S1
The building blocks of cellulose: the intrinsic conformational
structures of cellobiose, its epimer, lactose, and their singly
hydrated complexes
Emilio J. Cocinero†, David P. Gamblin‡, Benjamin G. Davis*,‡ and John P. Simons*,†
†
Contribution from the Department of Chemistry, University of Oxford, Physical and Theoretical
Chemistry Laboratory, South Parks Road, Oxford OX1 3QZ, United Kingdom and
‡
the Department of Chemistry, University of Oxford, Chemical Research Laboratory, Mansfield
Road, Oxford OX1 3TA, United Kingdom
1. Synthesis of the cellulose disaccharide (1).
1.Phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
Acetyl 2,3,4,6- tetra -O- acetyl-β-D-glucopyranoside (25.0 g,
AcO
AcO
AcO
O
OPh
OAc
64.1 mmol) was dissolved in anhydrous DCM (200 mL), to
which phenol (6.6 g, 70.5 mmol) and boron trifluoride
etherate (12.1 mL, 96.2 mmol) were added. The resulting mixture was stirred under argon.
After an 18 h period, the reaction was quenched by the addition of sodium hydrogen
carbonate (500 mL, of a saturated solution). The phases were separated and the aqueous
phase was re-extracted with DCM (2 x 150 mL). The combined organics were washed with
brine (200 mL), dried (MgSO4), filtered and concentrated in vacuo. The resulting residue
was recrystallised from ethyl acetate/petrol to afford phenol 2,3,4,6-tetra-O-acetyl-β-Dglucopyranoside (17.0 g, 63%) as a white crystalline solid m.p. 147-148 ˚C {Lit. 148-149 oC};
[α]D18 -26.0 (c, 1.0 in CHCl3); δH (500 MHz, CDCl3) 2.04, 2.05, 2.07, 2.08 (12H, 4 x s, 4 x OAc),
3.86 (1H, ddd, J4,5 9.7 Hz, J5,6 2.2 Hz, J5,6’ 5.3 Hz, H-5), 4.18 (1H, dd, J5,6 2.2 Hz, J6,6’ 12.0 Hz,
H-6), 4.18 (1H, dd, J5,6’ 5.2 Hz, J6,6’ 12.2 Hz, H-6’), 5.08 (1H, d, J1,2 7.5 Hz, H-1), 5.17 (1H, at, J
9.5 Hz, H-4), 5.26-5.33 (2H, m, H-3, H-4), 6.98-7.00 (1H, m, ArH), 7.06-7.09 (2H, m, ArH),
7.29-7.32 (2H, m, ArH).
S2
Phenyl β-D-glucopyranoside
HO
O
HO
HO
OPh
Phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranoside
OH
(16.8 g, 39.6 mmol) and sodium methoxide (220 mg, 3.96 mmol) were added to a stirred
solution of methanol (150 mL). After 30 min, t.l.c. (ethyl acetate/petrol, 1:1) indicated the
formation of a product (Rf 0) with complete consumption of the starting material (Rf 0.5).
The reaction was neutralised by the addition of Dowex-50 ion exchange resin® after which
point the reaction was filtered and concentrated in vacuo. The resulting residue was
recrysatllised from hot ethyl acetate to afford phenyl β-D-glucopyranoside (9.7 g, 96%) as a
white crystalline solid m.p. oC; [α]D18 -62.0 (c, 1.0 in CH3OH); δH (500 MHz, CD3OD) 3.39-3.49
(4H, m, H-2, H-3, H-4, H-5), 3.72 (1H, dd, J5,6 5.3 Hz, J6,6’ 12.1 Hz, H-6), 3.91 (1H, dd, J5,6’
2.2 Hz, J6,6’ 12.1 Hz, H-6’), 4.91 (1H, d, J1,2 10.1 Hz, H-1), 6.99-7.03 (1H, m, ArH), 7.09-7.12
(2H, m, ArH), 7.28-7.32 (2H, m, ArH).
Phenyl 4,6-O-benzylidene-β-D-glucopyranoside
Phenyl β-D-glucopyranoside (9.6g, 37.5 mmol)
Ph
O
O
O
HO
OPh
OH
was dissolved in anhydrous N,N-dimethyl formamide
(100 mL) and benzaldehyde dimethyl acetal (8.4 mL,
56.3 mmol) and para toluene sulfonic acid (700 mg, 3.75 mmol) were added. The resulting
solution was placed on a rotatory evaporator at 240 mbar at 60 oC. After 4 h, t.l.c.
(petrol:ethyl acetate, 1:3) showed the formation of a product (Rf 0.4) with complete
consumption of the starting material (Rf 0). The reaction was cooled to RT and quenched
by the addition of triethylamine (5 mL). The solution was partitioned between DCM
(200 mL) and water (200 mL) and the phases were separated. The aqueous phase was
re-extracted with DCM (2 x 100 mL). The combined organic layers were washed with brine
S3
(3 x 200 mL), dried (MgSO4), filtered and concentrated in vacuo. The resulting residue was
recrystallised from ethyl acetate/petrol to afford phenyl 4,6-O-benzylidene-β-Dglucopyranoside (10.6 g, 82%) as a white crystalline solid; [α]D18 -54.3 (c, 1.4 in CH3Cl); δH
(500 MHz, CD3Cl) 3.60 (1H, dat, J5,6 5.2 Hz, J 9.7 Hz, H-5), 3.66 (1H, at, J 9.2 Hz, H-4), 3.853.99 (2H, m, H-2, H-6), 3.93 (1H, at, J 9.2 Hz, H-3), 4.39 (1H, dd, J5,6’ 4.6 Hz, J6,6’ 10.3 Hz,
H-6’), 5.04 (1H, d, J1,2 8.0 Hz, H-1), 5.56 (1H, s, PhCH), 7.06-7.53 (10H, m, ArH).
Phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
Ph
Phenyl 4,6 -O- benzylidene-β-D-glucopyranoside (4.5 g,
O
O
O
BnO
OPh
OBn
13.0 mmol)
was
suspended
in
anhydrous
dimethylformamide (100 mL) to which benzyl bromide
(5.2 mL, 43.3 mmol) was added. The mixture was cooled to 0 oC and sodium hydride (60%
in mineral oil, 1.7 g, 43.3 mmol) was added portionwise over a period of 10 mins. After
18 h, t.l.c. (petrol:ethyl acetate, 2:1) showed the formation of a single product (Rf 0.8). The
reaction was quenched by the careful addition of methanol (ca 50 mL). The reaction was
partitioned between diethyl ether (100 mL) and water (100 mL) and the phases separated.
The aqueous phase was re-extracted with diethyl ether (2 x 100 mL). The combined
organic layers were washed with brine (250 mL), dried (MgSO4), filtered and concentrated
in vacuo. The resulting residue was recrystallised from ethyl acetate/petrol to afford
phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside (5.2 g, 76%) as a white
crystalline solid m.p. 127-128 ˚C; [α]D18 -40.0 (c, 1.2 in CH3Cl); δH (500 MHz, CD3Cl) 3.58 (1H,
dat, J5,6’ 5.0 Hz, J 9.9 Hz, H-5), 3.76-3.89 (4H, m, H-2, H-3, H-4, H-6), 4.41 (1H, dd, J5,6’ 5.0 Hz,
J6,6’ 10.6 Hz, H-6’), 4.85, 4.97 (2H, ABq, J 11.4 Hz, PhCH2), 4.88, 5.00 (2H, ABq, J 11.0 Hz,
PhCH2), 5.16 (1H, d, J1,2 7.6 Hz, H-1), 5.62 (1H, s, PhCH), 7.07-7.53 (20H, m, ArH).
Phenyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside
S4
Phenyl 2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranoside
BnO
O
HO
BnO
OPh
OBn
(4.9 g, 9.31 mmol) was dissolved in anhydrous THF (50 mL) and
the resulting solution was cooled to 0 oC, to which methyl
orange (speck) and sodium cyanoborohydride (11.7 g, 186.3 mmol) was added. The
resulting solution was acidified by the slow addition of hydrochloric acid in dioxane (4M) to
keep the indicator intensely pink. The resulting mixture was stirred under argon at RT.
After a 12 h period, t.l.c. (petrol:ethyl acetate, 1:1) indicated the formation of a product (Rf
0.4) with complete consumption of the starting material (Rf 0.6). The reaction was diluted
with ice water (500 mL) and filtered through celite®. The filtrate was extracted with DCM
(3 x 100 mL) and the combined organics were stirred in aqueous hydrochloric acid (2M,
300 mL) overnight. The organic layer was then washed with sodium hydrogen carbonate
(600 mL, of a saturated aqueous solution), dried (MgSO4) and concentrated in vacuo. The
resulting residue was purified by flash column chromatography (petrol:ethyl acetate, 1:1)
to afford phenyl 2,3,6-tri-O-benzyl-β-D-glucopyranoside (4.2 g, 86%) as a white amorphous
foam; IR 3442 OH; [α]D18 -43.0 (c, 1.1 in CH3Cl); δH (500 MHz, CD3Cl) 2.64 (1H, d, J 2.0 Hz,
OH-4), 3.59 (1H, at, J 9.0 Hz, H-3), 3.61-3.65 (1H, m, H-5), 3.72-3.79 (3H, m, H-2, H-4, H-6),
3.86 (1H, dd, J5,6’ 3.3 Hz, J6,6’ 10.3 Hz, H-6’), 4.58, 4.63 (2H, ABq, J 12.0 Hz, PhCH2), 4.79, 5.01
(2H, ABq, J 11.3 Hz, PhCH2), 4.86, 5.09 (2H, ABq, J 11.0 Hz, PhCH2), 5.07 (1H, s, H-1), 7.097.40 (20H, m, 20 x ArH); δC (125 MHz, CD3Cl) 70.0 (t, C-6), 71.2 (d, C-4), 73.6 (t, PhCH2), 74.3
(d, C-5), 75.0, 75.4 (2 x t, 2 x PhCH2), 81.5 (d, C-2), 84.0 (d, C-3), 101.6 (d, C-1), 116.8, 122.6,
127.7, 127.8, 127.9, 128.0, 128.3, 128.4, 128.5, 128.6, 129.6 (11 x d, 20 x ArC), 137.9,
138.1, 138.5, 157.3 (4 x s, 4 x ArC); m/z (ES+) 585 (100%, M+MeCN/NH4+). HRMS found
549.2252. calcd 549.2248 for C33H34O6Na.
2,3,6-tri-O-benzyl-1-deoxy-D-glucopyranoside
S5
0.3g (7%) of 2,3,6-tri-O-benzyl-1-deoxy-D-glucopyranoside
BnO
O
HO
BnO
was also extracted from the above procedure (Rf 0.45); [α]D20 OBn
52.2 (c, 0.6 in H2O); δH (500 MHz, CD3Cl) 2.50 (1H, bs, OH), 3.26
(1H, at, J 9.6 Hz, H-1), 3.37-3.41 (1H, m, H-5), 3.47 (1H, at, J 8.9 Hz, H-3), 3.57 (1H, at, J
9.2 Hz, H-4), 3.63-3.67 (2H, m, H-2, H-6), 3.72 (1H, dd, J5,6’ 3.2 Hz, J6,6’ 10.4 Hz, H-6’), 4.07
(1H, dd, J1,1’ 11.4 Hz, J1’,2 5.6 Hz, H-1’), 4.56, 4.61 (2H, ABq, J 12.6 Hz, PhCH2), 4.65, 4.69 (2H,
ABq, J 11.9 Hz, PhCH2), 4.79, 5.03 (2H, ABq, J 11.5 Hz, PhCH2), 7.33-7.39 (15H, m, ArH); δC
(125 MHz, CD3Cl) 68.1 (t, C-1), 69.9 (t, C-6), 70.8 (d, C-4), 73.1, 73.7, 75.2 (3 x t, 3 x PhCH2),
78.1 (d, C-2), 78.8 (d, C-5), 85.4 (d, C-3), 127.6, 127.7, 127.8, 127.9, 128.0, 128.3, 128.4,
128.5, 128.6 (9 x d, 15 x ArC), 137.8, 138.0, 138.6 (3 x s, 3 x ArC);
Phenyl
2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→4)-2,4,6-tri-O-benzyl-β-D-
glucopyranoside
Phenyl
AcO
O
AcO
AcO
2,3,6-tri-O-benzyl-β-D-
BnO
O
O
BnO
OPh
OAc
OBn
glucopyranoside (840 mg, 1.58 mmol) in
anhydrous
DCM
(10 mL)
and
benzyl
2,3,4,6-tetra-O-acetyl-1-thio-β-D-glucopyranoside (600 mg, 1.32 mmol) in DCM (10 mL)
were added to a dried flask containing activated 4Å molecular sieves (ca 100 mg) via
cannula. The resulting solution was stirred for 1 h, after which point methyl
trifluromethanesulfonate (750 µL, 6.6 mmol) was added. After a 20 h period, t.l.c.
(petrol:ethyl acetate, 3:1) indicated the formation of a major product (Rf 0.2) with
complete consumption of the starting material (Rf 0.25). The reaction was quenched with
triethylamine (ca 1 mL) and the solution was filtered through celite® and concentrated in
vacuo. The resulting residue was purified by flash column chromatography (petrol:ethyl
acetate, 3:2) to afford phenyl 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl-(1→4)-2,4,6-tri-Obenzyl-β-D- glucopyranoside (960 mg, 85%) as a white amorphous foam; IR 1757 C=O;
S6
[α]D18 -31.0 (c, 1.0 in CH3Cl); δH (500 MHz, CD3Cl) 1.96, 1.98, 1.99, 2.01 (12H, 4 x s, 4 x OAc),
3.33-3.36 (1H, m, H-5b), 3.51 (1H, ddd, J4,5 9.7 Hz, J5,6 2.3 Hz, J5,6’ 3.5 Hz, H-5a), 3.67 (1H, at,
J 8.5 Hz, H-3a), 3.69 (1H, at, J 7.4 Hz, H-2a), 3.75-3.80 (2H, m, H-6ª, H-6’a), 3.90 (1H, dd, J5,6
2.2 Hz, J6,6’ 12.7 z, H-6’b), 4.02 (1H, dd, J3,4 8.7 Hz, J4,5 9.5 Hz, H-4a), 4.15 (1H, dd, J5,6’ 4.0 Hz,
J6,6’ 12.4 Hz, H-6’b), 4.49, 4.73 (2H, ABq, J 12.0 Hz, PhCH2), 4.68 (1H, d, J1,2 8.1 Hz, H-1b),
4.75-4.79 (2H, m, 2 x PhCHH), 4.95-5.06 (6H, m, H-1a, H-2b, H-3b, H-4b, 2 x PhCHH), 7.057.37 (20H, m, ArH); δC (125 MHz, CD3Cl) 20.6, 20.7, 20.8 (3 x q, 4 x OAc), 61.6 (t, C-6b), 67.7
(t, C-6a), 68.0 (d, C-4b), 71.6 (d, C-5b), 71.9, 73.1 (2 x d, C-2b, C-3b), 73.6 (t, PhCH2), 74.8
(d, C-5a), 75.0, 75.1 (2 x t, 2 x PhCH2), 77.0 (d, C-4a), 81.4 (d, C-2a), 82.6 (d, C-3a), 100.1 (d,
C-1b), 101.6 (d, C-1a), 116.9, 122.7, 127.3, 127.4, 127.6, 127.9, 128.1, 128.2, 128.3, 128.5,
129.5 (11 x d, 20 x ArC), 137.8, 138.1, 138.9 (3 x s, 3 x ArC), 157.3 (s, ArC), 169.1, 169.3,
170.2, 170.6 (4 x s, 4 x CO); m/z (ES+) 915 (100%, M+MeCN/NH4+). HRMS found 879.3200.
calcd 879.3198 for C47H52O15Na.
Phenyl β-D-glucopyranosyl-(1→4)-β-D- glucopyranoside
Phenyl
2,3,4,6-tetra-O-acetyl-β-D-
glucopyranosyl-(1→4)-2,4,6-tri-O-
HO
O
HO
HO
O
HO
O
HO
OPh
OH
OH
benzyl-β-D-
glucopyranoside
(700 mg, 0.82 mmol) and sodium
methoxide (10 mg, 0.16 mmol) were added to a stirred solution of methanol (10 mL). After
90 min, t.l.c. (ethyl acetate/methanol, 9:1) indicated the formation of a single product (Rf
0.4) with complete consumption of the starting material (Rf 0.9). The reaction was
neutralised with by the addition of Dowex-50 ion exchange resin®, after which point the
reaction was filtered and concentrated in vacuo. The crude residue was purified via flash
column chromatography (methanol/ethyl acetate, 5:95) to afford the partially protected
disaccharide. This intermediate was immediately resuspended in absolute methanol
S7
(20 mL) and palladium on carbon (moist 10%) was added. The resulting suspension was
degassed and purged with hydrogen gas, then left to stir under an atmosphere of
hydrogen. After an 18 h period, t.l.c. (ethyl acetate) indicated the formation of a single
product (Rf 0.0). The solution was filtered through celite® and concentrated in vacuo to
afford phenyl β-D-glucopyranosyl-(1→4)-β-D- glucopyranoside (315 mg, 98%) as a white
amorphous solid; [α]D20 -52.2 (c, 0.6 in H2O) {Lit.,Error! Bookmark not defined. [α]D20 -59.5 (c, 1.0 in
H2O); Lit.,Error! Bookmark not defined. [α]D18 -53.1 (H2O)}}; δH (500 MHz, D2O) 3.28 (1H, at, J 9.2 Hz,
H-2b), 3.37 (1H, at, J 9.4 Hz, H-4b), 3.43-3.48 (2H, m, H-3b, H-5b), 3.54-3.58 (1H, m, H-2a),
3.67-3.71 (4H, m, H-3a, H-4a, H-5a, H-6b), 3.78 (1H, dd, J5,6 2.9 Hz, J6,6’ 12.2 Hz, H-6a), 3.88
(1H, dd, J5,6’ 1.8 Hz, J6,6’ 12.3 Hz, H-6’b), 3.93 (1H, d, J6,6’ 12.1 Hz, H-6’a), 4.48 (1H, d, J1,2
7.8 Hz, H-1b), 5.10 (1H, d, J1,2 7.9 Hz, H-1a), 7.08-7.11 (3H, m, ArH), 7.33-7.37 (2H, m, ArH);
δC (125 MHz, D2O) 59.9 (t, C-6a), 60.6 (t, C-6b), 69.5 (d, C-4b), 72.8 (d, C-2a), 73.2, 74.9,
78.4 (3 x d, C-3a, C-4a, C-5a), 74.2 (d, C-2b), 75.6, 76.0 (2 x d, C-3b, C-5b), 100.0 (d, C-1a),
102.6 (d, C-1b), 116.6, 123.4, 129.9 (3 x d, 5 x ArC), 156.5 (s, ArC); m/z (ES-) 417 (100%, MH+). HRMS found 441.1364. calcd 441.1367 for C18H26O11Na.
S8
2. Cartesian Coordinates of the cellulose dissacharide (1) and the mono-hydrates of(1) and
its C-4’ epimer (2).
β-D-phenyl cellobioside
Conformer 1
B3LYP/6-311+G*
Total energy: -1529.3816439 H
ZPE: 0.451774 H
MP2/6-311++G** // B3LYP/6-311+G*
Total energy: -1525.4325267 H
Cartesian coordinates:
C
0.000000
0.000000
0.000000
C
0.000000
0.000000
1.394090
C
1.202335
0.000000
2.102319
C
2.409176
-0.011802
1.411831
C
2.424642
-0.028883
0.016381
C
1.219443
-0.022433
-0.679623
O
-1.148775
0.015917
2.167205
C
-2.369148
-0.368100
1.605585
O
-2.912840
0.721089
0.880163
C
-4.194479
0.453121
0.284664
C
-5.234926
0.081523
1.364498
C
-4.688930
-1.053686
2.229458
C
-3.300799
-0.721342
2.761458
O
-6.419329
-0.375968
0.708107
C
-7.626861
0.313773
0.929362
O
-7.460308
1.642116
0.470281
C
-8.601791
2.510405
0.557937
C
-9.180579
2.527253
1.976783
C
-9.394672
1.107744
2.483477
C
-8.099807
0.313355
2.391066
C
-8.111197
3.883232
0.098683
O
-7.045821
4.376853
0.885170
O
-10.410146
3.240908
1.916383
O
-8.353762
-0.996077
2.867927
O
-9.862433
1.194424
3.825228
C
-4.540693
1.703931
-0.512693
O
-4.593995
2.871470
0.300845
O
-5.578495
-1.304778
3.318538
O
-2.862026
-1.867635
3.480721
H
-6.248936
3.847536
0.714821
H
-7.824590
3.816458
-0.959738
H
-8.933746
4.594572
0.184478
H
-9.384772
2.160100
-0.131423
H
-8.476645
3.040660
2.642782
H
-10.809960
3.211064
2.795023
H
-8.354664
-0.226134
0.310969
H
-7.346896
0.803369
3.019587
H
-10.159598
0.617118
1.862541
H
-9.888838
0.297478
4.184407
H
-7.490825
-1.395670
3.067934
H
-5.435577
0.962397
1.977028
H
-3.797871
1.830428
-1.308838
H
-5.525902
1.595027
-0.958504
H
-3.727888
3.016404
0.701929
H
-4.108682
-0.391346
-0.415712
H
-5.138448
-1.926203
3.915012
S9
H
H
H
H
H
H
H
H
H
-4.620989
-3.357772
-2.024263
-2.224974
1.175524
3.341248
3.366766
1.218251
-0.928803
-1.958115
0.151185
-1.665190
-1.232325
0.010107
-0.012241
-0.041176
-0.022700
0.048592
1.609049
3.424551
3.915121
0.939861
3.186471
1.967463
-0.520680
-1.764832
-0.553028
Conformer 2
B3LYP/6-311+G*
Total energy: -1529.3783377 H
ZPE: 0.451333 H
MP2/6-311++G** // B3LYP/6-311+G*
Total energy: -1525.4293022 H
Cartesian coordinates:
C
0.000000
0.000000
0.000000
C
0.000000
0.000000
1.395470
C
1.201347
0.000000
2.102835
C
2.405697
0.022413
1.396871
C
2.417673
0.028720
0.005167
C
1.207378
0.011728
-0.689585
O
-1.249046
-0.016297
1.992743
C
-1.386031
0.371302
3.328390
O
-1.032731
-0.714125
4.169501
C
-1.196668
-0.436532
5.570364
C
-2.673853
-0.116932
5.883346
C
-3.119867
1.047983
5.002740
C
-2.856944
0.732315
3.535499
O
-2.759569
0.265913
7.254981
C
-3.625774
-0.460328
8.093220
O
-3.343294
-1.836810
7.948800
C
-4.010311
-2.707273
8.873291
C
-5.531170
-2.501657
8.808560
C
-5.895973
-1.022107
8.871022
C
-5.119736
-0.238407
7.820271
C
-3.612601
-4.130828
8.477855
O
-2.215197
-4.314567
8.399471
O
-6.112653
-3.226846
9.883398
O
-5.503467
1.121656
7.909446
O
-7.303334
-0.926779
8.677049
C
-0.627795
-1.634127
6.319937
O
-1.267573
-2.861695
5.993598
O
-4.506507
1.317883
5.210716
O
-3.235444
1.888915
2.798534
H
-1.890327
-3.865714
7.602263
H
-3.993801
-4.822785
9.229888
H
-4.092152
-4.374898
7.519148
H
-3.656591
-2.489170
9.890221
H
-5.902977
-2.892261
7.849633
H
-7.059050
-3.032188
9.892273
H
-3.374660
-0.107761
9.101756
H
-5.361843
-0.630981
6.825350
H
-5.638848
-0.630853
9.866802
H
-7.525659
0.010668
8.599312
H
-5.217298
1.543002
7.083192
H
-3.279010
-1.003370
5.686270
H
0.447042
-1.697379
6.112957
H
-0.767674
-1.490287
7.389379
H
-1.103248
-3.071235
5.066139
S10
H
H
H
H
H
H
H
H
H
H
H
-0.592370
-4.784600
-2.539203
-3.460340
-3.175154
-0.740668
1.206462
3.340176
3.358544
1.201461
-0.947782
0.442162
1.942072
1.938277
-0.132239
1.695020
1.237236
-0.048423
0.022588
0.040783
0.012135
-0.009901
5.845127
4.525956
5.282510
3.231027
1.854954
3.539553
3.183839
1.948623
-0.534090
-1.774699
-0.527124
Conformer 3
B3LYP/6-311+G*
Total energy: -1529.3752466 H
ZPE: 0.451874 H
MP2/6-311++G** // B3LYP/6-311+G*
Total energy: -1525.4290976 H
Cartesian coordinates:
C
0.000000
0.000000
0.000000
C
0.000000
0.000000
1.396220
C
1.205937
0.000000
2.100066
C
2.413401
0.011764
1.406280
C
2.424128
0.031149
0.012016
C
1.216221
0.025326
-0.682478
O
-1.147143
-0.064675
2.171990
C
-2.295569
0.677349
1.861505
O
-2.980695
0.079084
0.770847
C
-4.273875
0.653571
0.521360
C
-4.137887
2.148143
0.154689
C
-3.344190
2.860699
1.249491
C
-2.025113
2.151196
1.536154
O
-5.444133
2.725091
0.095349
C
-5.875460
3.303617
-1.113461
O
-5.905279
2.286370
-2.097570
C
-6.380427
2.659232
-3.400839
C
-5.607153
3.864015
-3.947375
C
-5.576647
4.986308
-2.919366
C
-5.016233
4.481494
-1.596875
C
-6.231685
1.410092
-4.268901
O
-4.900803
0.937219
-4.325812
O
-6.266251
4.278178
-5.138481
O
-5.026977
5.561164
-0.680149
O
-4.785136
6.041481
-3.455077
C
-4.921905
-0.204719
-0.556338
O
-4.153687
-0.258897
-1.756474
O
-3.089025
4.213197
0.866280
O
-1.433292
2.847674
2.629890
H
-4.653269
0.578340
-3.457493
H
-6.910785
0.635456
-3.887532
H
-6.532553
1.655180
-5.288308
H
-7.445584
2.929238
-3.341268
H
-4.578279
3.556785
-4.171026
H
-5.823020
5.074947
-5.457123
H
-6.888471
3.659394
-0.888036
H
-3.987750
4.140008
-1.764499
H
-6.602865
5.348945
-2.755583
H
-4.678270
6.707325
-2.762640
H
-4.427347
5.321724
0.046255
H
-3.625128
2.228516
-0.805708
H
-5.074241
-1.214114
-0.159050
S11
H
H
H
H
H
H
H
H
H
H
H
H
H
-5.885186
-3.350548
-4.890083
-2.486392
-3.949794
-1.384490
-0.511038
-2.907981
1.179457
3.347115
3.364693
1.213533
-0.936307
0.219101
-0.767308
0.577615
4.588991
2.859143
2.219785
2.579498
0.604465
-0.025798
0.006750
0.044685
0.030434
-0.026642
-0.828271
-1.594770
1.430262
1.523031
2.166479
0.650821
2.725084
2.768182
3.184246
1.959184
-0.527861
-1.767643
-0.540512
Conformer 4
B3LYP/6-311+G*
Total energy: -1529.378202 H
ZPE: 0.451685 H
MP2/6-311++G** // B3LYP/6-311+G*
Total energy: -1525.4287957 H
Cartesian coordinates:
C
0.000000
0.000000
0.000000
C
0.000000
0.000000
1.534550
O
1.331985
0.000000
2.018011
C
2.198979
-1.048745
1.570483
C
2.238509
-1.083618
0.033967
C
0.819279
-1.174496
-0.510308
O
-0.668435
1.082378
2.111330
C
-0.190409
2.414946
1.847816
C
0.217916
3.078671
3.174453
O
0.516391
4.461007
2.947042
C
-0.562153
5.244978
2.433678
C
-1.011949
4.687153
1.087691
C
-1.337978
3.199400
1.211848
O
-0.093639
6.539941
2.237247
C
-0.069728
7.425177
3.294187
C
-0.040035
7.042190
4.635547
C
-0.013142
8.026093
5.625806
C
0.001444
9.376595
5.289470
C
-0.013422
9.745925
3.943138
C
-0.052461
8.777423
2.946701
C
1.468895
2.496282
3.820624
O
2.627766
2.650663
3.001602
O
-1.655393
2.763494
-0.101688
O
-2.150779
5.410247
0.658991
C
3.555535
-0.750751
2.207578
O
4.109029
0.470414
1.766486
O
2.936134
-2.233381
-0.453807
O
0.773102
-1.121081
-1.931215
O
-1.354460
-0.064299
-0.441790
H
3.608483
1.210863
2.154541
H
3.437913
-0.767974
3.298652
H
4.262752
-1.542167
1.945052
H
1.833725
-2.020915
1.936342
H
2.713916
-0.169218
-0.333699
H
3.875719
-2.032608
-0.527526
H
-0.543912
-0.882131
1.894902
H
0.459904
0.923267
-0.371108
H
0.366900
-2.116836
-0.165665
H
1.330454
-1.831016
-2.275997
H
-1.341692
-0.276958
-1.385758
S12
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
0.675448
1.627241
1.343560
2.752891
-0.615560
-1.858100
-2.219537
-0.182579
-2.502486
-1.395413
-0.078810
-0.002983
0.027507
0.008671
-0.008715
2.395789
2.986887
1.428315
3.591136
2.982574
1.811388
3.089279
4.814548
4.954801
5.242018
9.046259
10.795300
10.134074
7.725299
5.995370
1.184056
4.787754
3.979503
2.819703
3.887363
-0.108619
1.861449
0.378657
-0.117921
3.151074
1.896753
3.666252
6.065490
6.668581
4.908763
S13
β-D-phenyl cellobioside·H2O
Conformer 1
B3LYP/6-311+G*
Total energy: -1605.8464964 H
ZPE: 0.477939 H
MP2/6-311++G** // B3LYP/6-311+G*
Total energy: -1601.7277401 H
Cartesian coordinates:
C
-5.115485
-0.919172
-0.653392
C
-4.948891
-0.263201
0.566789
C
-5.999683
-0.204279
1.484501
C
-7.219261
-0.795931
1.176698
C
-7.403730
-1.443227
-0.046651
C
-6.349675
-1.498930
-0.953676
O
-3.776706
0.341586
0.968173
C
-2.822304
0.696102
0.020341
O
-2.037669
-0.464026
-0.263463
C
-0.965954
-0.271826
-1.194452
C
0.014916
0.773991
-0.637598
C
-0.742112
2.058125
-0.298435
C
-1.939026
1.788760
0.613038
O
0.992694
1.098009
-1.641860
C
2.340254
0.839696
-1.369345
O
2.481151
-0.559534
-1.182736
C
3.789408
-1.054496
-0.865471
C
4.323611
-0.343916
0.390207
C
4.317689
1.158704
0.132296
C
2.894089
1.605199
-0.159550
C
3.635094
-2.563356
-0.719115
O
2.811191
-2.941044
0.379490
O
5.646385
-0.733306
0.717477
O
2.809456
2.999559
-0.452436
O
4.765558
1.901401
1.257488
C
-0.369382
-1.656617
-1.411926
O
0.083419
-2.250810
-0.192774
O
0.053855
3.014745
0.384437
O
-2.717973
2.960151
0.769287
H
1.885017
-2.676534
0.216412
H
3.234749
-2.972696
-1.653222
H
4.614907
-3.010915
-0.547470
H
4.476851
-0.860823
-1.703557
H
3.655021
-0.557722
1.230803
H
5.582483
-1.463807
1.362211
H
2.870110
1.163763
-2.273416
H
2.288811
1.387998
0.727891
H
4.964102
1.378806
-0.731356
H
5.593731
1.501036
1.557090
H
3.344349
3.466037
0.205284
H
0.491913
0.364782
0.254179
H
-1.125064
-2.298735
-1.877829
H
0.497081
-1.591366
-2.064448
H
-0.657490
-2.279154
0.426726
H
-1.358647
0.089757
-2.157187
H
0.859440
3.220412
-0.122085
H
-1.111867
2.488428
-1.241644
H
-1.574426
1.433358
1.586475
H
-2.113559
3.674672
1.012054
H
-3.306432
1.049887
-0.901137
H
-5.843110
0.314729
2.423376
H
-8.032759
-0.743723
1.893231
S14
H
H
H
O
H
H
-8.357600
-6.476776
-4.292024
4.688381
3.883161
4.972735
-1.900680
-2.007838
-1.005159
-2.753299
-2.991601
-3.514118
-0.286457
-1.904030
-1.350571
2.351673
1.849278
2.865790
Conformer 2
B3LYP/6-311+G*
Total energy: -1605.8406706 H
ZPE: 0.477137 H
MP2/6-311++G** // B3LYP/6-311+G*
Total energy: -1601.7263627 H
Cartesian coordinates:
C
3.879883
-1.504804
-0.421891
C
2.563352
0.333851
-1.366084
C
3.142352
1.296074
-0.318367
C
4.573341
0.876760
-0.021683
C
4.576444
-0.534396
0.541971
H
4.562218
-1.673753
-1.268148
H
2.556238
1.226647
0.603577
H
5.161023
0.899162
-0.952631
H
4.047489
-0.515109
1.501202
O
1.228366
0.598114
-1.716982
H
3.112729
0.445451
-2.309124
O
3.166215
2.633154
-0.790566
H
2.264617
2.979045
-0.681587
O
5.187051
1.727970
0.940056
H
5.014073
2.639995
0.669218
O
5.901475
-1.023404
0.725659
H
6.381903
-0.371962
1.252955
O
2.625556
-1.006030
-0.900325
C
3.557257
-2.852302
0.229324
H
3.296494
-3.578274
-0.548899
H
4.441845
-3.215909
0.753328
O
2.498529
-2.759782
1.177026
H
1.648171
-2.731188
0.696537
C
-0.829188
-0.522621
-1.181325
C
0.226826
0.496548
-0.698001
C
-0.452437
1.855652
-0.531936
C
-1.655024
1.735207
0.395483
C
-2.622817
0.682601
-0.138473
H
-1.167313
-0.215875
-2.182914
H
0.648878
0.167384
0.252900
H
-0.797024
2.197967
-1.518415
H
-1.319712
1.416180
1.389538
H
-3.044832
0.996193
-1.105168
O
-1.952421
-0.557629
-0.282095
O
0.468208
2.813454
-0.009637
H
-0.041454
3.597328
0.237942
O
-2.251741
3.027049
0.455334
H
-2.949356
3.019422
1.121978
O
-3.642163
0.546704
0.808915
C
-7.382843
-1.043213
-0.125344
C
-6.308364
-1.307366
-0.969651
C
-5.037376
-0.800838
-0.691889
C
-4.854614
-0.009112
0.441202
C
-5.923638
0.256822
1.298170
C
-7.181707
-0.262420
1.013866
H
-8.365277
-1.445563
-0.347170
H
-6.448804
-1.924238
-1.851425
S15
H
H
H
C
H
H
O
H
O
H
H
-4.201688
-5.753813
-8.009154
-0.345244
-1.122894
0.565369
-0.036382
-0.760580
1.458087
1.579873
1.937524
-1.048737
0.868169
-0.051795
-1.963607
-2.562773
-2.010556
-2.524510
-2.333047
-0.429988
-0.284240
-1.247769
-1.332965
2.177742
1.683602
-1.274489
-1.762697
-1.866965
-0.001250
0.609434
2.373655
3.317312
2.137255
Conformer 3
B3LYP/6-311+G*
Total energy: -1605.8416636 H
ZPE: 0.477164 H
MP2/6-311++G** // B3LYP/6-311+G*
Total energy: -1601.7250946 H
Cartesian coordinates:
C
4.184937
-1.504122
-0.286383
C
2.756005
0.191338
-1.289221
C
3.300153
1.262180
-0.331090
C
4.744266
0.923816
0.009254
C
4.829097
-0.461561
0.633617
H
4.829900
-1.631095
-1.168909
H
2.714688
1.254619
0.595691
H
5.341517
0.937143
-0.915187
H
4.297085
-0.453589
1.592699
O
1.412253
0.374553
-1.663270
H
3.303766
0.239531
-2.238589
O
3.277698
2.555197
-0.908285
H
2.359945
2.871844
-0.854964
O
5.294800
1.851972
0.938064
H
5.128190
2.740332
0.595280
O
6.183206
-0.855380
0.826418
H
6.614895
-0.171276
1.354082
O
2.873397
-1.093122
-0.703455
C
3.993859
-2.860959
0.391316
H
3.651303
-3.583408
-0.362063
H
4.957369
-3.199576
0.774657
O
3.101991
-2.806353
1.486629
H
2.201560
-2.645054
1.158320
C
-0.592761
-0.771047
-0.966776
C
0.408666
0.358010
-0.644119
C
-0.326421
1.695139
-0.655992
C
-1.561012
1.676336
0.244295
C
-2.458889
0.507290
-0.164074
H
-0.927052
-0.651655
-2.007953
H
0.846167
0.170164
0.338109
H
-0.651830
1.898333
-1.686181
H
-1.249419
1.511930
1.284658
H
-2.840447
0.647072
-1.185463
O
-1.725396
-0.702674
-0.083657
O
0.546676
2.742723
-0.234791
H
-0.006693
3.526797
-0.104525
O
-2.176344
2.941090
0.096040
H
-2.764115
3.103151
0.859017
O
-3.541827
0.411244
0.733441
C
-6.912767
-1.716880
-0.504311
C
-5.966079
-2.324052
0.320079
C
-4.828259
-1.624113
0.718908
S16
C
C
C
H
H
H
H
H
C
H
H
O
H
O
H
H
-4.652699
-5.592518
-6.724468
-7.796580
-6.110521
-4.079892
-5.440967
-7.462821
-0.029109
-0.777926
0.872232
0.346096
-0.427654
-3.870236
-3.830144
-3.963058
-0.313760
0.308568
-0.401647
-2.265267
-3.346485
-2.079400
1.338611
0.078259
-2.175800
-2.898234
-2.282305
-2.460545
-2.359343
2.775281
2.943223
1.821363
0.287278
-0.529890
-0.927305
-0.812534
0.653330
1.356678
-0.834953
-1.561108
-0.803305
-1.147785
-1.401466
0.542048
1.110079
2.256024
3.202670
2.111088
Conformer 4
B3LYP/6-311+G*
Total energy: -1605.8419277 H
ZPE: 0.476884 H
MP2/6-311++G** // B3LYP/6-311+G*
Total energy: -1601.724278 H
Cartesian coordinates:
C
-4.109420
-1.379533
0.594472
C
-2.686090
0.490152
1.207813
C
-3.287085
1.362849
0.095495
C
-4.734985
0.944781
-0.118671
C
-4.815785
-0.533829
-0.470441
H
-4.711154
-1.352006
1.515627
H
-2.736798
1.199181
-0.838889
H
-5.296486
1.122573
0.811101
H
-4.326456
-0.698676
-1.437733
O
-1.336127
0.762962
1.503500
H
-3.204444
0.699907
2.152232
O
-3.277656
2.739331
0.432957
H
-2.367780
3.056205
0.305602
O
-5.339748
1.676238
-1.180133
H
-5.187859
2.615618
-1.010820
O
-6.168863
-0.973079
-0.522550
H
-6.633082
-0.416321
-1.160608
O
-2.791363
-0.876757
0.866918
C
-3.915246
-2.834393
0.167880
H
-3.499838
-3.392824
1.018584
H
-4.890605
-3.259774
-0.073586
O
-3.102808
-2.967814
-0.977962
H
-2.188857
-2.710343
-0.759601
C
0.664429
-0.453735
0.940947
C
-0.347497
0.619873
0.479379
C
0.348979
1.970939
0.312874
C
1.614406
1.858019
-0.527281
C
2.531895
0.803796
0.080635
H
0.954567
-0.227060
1.977583
H
-0.790447
0.298551
-0.464810
H
0.627134
2.336443
1.311197
H
1.360723
1.540355
-1.546254
H
2.849090
1.093967
1.092741
O
1.851609
-0.439047
0.114635
O
-0.550780
2.903522
-0.287921
H
-0.048997
3.706556
-0.484938
O
2.205898
3.151858
-0.536557
S17
H
O
C
C
C
C
C
C
H
H
H
H
H
C
H
H
O
H
O
H
H
2.949980
3.645354
7.266399
6.113825
4.879536
4.814987
5.963238
7.183266
8.219663
6.163612
3.985851
5.884537
8.073757
0.111473
0.897810
-0.724191
-0.375897
0.364729
1.955270
2.345035
2.633452
3.155205
0.678917
-0.925866
-1.171913
-0.660344
0.119814
0.368074
-0.157059
-1.331103
-1.776424
-0.888358
0.972239
0.040531
-1.878152
-2.560788
-1.935249
-2.270716
-2.514436
-2.519131
-1.776992
-3.188090
-1.150967
-0.758795
0.551892
1.291847
0.885628
-0.268432
-1.021536
-0.610173
0.873034
2.191638
1.452022
-1.918637
-1.197776
0.905463
1.250789
1.600511
-0.363843
-0.950971
-1.821601
-1.336105
-1.956891
S18
β-D-benzyl lactoside·H2O
Conformer 1
B3LYP/6-311+G*
Total energy: -1645.1619177 H
ZPE: 0.506236 H
MP2/6-311++G** // B3LYP/6-311+G*
Total energy: -1640.9236429 H
Cartesian coordinates:
C
-6.215064
-1.255380
-1.787086
C
-7.070186
-0.157074
-1.745710
C
-7.012675
0.724931
-0.665101
C
-6.106035
0.504857
0.367498
C
-5.240277
-0.595172
0.336059
C
-5.303451
-1.468798
-0.752318
C
-4.263853
-0.835570
1.464565
O
-3.279717
0.207068
1.615640
C
-2.366822
0.334940
0.569238
O
-1.569257
-0.834494
0.502242
C
-0.569508
-0.817376
-0.523264
C
0.377087
0.397036
-0.367016
C
-0.432640
1.680079
-0.207592
C
-1.474679
1.529238
0.888120
O
-2.195377
2.759930
0.927854
O
0.441524
2.772397
0.099592
O
1.161971
0.515350
-1.567946
C
2.552138
0.414416
-1.491506
C
3.228544
1.416104
-0.542651
C
4.736107
1.189788
-0.570498
C
5.088814
-0.248159
-0.197309
C
4.265075
-1.237215
-1.034428
O
2.879194
-0.911960
-1.087868
C
0.138513
-2.166679
-0.454124
O
0.820340
-2.349842
0.779972
O
3.010803
2.760701
-0.925742
O
5.394591
2.042275
0.359949
O
4.852585
-0.483951
1.189594
C
4.340991
-2.674301
-0.508913
O
3.617292
-2.862006
0.700313
O
0.723213
-0.529124
2.911723
H
-3.755192
-1.794015
1.339957
H
2.892874
0.594162
-2.519887
H
2.868374
1.243853
0.477241
H
5.103282
1.397062
-1.586210
H
6.152138
-0.421373
-0.414628
H
4.685258
-1.223312
-2.053829
H
5.393224
-2.959214
-0.382926
H
3.893720
-3.351603
-1.238173
H
2.096351
2.988366
-0.674005
H
4.982656
2.915139
0.288580
H
5.126697
0.305313
1.678537
H
3.946347
-2.210888
1.341586
H
-4.778474
-0.846759
2.427068
H
-2.891947
0.480362
-0.389119
H
-0.977171
1.333179
1.844675
H
-0.940591
1.894727
-1.157826
H
1.006207
0.249483
0.509456
H
-1.056166
-0.740879
-1.508730
H
0.829844
-2.244955
-1.293763
H
-0.624381
-2.946491
-0.553274
S19
H
H
H
H
H
H
H
H
H
H
-2.836448
-0.111635
1.770037
0.646230
0.105008
-7.779368
-7.679030
-6.067938
-4.635996
-6.253667
2.714041
3.510965
-2.524203
-1.241810
-0.741102
0.012358
1.580857
1.191870
-2.325081
-1.944806
1.647572
0.389300
0.634351
2.247767
3.618467
-2.549607
-0.626682
1.207906
-0.789684
-2.624507
Conformer 2
B3LYP/6-311+G*
Total energy: -1645.1665821 H
ZPE: 0.507679 H
MP2/6-311++G** // B3LYP/6-311+G*
Total energy: -1640.9248524 H
Cartesian coordinates:
C
5.589177
-0.850256
0.502515
C
5.287873
0.467271
0.143038
C
6.001196
1.068057
-0.898203
C
7.012548
0.373636
-1.560514
C
7.310594
-0.937859
-1.195413
C
6.592842
-1.547812
-0.166832
C
4.242657
1.265646
0.894611
O
3.158235
0.476085
1.404953
C
2.261889
0.008082
0.455305
O
1.356702
1.084962
0.166902
C
0.343097
0.806004
-0.813752
C
-0.518430
-0.383275
-0.350749
C
0.369963
-1.563773
0.049148
C
1.471443
-1.160385
1.027834
O
2.350308
-2.247472
1.257659
O
-0.342639
-2.613346
0.686595
O
-1.329886
-0.822183
-1.459163
C
-2.721575
-0.788916
-1.341498
C
-3.290090
-1.640212
-0.203771
C
-4.811108
-1.490279
-0.132300
C
-5.178359
-0.017045
0.058662
C
-4.506028
0.833592
-1.033373
O
-3.110179
0.563138
-1.166524
C
-0.434601
2.101972
-1.041971
O
-1.169650
2.545501
0.092190
O
-2.919887
-3.000260
-0.435107
O
-5.322757
-2.306921
0.915286
O
-4.801934
0.320329
1.388790
C
-4.595047
2.339469
-0.772948
O
-3.930930
2.708219
0.427796
O
0.855799
3.282865
1.806598
H
-3.084016
-1.174256
-2.303796
H
-2.870289
-1.301078
0.748407
H
-5.258665
-1.875041
-1.054716
H
-6.266696
0.097159
-0.051760
H
-5.016354
0.609614
-1.984837
H
-5.641891
2.635228
-0.666373
H
-4.176529
2.878181
-1.630137
H
-3.477745
-3.546261
0.138222
H
-5.215328
-1.811078
1.741533
H
-4.477866
1.241805
1.405316
H
-2.959489
2.657787
0.292598
H
3.854812
2.077379
0.270078
S20
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
4.680242
2.776464
1.014791
0.847017
-1.139164
0.826125
-1.154206
0.271690
1.797953
-1.076661
-0.565272
0.836258
1.311243
5.766732
7.558976
8.092351
6.813047
5.018769
1.720588
-0.285759
-0.829861
-1.943432
-0.064013
0.535185
1.937254
2.876405
-3.022411
-2.925392
2.943063
3.323470
2.464486
2.087225
0.853196
-1.483911
-2.572497
-1.333870
1.786738
-0.470427
1.971210
-0.867053
0.487857
-1.764727
-1.841795
-1.362319
1.430937
0.126485
0.751198
2.767822
1.545124
-1.194671
-2.366570
-1.713828
0.115457
1.287484
Conformer 3
B3LYP/6-311+G*
Total energy: -1645.1646891 H
ZPE: 0.506832 H
MP2/6-311++G** // B3LYP/6-311+G*
Total energy: -1640.9210460 H
Cartesian coordinates:
C
-5.357496
-1.695002
0.785188
C
-5.366544
-0.747111
-0.245051
C
-6.536548
-0.022473
-0.488519
C
-7.680043
-0.241731
0.278893
C
-7.661555
-1.187864
1.301743
C
-6.497131
-1.914207
1.554817
C
-4.122429
-0.502363
-1.053656
O
-3.254374
0.378965
-0.305137
C
-2.003972
0.599443
-0.896756
O
-1.282123
-0.615428
-0.854031
C
0.011370
-0.574647
-1.466736
C
0.899712
0.488571
-0.787050
C
0.152024
1.812802
-0.694428
C
-1.243813
1.659814
-0.097214
O
-1.819735
2.952532
-0.136854
O
0.897309
2.748240
0.093692
O
2.063732
0.699374
-1.609772
C
3.334230
0.458057
-1.087429
C
3.680914
1.256760
0.179162
C
5.092830
0.895863
0.627546
C
5.235887
-0.607005
0.857339
C
4.718622
-1.386300
-0.359911
O
3.446899
-0.934469
-0.812437
C
0.580155
-1.990423
-1.391943
O
0.786934
-2.407795
-0.058165
O
3.663147
2.655282
-0.033700
O
5.419598
1.544527
1.852398
O
4.519103
-1.007469
2.026089
C
4.569600
-2.887850
-0.095372
O
3.475177
-3.197788
0.754122
O
-4.050437
2.470164
1.388623
H
-4.360564
-0.028083
-2.013179
H
4.017818
0.742505
-1.898732
H
2.980512
0.983718
0.975567
H
5.799344
1.207807
-0.155328
S21
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
6.299906
5.462872
5.510758
4.376602
2.727407
5.105028
4.679656
3.583313
-3.588109
-2.136495
-1.165325
0.048218
1.172397
-0.095721
1.505234
-0.147900
-2.591821
0.304772
1.719021
-4.263214
-4.080530
-6.553734
-8.583207
-8.551552
-6.479419
-4.452003
-0.847426
-1.254002
-3.276155
-3.402872
2.929353
2.457218
-0.341517
-2.685008
-1.434724
0.924240
1.296701
2.217532
0.126353
-0.302876
-2.019440
-2.657337
2.982703
3.497458
-2.641099
2.406982
1.578273
0.717946
0.325146
-1.361855
-2.654856
-2.261735
0.989829
-1.163002
0.315726
-1.037781
-0.068466
1.784863
2.710085
1.570538
-1.245763
-1.943879
0.936040
-1.710621
0.205314
-2.529233
-1.971940
-1.869825
0.461876
0.255623
0.090273
2.324647
1.003913
-1.282976
0.077230
1.898097
2.347926
0.980815
Conformer 4
B3LYP/6-311+G*
Total energy: -1645.161397 H
ZPE: 0.506256 H
MP2/6-311++G** // B3LYP/6-311+G*
Total energy: -1640.9202028 H
Cartesian coordinates:
C
7.571381
-0.273540
0.294983
C
7.745048
0.613490
1.356667
C
6.738779
1.526889
1.669684
C
5.563401
1.552470
0.922165
C
5.378226
0.666400
-0.144297
C
6.393247
-0.246596
-0.449681
C
4.092164
0.671706
-0.924331
O
3.144289
-0.179344
-0.242202
C
1.952102
-0.405061
-0.932534
O
1.204824
0.806713
-0.939189
C
-0.058846
0.713297
-1.615097
C
-0.953304
-0.329293
-0.913970
C
-0.207460
-1.659222
-0.888846
C
1.159254
-1.508149
-0.222128
O
1.781653
-2.777357
-0.294840
O
-0.971713
-2.649050
-0.201323
O
-2.152395
-0.465783
-1.678967
C
-3.375470
-0.243736
-1.021029
C
-3.757655
-1.323217
-0.001524
C
-5.142064
-0.984257
0.540909
C
-5.129795
0.396334
1.208183
C
-4.515467
1.444504
0.265633
O
-3.302577
0.995270
-0.350229
C
-0.626423
2.125365
-1.671707
O
-0.784187
2.726700
-0.392283
O
-3.811808
-2.626264
-0.556671
O
-5.553852
-1.932480
1.521412
S22
O
C
O
O
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
H
-4.394745
-4.158620
-3.543275
3.703159
4.245716
-4.113476
-3.037211
-5.861155
-6.167427
-5.245720
-3.519607
-5.075497
-2.891651
-5.297881
-4.655952
-2.627604
3.674808
2.170189
1.022653
-0.055380
-1.176322
0.101701
-1.616213
0.031154
2.485666
-0.371673
0.066462
3.868006
4.547023
8.663179
6.871146
4.782064
6.262174
8.354868
0.342899
2.746986
3.688706
-2.259771
0.283352
-0.213217
-1.295408
-0.982432
0.696101
1.656340
2.511449
3.206152
-2.928398
-2.807115
-0.475456
3.405148
1.678317
-0.701186
-1.202256
-1.990980
0.011412
0.381926
2.101514
2.738755
-2.824754
-3.391363
2.729710
-1.397243
-2.624207
0.596554
2.221144
2.265696
-0.936948
-0.980748
2.423782
0.986877
0.130093
1.603613
-1.938020
-1.834296
0.822101
-0.291237
1.417021
-0.530299
1.841956
1.366184
-0.635220
1.196231
2.870216
-0.024333
-0.999752
-1.972279
0.823339
-1.926190
0.098447
-2.652890
-2.123146
-2.300090
0.381308
-0.035797
0.063404
1.190641
1.887687
1.934946
2.493036
1.167378
-1.278142
0.042495
S23
3. Complete reference 21.
Frisch, M. J.; Trucks, G. W.; Schlegel, H. B.; G.E. Scuseria; Robb, M. A.; Cheesemam, J. R.; J.A.
Montgomery, J.; Vreven, T.; Kudin, K. N.; Burant, J. C.; Millam, J. M.; Lyengar, S. S.; Tomasi,
J.; Barone, V.; Mennucci, B.; Cossi, M.; Scalmani, G.; Rega, N.; Petersson, G. A.; Nakatsuji,
H.; Hada, M.; Ehara, M.; K. Toyota; Fukuda, R.; Hasegawa, J.; Ishida, M.; Nakajima, T.;
Honda, Y.; Kitao, O.; Nakai, H.; Klene, M.; Li, X.; Knox, J. E.; Hratchian, H. P.; Cross, J. B.;
Adamo, C.; Jaramillo, J.; Gomperts, R.; Stratmann, R. E.; Yazyev, O.; Austin, A. J.; Cammi, R.;
Pomelli, C.; Ochterski, J. W.; Ayala, P. Y.; Morokuma, K.; Voth, G. A.; Salvador, P.;
Dannenberg, J. J.; Zakrzewski, V. G.; Dapprich, S.; Daniels, A. D.; Strain, M. C.; Farkas, O.;
Malick, D. K.; Rabuck, A. D.; Raghavachari, K.; Foresman, J. B.; Ortiz, J. V.; Cui, Q.; Baboul, A.
G.; Clifford, S.; Cioslowski, J.; Stefanov, B. B.; Liu, G.; Liashenko, A.; Piskorz, P.; Komaromi, I.;
Martin, R. L.; Fox, D. J.; Keith, T.; Al-Laham, M. A.; Peng, C. Y.; Nanayakkara, A.;
Challacombe, M.; Gill, P. M. W.; Johnson, B.; Chen, W.; Wong, M. W.; Gonzalez, C.; Pople, J.
A. Gaussian 03, Revision B.03, Pittsburgh PA, 2003.