1.702407000
1.499482000
0.587725000
1.194571000
0.474031000
-0.914872000
-0.130685000
-0.037379000
0.035858000
-0.144666000
-0.197363000
-0.054126000
0.123039000
0.176940000
0.332738000
-0.602974000
-0.214062000
-0.095596000
0.149005000
0.265021000
S6
C
C
H
H
H
H
H
H
H
H
H
H
H
H
-2.903909000
-1.733665000
5.326507000
4.925570000
2.578070000
3.443054000
1.009021000
0.355428000
-0.194589000
-1.001956000
-3.063865000
-5.119503000
-5.040873000
-2.820483000
-1.565794000
-0.841423000
0.767553000
-1.649382000
-2.537097000
2.356773000
2.750578000
1.583853000
1.189595000
2.500204000
2.276933000
1.002663000
-1.481929000
-2.644462000
0.166866000
-0.070286000
0.067938000
-0.255671000
-0.347756000
0.313981000
0.239382000
1.371568000
-1.589116000
-0.746686000
-0.197046000
0.232993000
0.451208000
0.276089000
CAS(6,4)/3-21G*:
N
0.376333000
N
-0.510695000
C
4.293826000
C
4.091781000
C
2.803873000
C
1.746910000
C
1.930796000
C
3.221310000
C
0.672404000
C
-0.548360000
C
-1.754374000
C
-2.986512000
C
-4.159952000
C
-4.134290000
C
-2.922438000
C
-1.758925000
H
5.294011000
H
4.931437000
H
2.625188000
H
3.398969000
H
0.967792000
H
0.324397000
H
-0.165244000
H
-0.965749000
H
-3.034825000
H
-5.086029000
H
-5.035196000
H
-2.859510000
-0.744393000
-1.621879000
0.422148000
-0.931538000
-1.438090000
-0.566956000
0.803418000
1.291482000
1.658737000
1.458131000
0.565084000
1.196106000
0.502178000
-0.866686000
-1.529067000
-0.837724000
0.805585000
-1.586713000
-2.480681000
2.335345000
2.702284000
1.476245000
1.116109000
2.447891000
2.259204000
1.037476000
-1.412584000
-2.589957000
-0.153735000
-0.029338000
0.041817000
-0.171118000
-0.233453000
-0.086553000
0.130008000
0.196820000
0.360982000
-0.628374000
-0.225576000
-0.122285000
0.135851000
0.293370000
0.203433000
-0.042692000
0.087566000
-0.287637000
-0.399487000
0.365222000
0.313854000
1.371581000
-1.580116000
-0.798741000
-0.254428000
0.207456000
0.488748000
0.336036000
S7
5. Coordinates of the first-order saddle point
CAS(6,4)/3-21G* level
N
0.621868000
-1.718042000
N
-0.643744000
-1.711553000
C
4.115254000
0.620024000
C
4.087296000
-0.752485000
C
2.884524000
-1.414938000
C
1.692933000
-0.738453000
C
1.721216000
0.642590000
C
2.941537000
1.300105000
C
0.471346000
1.448371000
C
-0.466002000
1.306174000
C
-1.722516000
0.581966000
C
-2.936571000
1.254744000
C
-4.115205000
0.663283000
C
-4.098759000
-0.634819000
C
-2.902361000
-1.315582000
C
-1.705766000
-0.724440000
H
5.040542000
1.156849000
H
4.987904000
-1.298537000
H
2.827831000
-2.478808000
H
2.964213000
2.364465000
H
0.735399000
2.487203000
H
-0.052999000
1.121049000
H
0.054333000
0.776542000
H
-0.721053000
2.284756000
H
-2.950382000
2.261013000
H
-5.035476000
1.209932000
H
-5.003417000
-1.112637000
H
-2.854760000
-2.330690000
in the M region optimized at the
0.208667000
0.215554000
-0.084972000
-0.248420000
-0.141281000
0.101703000
0.264983000
0.171882000
0.472562000
-0.769219000
-0.380504000
-0.439577000
-0.030718000
0.444700000
0.490875000
0.096711000
-0.152544000
-0.443426000
-0.231396000
0.300040000
0.618979000
1.360667000
-1.556333000
-1.153481000
-0.809750000
-0.087137000
0.761828000
0.823223000
6. Coordinates of the E and Z isomers in the ground state optimized at the
CAS(6,4)/3-21G* level
The E isomer
N
0.367950000
-1.055142000
-0.527424000
N
-0.368011000
-1.055463000
0.527207000
C
4.215560000
0.405027000
0.186632000
C
4.088296000
-0.886525000
-0.286747000
C
2.827386000
-1.416390000
-0.507101000
C
1.717690000
-0.656278000
-0.221933000
C
1.816945000
0.654583000
0.245494000
C
3.086932000
1.169859000
0.441372000
S8
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
0.570266000
-0.570198000
-1.816901000
-3.086869000
-4.215532000
-4.088330000
-2.827443000
-1.717712000
5.188586000
4.958955000
2.706158000
3.198329000
0.906996000
0.156423000
-0.156358000
-0.906893000
-3.198225000
-5.188539000
-4.959014000
-2.706253000
1.502924000
1.502836000
0.654575000
1.169914000
0.405090000
-0.886519000
-1.416433000
-0.656340000
0.823870000
-1.476207000
-2.407698000
2.176172000
2.526407000
1.199795000
1.199523000
2.526308000
2.176248000
0.823973000
-1.476214000
-2.407803000
0.545338000
-0.545394000
-0.245413000
-0.441248000
-0.186626000
0.286616000
0.506968000
0.221884000
0.349332000
-0.491991000
-0.893378000
0.795307000
0.657727000
1.497500000
-1.497496000
-0.657973000
-0.795133000
-0.349344000
0.491722000
0.893097000
The Z isomer:
N
-0.630120000
N
0.634350000
C
-2.992910000
C
-2.980179000
C
-2.181465000
C
-1.381067000
C
-1.391491000
C
-2.210996000
C
-0.616682000
C
0.842171000
C
1.533496000
C
2.321986000
C
2.929560000
C
2.766200000
C
1.994706000
C
1.372580000
H
-3.609147000
H
-3.587352000
H
-2.170723000
H
-2.229249000
H
-1.173272000
H
-0.581527000
-0.500643000
-0.665076000
-0.171034000
-1.322002000
-1.374909000
-0.299823000
0.869347000
0.904623000
2.130567000
1.935636000
0.772272000
0.922805000
-0.172126000
-1.432504000
-1.593583000
-0.498078000
-0.109416000
-2.163169000
-2.244654000
1.796365000
2.685141000
2.745701000
1.970987000
1.948939000
-1.508696000
-0.741458000
0.380622000
0.732045000
-0.015363000
-1.140274000
0.339770000
0.848652000
0.177264000
-0.951652000
-1.540597000
-0.992738000
0.143226000
0.706134000
-2.383230000
-1.008767000
1.005553000
-1.735704000
1.089725000
-0.550656000
S9
H
H
H
H
H
H
0.839788000
1.390075000
2.462118000
3.534732000
3.243032000
1.877592000
1.783530000
2.849892000
1.901360000
-0.041009000
-2.281761000
-2.556654000
1.918977000
0.655764000
-1.368279000
-2.415273000
-1.439173000
0.596788000
7. Coordinates of the CI_E and CI_Z conical intersections optimized at
CAS(6,4)/3-21G* level
CI_E:
N
0.560223000
-1.446132000
-0.573681000
N
-0.520762000
-1.420592000
0.192476000
C
4.169913000
0.540782000
0.247961000
C
4.145320000
-0.745760000
-0.256715000
C
2.929715000
-1.351746000
-0.501637000
C
1.741812000
-0.694006000
-0.229210000
C
1.753399000
0.607520000
0.262893000
C
2.982828000
1.206805000
0.494580000
C
0.476869000
1.379980000
0.518681000
C
-0.515709000
1.357182000
-0.693008000
C
-1.787506000
0.619107000
-0.350367000
C
-3.023122000
1.241522000
-0.409373000
C
-4.177531000
0.582648000
-0.024180000
C
-4.103805000
-0.719798000
0.434856000
C
-2.880883000
-1.357350000
0.489753000
C
-1.726356000
-0.700825000
0.090943000
H
5.104704000
1.028988000
0.439162000
H
5.057663000
-1.268248000
-0.461911000
H
2.874729000
-2.342982000
-0.900925000
H
3.008186000
2.211785000
0.867996000
H
0.738836000
2.405668000
0.743740000
H
-0.019979000
0.979810000
1.393664000
H
-0.036098000
0.896887000
-1.548205000
H
-0.762418000
2.372754000
-0.973638000
H
-3.078751000
2.257079000
-0.749712000
H
-5.122591000
1.085254000
-0.075654000
H
-4.990089000
-1.237729000
0.741585000
H
-2.798405000
-2.368510000
0.828923000
CI_Z:
N
N
C
C
-0.453112642
0.507466095
-2.999584135
-3.016560699
-0.220904064
-1.153796512
-0.247881122
-1.333078620
S10
1.705030840
1.724537387
-1.476844805
-0.627567530
C
C
C
C
C
C
C
C
C
C
C
C
H
H
H
H
H
H
H
H
H
H
H
H
-2.317191769
-1.537187899
-1.509186172
-2.255591792
-0.660544062
0.784877584
1.499051318
2.245488651
2.939875713
2.954783135
2.282003393
1.516641669
-3.537314212
-3.537063390
-2.258189519
-2.228005426
-1.174738042
-0.606427241
0.757523065
1.395619563
2.248168614
3.445387971
3.465628336
2.270127065
-1.241661266
-0.130260262
0.995753006
0.900915096
2.199044934
1.884568145
0.683078271
0.910138043
-0.109416464
-1.375076866
-1.610571419
-0.620873087
-0.308518632
-2.228565260
-2.052188524
1.705776618
2.722845112
2.882605325
1.783981181
2.751133667
1.900254710
0.086667989
-2.176324598
-2.578715599
0.542999983
0.785078739
-0.053264846
-1.217803912
0.335021646
0.844298971
0.249163427
-0.886355028
-1.514973510
-0.974118870
0.205150121
0.776433555
-2.401867189
-0.897344020
1.236815472
-1.926616228
1.136409551
-0.504083964
1.916127506
0.613065826
-1.299351440
-2.439225583
-1.467715463
0.660526469
8. Full citation of Reference 31:
Gaussian 09, Revision A.1, Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.;
Scuseria, G. E.; Robb, M. A.; Cheeseman, J. R.; Scalmani, G.; Barone, V.; Mennucci,
B.; Petersson, G. A.; Nakatsuji, H.; Caricato, M.; Li, X.; Hratchian, H. P.; Izmaylov,
A. F.; Bloino, J.; Zheng, G.; Sonnenberg, J. L.; Hada, M.; Ehara, M.; Toyota, K.;
Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.; Honda, Y.; Kitao, O.; Nakai, H.;
Vreven, T.; Montgomery, Jr., J. A.; Peralta, J. E.; Ogliaro, F.; Bearpark, M.; Heyd, J.
J.; Brothers, E.; Kudin, K. N.; Staroverov, V. N.; Kobayashi, R.; Normand, J.;
Raghavachari, K.; Rendell, A.; Burant, J. C.; Iyengar, S. S.; Tomasi, J.; Cossi, M.;
Rega, N.; Millam, N. J.; Klene, M.; Knox, J. E.; Cross, J. B.; Bakken, V.; Adamo, C.;
Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.;
Pomelli, C.; Ochterski, J. W.; Martin, R. L.; Morokuma, K.; Zakrzewski, V. G.; Voth,
G. A.; Salvador, P.; Dannenberg, J. J.; Dapprich, S.; Daniels, A. D.; Farkas, Ö.;
Foresman, J. B.; Ortiz, J. V.; Cioslowski, J.; Fox, D. J. Gaussian, Inc., Wallingford
CT, 2009.
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