Structural Preferences and Vibrational Analysis of 2-Hydroxy-2-methyl-1-phenylpropan-1-one: A Computational and Infrared Spectroscopic Research
Table 1
Optimized geometry of 2-hydroxy-2-methyl-1-phenylpropan-1-one calculated at HF and B3LYP using 6-311+G** basis set.
Internal coordinates
Level of theory
RHF/6-311+G**
DFT/6-311+G**
X-raya
Bond lengths (Å)
C1C2
1.395
1.405
1.39
C2C3
1.381
1.388
1.41
C3C4
1.386
1.395
1.37
C4C5
1.383
1.392
1.36
C5C6
1.385
1.392
1.42
C6C1
1.390
1.402
1.39
1.073
1.082
C1C12
1.506
1.499
1.48
C12O13
1.194
1.221
1.24
C12C14
1.547
1.554
1.55b
C14C15
1.535
1.540
1.54b
C15H16
1.082
1.090
C15H17
1.085
1.092
C15H18
1.084
1.092
C14C19
1.531
1.540
1.54b
C19H20
1.084
1.092
C19H21
1.085
1.092
C19H22
1.081
1.090
C14O23
1.399
1.421
1.38b
O23H24
0.944
0.971
0.95
Bond angles (°)
C1C2C3
120.8
120.9
120
C2C3C4
119.9
120.0
122
C3C4C5
119.7
119.7
118
C4C5C6
120.1
120.2
123
C5C6C1
120.6
120.6
118
C6C1C2
118.5
118.4
119
CCHring average
119.4
119.3
C6C1C12
125.1
124.8
C1C12O13
118.7
119.2
118
C1C12C14
124.0
123.9
C12C14C15
110.5
111.3
C14C15H16
113.6
113.4
C14C15H17
110.0
110.1
C14C15H18
108.0
107.9
C12C14C19
112.3
111.3
C14C19H20
107.9
107.9
C14C19H21
110.2
110.1
C14C19H22
113.4
113.4
C12C14O23
107.4
107.2
C14O23H24
109.0
106.2
111
Dihedral angles (°)
C1C2C3C4
0.4
0.0
C2C3C4C5
0.0
C3C4C5C6
0.0
C6C4C2H7
179.7
180.0
C1C2C3H8
180.0
C2C3C4H9
179.8
180.0
C3C4C5H10
179.7
180.0
C4C5C6H11
179.9
180.0
C5C6C1C12
179.2
C6C1C12O13
179.9
C6C1C12C14
10.7
0.0
C1C12C14C15
C12C14C15H16
C12C14C15H17
C12C14C15H18
C1C12C14C19
C12C14C19H20
C12C14C19H21
C12C14C19H22
C1C12C14O23
C12C14O23H24
11.2
0.0
XRD data of closely related molecules benzoic acid and butyric acid [5, 6].
bXRD data of 4-butyl-1-(4-hydroxyphenyl)-2-phenyl-3,5-pyrazolidinedione [7].