Vibrational Spectroscopy Investigation Using Ab Initio and Density Functional Theory Analysis on the Structure of tert-Butyl 3a-Chloroperhydro-2,6a-epoxyoxireno[e]isoindole-5-carboxylate
Table 2
Optimized and experimental geometries of the title compound in the ground state.
Parametersa,b
Experimentalc
Calculated
6-31G(d)
6-31G(d,p)
6-31G(d)
6-31G(d,p)
6-31G(d)
6-31G(d,p)
Bond lengths (Å)
R (10,16)
1.800 (2)
1.806
1.807
1.865
1.865
1.834
1.834
R (11,15)
1.210 (3)
1.199
1.200
1.235
1.235
1.222
1.223
R (12,19)
1.446 (3)
1.411
1.410
1.459
1.459
1.438
1.439
R (12,21)
1.432 (2)
1.409
1.409
1.457
1.458
1.436
1.437
R (13,15)
1.339 (3)
1.351
1.349
1.378
1.379
1.364
1.365
R (13,18)
1.459 (3)
1.456
1.458
1.479
1.481
1.467
1.466
R (13,22)
1.453 (3)
1.454
1.455
1.476
1.477
1.462
1.463
R (14,20)
1.442 (3)
1.401
1.401
1.453
1.454
1.433
1.432
R (14,25)
1.440 (3)
1.401
1.401
1.452
1.452
1.431
1.431
R (15,17)
1.342 (3)
1.325
1.325
1.378
1.378
1.357
1.356
R (16,21)
1.548 (3)
1.549
1.550
1.580
1.579
1.566
1.566
R (16,22)
1.514 (3)
1.532
1.530
1.547
1.547
1.536
1.535
R (16,24)
1.538 (3)
1.550
1.549
1.566
1.566
1.553
1.554
R (17,23)
1.463 (3)
1.448
1.449
1.495
1.496
1.472
1.472
R (18,21)
1.501 (3)
1.512
1.512
1.525
1.526
1.516
1.517
R (19,24)
1.536 (4)
1.547
1.547
1.567
1.568
1.556
1.556
R (19,25)
1.509 (4)
1.527
1.526
1.547
1.548
1.535
1.536
R (20,21)
1.516 (3)
1.526
1.524
1.545
1.545
1.533
1.532
R (20,25)
1.450 (3)
1.449
1.449
1.480
1.480
1.467
1.468
R (23,26)
1.508 (4)
1.526
1.525
1.543
1.541
1.531
1.531
R (23,30)
1.502 (4)
1.527
1.526
1.543
1.543
1.531
1.531
R (23,34)
1.502 (4)
1.527
1.527
1.544
1.542
1.532
1.532
0.9868
0.9871
0.9961
0.9962
0.9951
0.9950
Bond angles (°)
A (19,12,21)
96.88 (15)
99.0
99.0
97.6
97.6
98.0
98.0
A (15,13,18)
120.21 (17)
120.1
120.1
120.0
119.7
120.0
119.9
A (15,13,22)
127.19 (17)
125.5
125.6
126.1
126.3
126.0
126.3
A (18,13,22)
112.59 (16)
114.1
114.0
113.8
113.3
113.8
113.6
A (11,15,13)
123.6 (2)
122.9
122.9
123.0
122.9
123.1
122.9
A (11,15,17)
125.62 (19)
125.7
125.7
127.1
127.0
126.6
126.5
A (13,15,17)
110.82 (18)
111.3
111.4
109.9
110.1
110.4
110.6
A (10,16,21)
110.36 (14)
112.7
112.7
112.2
112.0
112.2
112.1
A (10,16,22)
108.77 (16)
109.5
109.6
109.2
109.1
109.4
109.3
A (10,16,24)
113.45 (17)
113.0
112.9
112.4
112.4
112.7
112.8
A (21,16,22)
101.95 (16)
101.7
101.7
102.0
101.8
101.8
101.6
A (21,16,24)
102.96 (17)
102.2
102.2
102.7
102.7
102.5
102.5
A (22,16,24)
118.4 (2)
117.0
117.0
117.8
118.1
117.4
117.8
A (15,17,23)
120.50 (18)
122.7
122.7
120.2
120.1
120.8
120.7
A (13,18,21)
103.57 (16)
102.8
102.8
103.3
103.5
103.2
103.3
A (12,19,24)
102.19 (18)
101.7
101.7
101.9
101.8
101.9
101.9
A (12,19,25)
101.94 (19)
101.9
101.9
102.1
102.1
102.0
102.1
A (24,19,25)
107.8 (2)
107.2
107.2
107.6
107.4
107.3
107.2
A (14,20,21)
114.0 (2)
113.1
113.1
113.7
113.6
113.5
113.5
A (21,20,25)
102.9 (2)
102.8
102.8
103.0
103.0
102.8
102.9
A (12,21,16)
99.80 (15)
98.7
98.6
98.5
98.4
98.8
98.7
A (12,21,18)
112.54 (17)
112.2
112.2
111.6
111.7
111.8
111.9
A (12,21,20)
102.24 (16)
102.2
102.3
102.4
102.5
102.5
102.5
A (16,21,18)
106.95 (16)
106.7
106.7
106.8
106.8
106.7
106.7
A (16,21,20)
108.39 (16)
109.9
109.9
109.6
109.7
109.4
109.5
A (18,21,20)
124.24 (19)
124.3
124.2
124.8
124.7
124.7
124.5
A (13,22,16)
103.32 (17)
103.2
103.2
103.7
103.7
103.6
103.5
A (17,23,26)
102.1 (2)
102.6
102.6
102.1
102.1
102.4
102.5
A (17,23,30)
110.0 (2)
110.3
110.3
109.8
110.0
109.9
110.1
A (17,23,34)
110.0 (2)
110.3
110.2
110.1
109.7
110.2
109.9
A (26,23,30)
111.1 (3)
110.4
110.5
111.0
110.9
110.8
110.8
A (26,23,34)
110.5 (3)
110.5
110.6
110.8
111.0
110.7
110.8
A (30,23,34)
112.7 (3)
112.3
112.3
112.6
112.5
112.4
112.3
A (16,24,19)
100.05 (3)
99.8
99.9
100.2
100.3
100.2
100.2
A (19,25,20)
104.00 (19)
103.6
103.6
103.7
103.7
103.6
103.6
0.9929
0.9929
0.9961
0.9966
0.9964
0.9969
aThe atom numbering scheme of the molecular structure is given in Figure 2(a).
br: correlation coefficient between optimized and experimental geometrical parameters.
cFrom [10].
