Table_ISM.doc 14KB Jun 05 2011 09:30:50 PM
Supplementary Material for:
MMFF VI. The MMFF94s Option for Energy
Minimization Studies.
THOMAS A. HALGREN
Molecular Systems, Merck Research Laboratories, P.O. Box 2000, Rahway, NJ 07065
TABLE I-SM. _________________________________________
Observed and Calculated Pyramidalization at Trigonal Delocalized Nitrogen
Average Wilson angle (deg.)
Category
refcodea
Observed
MMFF94
MMFF94s
1° amides
ACEMID03
7
14
0
ASPARM06
0
40
17
BZAMID02
18
23
5
FACET01
1
0
0
FEHDAX01
3
14
2
SECAZC02
9
37
0
UREAOH12
4
39
10
UREAXX08
0
41
0
UROXAL01
4
41
0
8
41
0
THACEM01
0
0
0
THIOUR04
4
32
0
1° ureas
"
1° acyclic thioamides
1° aromatic amines and nucleic acid bases
ADENOS01
9
40
1
AMBACO07
51
44
14
MEADEN02
16
40
0
MELAMI04
14
46
0
"
17
47
0
"
38
46
0
41
59
48
CYGUAN01
14
40
3
AMCLPY11
1
53
33
FORAMO01
20
43
0
NTRGUA01
0
48
9
4
48
15
GLYGLY04
6
44
30
HIPPAC02
3
26
5
NALCYS02
1
12
5
SECAZC02
40
39
0
CBOATZ02
7
35
9
CYGUAN01
36
25
13
UREAOH12
15
32
10
9
16
4
3
16
4
DAHBAP
4
9
2
DOTREJ
4
9
3
FEPLOB
14
4
5
GAMGUW
2
1
1
JAMREU
1
14
2
OPHDAH01
1° amidines and guanidines
"
2° amides and ureas
2° amidines and guanidines
2° hydroxamic acids
3° acyclic amides
CIXWEL
"
JEDYOG
3
10
2
SICYAE
0
7
1
VENXIV
3
11
4
BISMEV02
12
22
11
BOCGLP02
2
4
2
17
18
5
DIRCAI
2
21
11
DOTREJ
4
16
3
1
6
1
DUVNAJ
6
4
3
FAMDUS
6
3
2
FAMFEE
5
6
4
FIFCEC
14
21
13
"
18
10
7
"
17
9
7
"
2
23
13
FIWNUU
7
8
7
FIWPAC
11
7
4
GICSOA
20
17
3
KODFUE
1
0
0
KOJPII
4
5
3
SEJSIJ
11
22
14
"
0
0
0
CIRZUY
3
16
3
DECKUR
28
25
14
DECLAY
31
30
21
DESPUM
1
17
12
16
17
8
29
22
12
FEPLOB
7
11
4
FETXUX
2
18
6
0
24
10
3° 5-ring amides
DEKRUG
"
3° 6-ring amides
DINSUO10
"
"
FEVNUP
15
18
10
FUSHIK
19
27
19
GEYBUH
13
4
3
GICSOA
2
11
3
8
10
6
10
3
2
3
11
4
JIYVES
15
20
8
KASPID
3
20
1
SAFWOL
1
20
3
SAFWUR
1
20
2
VAXROB
11
22
1
KEXXUG
0
14
2
KEXYAN
8
15
4
COXMAD
20
29
17
CUCKOA
18
20
12
FIVXUD
4
0
1
FIYYUH
0
27
0
GIMJUH
3
15
7
JISDUK
3
14
8
KASKIY
22
31
18
KASNOH
3
18
0
KOHJUM
2
11
6
SIMDUN
48
41
36
VEBFIR
43
39
34
JODTOL
11
22
2
JODTUR
11
22
2
JODVAZ
10
22
2
"
GOJPUQ
HYTPRD01
3° 8-ring amides
3° bicyclic amides
3° acyclic ureas
3° cyclic ureas
FETXUX
13
0
6
SACVOH
26
26
19
JEHWIC
1
1
1
KICROD
38
32
25
33
32
25
DAHBAP
3
5
3
ETHUSS02
3
2
2
METHUS03
1
4
2
SICYEI
5
17
3
FENJOX
1
8
4
JABCIY
1
18
9
JEFRAN
1
15
1
COTXEO
2
19
2
CUFJUI
1
15
1
FURJAD
0
5
4
3
5
4
44
40
33
4
25
13
CIZYEP
11
15
7
DICYOD
3
1
1
JOFTED
3
2
1
KENCOV
2
12
4
3° bicyclic ureas
"
3° 6-ring hydroxamic acids
3° acyclic thioamides
3° acyclic thioureas
3° cyclic thioamides
"
3° bicyclic thioureas
FENJIR
3° acyclic enamines
BYITOT02
MNETAN01
4
17
5
BUKJOG10
16
25
0
DEFTUD
3
21
8
DEFVAL
1
18
8
DIXJEZ
1
29
0
DIWWEL
45
44
33
DMAFBZ01
13
26
0
DOCXUA
22
25
2
FAVCOU
7
21
6
FAWWIJ
15
42
8
FUMVIS
1
34
8
FUVNEP
2
26
2
GAKSAM
0
24
0
GILYOP
42
26
0
JEXREJ
1
26
2
KAHTOC
4
38
0
"
20
38
0
"
22
38
0
10
24
2
MPABZS02
4
26
2
PDABZA01
0
26
0
SEJNEA
7
15
8
VEJCIW
0
10
0
VEKMON
2
0
0
VUXKAA
2
20
7
COBMUB
33
44
29
CUZJOW
23
30
14
DEGRIQ
56
50
46
50
50
46
FIFZID
16
32
17
JITMII
27
19
10
KIHVEC
15
42
28
3° aromatic amines
KEZYET
3° cyclic/bicyclic aromatic amines
"
3° cyclic enamines
DARDEF
44
33
19
DARDIJ
44
33
22
DARDOP
33
20
9
DECKUR
5
13
6
DECLAY
3
14
8
DUWRES
39
34
2
0
12
6
KOKMIG
10
18
3
PIMTAZ01
44
42
27
SAWJIJ
43
43
27
SICGAM
44
39
29
SEMWEM
20
30
9
SICGAM
16
30
17
VATCOI
16
24
12
VAXROB
43
40
27
VEHZOX
7
30
9
CUZDOQ
4
18
6
DUPHIF
7
22
9
9
2
0
2
15
9
1
21
8
8
29
18
14
22
5
SAPMUR
1
22
10
SAYNIP
9
14
8
VUYKUV
2
21
10
GESSUS
33
36
36
JAVGES
14
20
20
JINYAG
43
41
41
KIBDII
3° guanidines/amidines
"
JEFRAN
"
PHOSLB10
"
3° acyclic sulfonamides
3° 6-ring sulfonamides
KAVSOP
40
38
38
VOGKIL
42
40
40
20
26
26
30
26
26
3° large-ring sulfonamides
SACTUL
“
a
Entry in the Cambridge Structural Database.
MMFF VI. The MMFF94s Option for Energy
Minimization Studies.
THOMAS A. HALGREN
Molecular Systems, Merck Research Laboratories, P.O. Box 2000, Rahway, NJ 07065
TABLE I-SM. _________________________________________
Observed and Calculated Pyramidalization at Trigonal Delocalized Nitrogen
Average Wilson angle (deg.)
Category
refcodea
Observed
MMFF94
MMFF94s
1° amides
ACEMID03
7
14
0
ASPARM06
0
40
17
BZAMID02
18
23
5
FACET01
1
0
0
FEHDAX01
3
14
2
SECAZC02
9
37
0
UREAOH12
4
39
10
UREAXX08
0
41
0
UROXAL01
4
41
0
8
41
0
THACEM01
0
0
0
THIOUR04
4
32
0
1° ureas
"
1° acyclic thioamides
1° aromatic amines and nucleic acid bases
ADENOS01
9
40
1
AMBACO07
51
44
14
MEADEN02
16
40
0
MELAMI04
14
46
0
"
17
47
0
"
38
46
0
41
59
48
CYGUAN01
14
40
3
AMCLPY11
1
53
33
FORAMO01
20
43
0
NTRGUA01
0
48
9
4
48
15
GLYGLY04
6
44
30
HIPPAC02
3
26
5
NALCYS02
1
12
5
SECAZC02
40
39
0
CBOATZ02
7
35
9
CYGUAN01
36
25
13
UREAOH12
15
32
10
9
16
4
3
16
4
DAHBAP
4
9
2
DOTREJ
4
9
3
FEPLOB
14
4
5
GAMGUW
2
1
1
JAMREU
1
14
2
OPHDAH01
1° amidines and guanidines
"
2° amides and ureas
2° amidines and guanidines
2° hydroxamic acids
3° acyclic amides
CIXWEL
"
JEDYOG
3
10
2
SICYAE
0
7
1
VENXIV
3
11
4
BISMEV02
12
22
11
BOCGLP02
2
4
2
17
18
5
DIRCAI
2
21
11
DOTREJ
4
16
3
1
6
1
DUVNAJ
6
4
3
FAMDUS
6
3
2
FAMFEE
5
6
4
FIFCEC
14
21
13
"
18
10
7
"
17
9
7
"
2
23
13
FIWNUU
7
8
7
FIWPAC
11
7
4
GICSOA
20
17
3
KODFUE
1
0
0
KOJPII
4
5
3
SEJSIJ
11
22
14
"
0
0
0
CIRZUY
3
16
3
DECKUR
28
25
14
DECLAY
31
30
21
DESPUM
1
17
12
16
17
8
29
22
12
FEPLOB
7
11
4
FETXUX
2
18
6
0
24
10
3° 5-ring amides
DEKRUG
"
3° 6-ring amides
DINSUO10
"
"
FEVNUP
15
18
10
FUSHIK
19
27
19
GEYBUH
13
4
3
GICSOA
2
11
3
8
10
6
10
3
2
3
11
4
JIYVES
15
20
8
KASPID
3
20
1
SAFWOL
1
20
3
SAFWUR
1
20
2
VAXROB
11
22
1
KEXXUG
0
14
2
KEXYAN
8
15
4
COXMAD
20
29
17
CUCKOA
18
20
12
FIVXUD
4
0
1
FIYYUH
0
27
0
GIMJUH
3
15
7
JISDUK
3
14
8
KASKIY
22
31
18
KASNOH
3
18
0
KOHJUM
2
11
6
SIMDUN
48
41
36
VEBFIR
43
39
34
JODTOL
11
22
2
JODTUR
11
22
2
JODVAZ
10
22
2
"
GOJPUQ
HYTPRD01
3° 8-ring amides
3° bicyclic amides
3° acyclic ureas
3° cyclic ureas
FETXUX
13
0
6
SACVOH
26
26
19
JEHWIC
1
1
1
KICROD
38
32
25
33
32
25
DAHBAP
3
5
3
ETHUSS02
3
2
2
METHUS03
1
4
2
SICYEI
5
17
3
FENJOX
1
8
4
JABCIY
1
18
9
JEFRAN
1
15
1
COTXEO
2
19
2
CUFJUI
1
15
1
FURJAD
0
5
4
3
5
4
44
40
33
4
25
13
CIZYEP
11
15
7
DICYOD
3
1
1
JOFTED
3
2
1
KENCOV
2
12
4
3° bicyclic ureas
"
3° 6-ring hydroxamic acids
3° acyclic thioamides
3° acyclic thioureas
3° cyclic thioamides
"
3° bicyclic thioureas
FENJIR
3° acyclic enamines
BYITOT02
MNETAN01
4
17
5
BUKJOG10
16
25
0
DEFTUD
3
21
8
DEFVAL
1
18
8
DIXJEZ
1
29
0
DIWWEL
45
44
33
DMAFBZ01
13
26
0
DOCXUA
22
25
2
FAVCOU
7
21
6
FAWWIJ
15
42
8
FUMVIS
1
34
8
FUVNEP
2
26
2
GAKSAM
0
24
0
GILYOP
42
26
0
JEXREJ
1
26
2
KAHTOC
4
38
0
"
20
38
0
"
22
38
0
10
24
2
MPABZS02
4
26
2
PDABZA01
0
26
0
SEJNEA
7
15
8
VEJCIW
0
10
0
VEKMON
2
0
0
VUXKAA
2
20
7
COBMUB
33
44
29
CUZJOW
23
30
14
DEGRIQ
56
50
46
50
50
46
FIFZID
16
32
17
JITMII
27
19
10
KIHVEC
15
42
28
3° aromatic amines
KEZYET
3° cyclic/bicyclic aromatic amines
"
3° cyclic enamines
DARDEF
44
33
19
DARDIJ
44
33
22
DARDOP
33
20
9
DECKUR
5
13
6
DECLAY
3
14
8
DUWRES
39
34
2
0
12
6
KOKMIG
10
18
3
PIMTAZ01
44
42
27
SAWJIJ
43
43
27
SICGAM
44
39
29
SEMWEM
20
30
9
SICGAM
16
30
17
VATCOI
16
24
12
VAXROB
43
40
27
VEHZOX
7
30
9
CUZDOQ
4
18
6
DUPHIF
7
22
9
9
2
0
2
15
9
1
21
8
8
29
18
14
22
5
SAPMUR
1
22
10
SAYNIP
9
14
8
VUYKUV
2
21
10
GESSUS
33
36
36
JAVGES
14
20
20
JINYAG
43
41
41
KIBDII
3° guanidines/amidines
"
JEFRAN
"
PHOSLB10
"
3° acyclic sulfonamides
3° 6-ring sulfonamides
KAVSOP
40
38
38
VOGKIL
42
40
40
20
26
26
30
26
26
3° large-ring sulfonamides
SACTUL
“
a
Entry in the Cambridge Structural Database.